The Official SaaStr Podcast: SaaS | Founders | Investors

Karen Peacock is COO of Intercom, one of the fastest growing SaaS businesses of all time. She has led businesses of all sizes through massive growth. Listen to her top 5 lessons learned building and scaling SaaS businesses from $1M to $500M in ARR including expanding to serve upmarket customers, moving from product to platform, and hiring to drive breakthrough customer experiences and business growth. Missed the session? Here’s what Karen talks about: How should you expand your market? How to move upmarket The steps to building a product and creating an end to end experience If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin SaaStr Karen Peacock This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Ben Braverman is the CRO @ Flexport, one of the world’s fastest growing startups combining technology, infrastructure and expertise, to build the operating system for global trade. To date they have $1.35Bn in funding from some of the biggest and best in the business including Softbank’s Vision Fund, Founders Fund, DST, Susa Ventures and Y Combinator, just to name a few. As for Ben, he spearheads global sales and go to market teams. Prior to Flexport, Ben helped drive two high-growth companies to successful acquisitions: URX (acquired by Pinterest) and Heyzap (acquired by Fyber). In Today’s Episode We Discuss: How Ben made his way into the world of startups and came to be CRO of one of the world’s fastest growing startups in the form of Flexport? Why does Ben fundamentally disagree with the specialisation of roles within SaaS companies? What does he believes this does to the customer journey and relationship? How should one thing about role segmentation and allocation of accounts with this in mind? Where does Ben see many people going wrong here? Why does Ben believe it is “total horseshit to say the best sellers don’t make the best managers”? What must founders try and figure out before hiring their sales leader? What are the leading indicators that suggest a sales rep has the ability to be a sales manager? How does Ben determine between a stretch VP and a stretch too far? What does Ben mean when he says, “there are 3 distinct buckets of sales management”? What are they and what is their relationship between one another? Why does Ben believe one does not need sales management in the early days? What is the best way to train reps and determine payback period fast? Why does Ben believe sales ops is the most underappreciated role in the valley? 60 Second SaaStr: What does Ben know now that he wishes she had known at the beginning? What is the optimal relationship between CRO and CEO? What does Ben believe in SaaS that most around his disbelieve? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Ben Braverman This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Mark Roberge is a senior lecturer with Harvard Business School, former CRO of Hubspot and author of the bestseller "The Sales Acceleration Formula". Join him as he takes you through his step by step guide to revenue growth. Missed the session? Here’s what Mark talks about: An in-depth guide to driving revenue growth by company stage When to scale and how fast Product market fit, go-to market fit during the experiment stages If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin SaaStr Mark Roberge This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Leyla Seka is the executive vice president of the Salesforce Mobile platform experience. Over Leyla’s incredible 11 year journey with Salesforce she has seen the team scale from 1,800 to over 40,000 and revenue scale from $500m to over $16Bn. In Leyla’s role today, she leads the charge on extending the power of Salesforce with a full portfolio of mobile apps, and is responsible for driving product, go-to-market and other key programs around Salesforce’s mobile offerings. Prior to her current role, Leyla was executive vice president of the Salesforce AppExchange, where she launched a refreshed AppExchange storefront, a new partner program, and built an entire AppExchange-focused team, resulting in more than 4,000 solutions, installed nearly 6 million times. Beyond her day-to-day role, Leyla is also the executive sponsor of BOLDforce, Salesforce’s organization for expanding and empowering the black community at Salesforce. In Today’s Episode We Discuss: How Leyla made her way into the world of SaaS with Salesforce when it had 1,800 people and $500m in revenue? What were Leyla’s biggest learnings on people and business model through seeing the first hand hyper-scaling of Salesforce from $500m to $16Bn? How did Leyla evolve and scale as a leader herself in those 11 years? What advice does Leyla give to young people considering whether to found a startup, join a startup or join a hyper-growth company? Where do things start to break in the scaling of SaaS companies? What needs to be put in place to prepare for hyper-scale? What are the commonalities of where many founders go wrong in the scaling process? What does Leyla mean when she says, “growing up in product, you have to lead through influence”? How does Leyla think this influence can be created and maintained? How does Leyla think about the balance between effective influence and excessive influence? Why does Leyla believe that, “you can teach skills but you cannot teach empathy”? What have been her learnings from scaling teams when it comes to hiring and detecting candidates with true empathy? What can one do to nurture that empathy in the culture of the company? 60 Second SaaStr: What does Leyla know now that she wishes she had known at the beginning? What is the hardest element of Leyla’s role at Salesforce today? What does Leyla believe in SaaS that most around her disbelieve? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Leyla Seka This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

At Atlassian, openness is core to everything the company does: employees can access most information on Confluence; "open company, no b******t" is one of the company’s five values. But it can be risky. Atlassians knew the company was going public four months before it filed. The entire company was told about Atlassian selling its chat products Stride and Hipchat to its largest competitor in the space, Slack, four days before the news went out. Some would say that that level of openness is unnecessary, but Atlassian believes that trust and honesty are essential to maintaining the culture its worked so hard to build. Missed the session? Here’s what Jay talks about: What is driving growth in the cloud? Does collaboration help founders drive growth forward? How do you scale an open culture? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin SaaStr This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Jeff Lawson is the Founder & CEO @ Twilio, the company building the future of communications allowing you to engage customers like never before on voice, SMS, WhatsApp or Video. Prior to their IPO in 2016, Twilio had raised over $250m in VC funding from some of the best in venture including USV, Bessemer, Salesforce and Techstars just to name a few. As for Jeff, prior to founding Twilio, Jeff was the Founder & CTO @ Nine Star Inc and enjoyed a spell at Amazon as a Technical Product Manager. Sameer Dholakia is the CEO @ SendGrid, the category leader in email delivery, reaching half of the world’s digital users every 3 months. Last year Twilio acquired SendGrid bringing email into one seamless customer engagement platform. As for Sameer, prior to joining SendGrid, he spent 4 years at Citrix, where he drove the company’s product strategy for cloud infrastructure and server virtualization. Sameer joined the company in 2010, when Citrix acquired VMLogix, where he served as CEO and doubled revenues during each year of his tenure. Before that, he worked for 12 years at Trilogy, where he held key leadership roles helping the company grow from a start-up to a $300 million business. In Today’s Episode We Discuss: How Jeff came to found Twilio and what was that a-ha moment for him? How did Sameer enter the world of SaaS and come to be CEO @ SendGrid? How did Jeff and Sameer assess the culture fit between the 2 companies when deciding whether or not to join forces? How did they formulate and approach creating a new set of values with the 2 companies coming together? How do they distinguish between culture and values? How can leaders both be authoritative and vulnerable simultaneously? What does Jeff mean when he says, “the developer first approach is a maturation of the supply chain of software”? How has Jeff seen his original thesis for “developer first” evolve and change with time? What does truly special customer experience look like in the developer first model? In terms of product strategy, how do Jeff and Sameer approach when is the right time to release a second product? What does Jeff mean when he says, “you have to maximise the number of at bat opportunities you have”? Why does Sameer think that SendGrid waited too long to release additional product lines? What were his core learnings from that? How do Jeff and Sameer think about what what truly special leadership looks like today? How do they approach speaking so that people will remember? What are some of their biggest tips to aspiring entrepreneurs with regards to that and team empowerment? Why do both Jeff and Sameer believe that so much of the management wisdom today is outdated? 60 Second SaaStr: What do Jeff and Sameer know now that they wish they had known at the beginning? The book they have gifted most often and why? What does it take to truly be a great board member? What do the next 5 years look like for Twilio? How big could it get? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Jeff Lawson Sameer Dholakia This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Formerly a senior leader at Google, Claire Hughes Johnson is now Chief Operating Officer at Stripe, where she’s helped guide the online payments firm through rapid growth. Stripe today has more than 1,400 employees and processes billions of dollars for millions of users worldwide. Scaling the company’s employee base, sales teams, marketing, and operations—all while preserving its culture—has required a laser focus on first principles, smart processes, and effective hiring. Missed the session? Here’s what Claire talks about: How to avoid trapdoor decisions when scaling Lessons for scaling high-growth organizations If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin SaaStr This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Dan Reich is the Founder & CEO @ Troops.ai, the startup that is the ultimate slackbot for sales teams. To date, Dan has raised over $17m in VC funding with Troops from many friends of the show including Felicis Ventures, Founder Collective, First Round, Nextview, Susa Ventures and even Slack. As for Dan, he is also the Co-Founder and President of TULA, a private equity backed health and beauty business that has developed the world's first line of probiotic skincare products. Before that, Dan was a Co-Founder of Spinback (acquired by Buddy Media in May 2011, then acquired by Salesforce in June 2012). In Today’s Episode We Discuss: How Dan made his way into the world of SaaS with the founding of Spinback? How that led to his founding of the ultimate slackbot for sales teams in Troops? What does Dan really mean when he says “account based collaboration”? What is this a transition from? In terms of tracking and analysis, how does this change when making the move from tracking individual performance to team performance around an account? What can one do to actively implement this? What is key to a successful transition to this style of selling? What does Dan mean when he says, “sales teams are not working together the way we think they are”? What can sales leaders do to actively ensure their sales team is acting in unison? Where do many sales leaders go wrong here? How does Dan think about post mortems when an account is lost or won? How does Dan prevent dips in morale when sharing the loss of a sale? With scaling orgs, siloes are often created, why does Dan think many silos come into existence? At what stage does Dan really see them become a problem and cracks in the org begin to show? What can leaders do to instantly reduce the effect of silos? How does Dan think about controlling the noise to action ratio with the firehose of data at our disposal today? Dan’s 60 Second SaaStr: What does Dan know now that he wishes he had known at the beginning? What is the right time to train your sales team? The right way to structure sales comp plans? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Dan Reich This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Qualtrics Co-Founder and CEO Ryan Smith sits down with SaaStr Founder and CEO Jason Lemkin as Ryan reflects on the survey software maker's acquisition by SAP this year. The company was acquired this November in an $8B deal ahead of its planned IPO. This is SaaStr’s founder favorites series where you can hear some of the best of the best of SaaStr Annual’s Speakers. Missed the session? Here’s what Jason and Ryan talk about: Why did Qualtrics turn down a $500M acquisition offer in 2012? What did Qualtrics’ path to fundraising look like? How to build lifelong customers Capital efficiency (and dilution) If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin SaaStr This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Erica Schultz is Chief Revenue Officer @ New Relic, the company that gives you the real time insights your software driven business needs to innovate faster. Prior to their IPO, New Relic raised over $214m in funding from some of the best in the business including Benchmark, Insight Venture Partners and Blackrock, to name a few. As for Erica, under her CRO role, she leads all go-to-market functions including Marketing, Sales, Operations, Customer Success, Services, and Support. Prior to New Relic, Erica served as Executive Vice President of Global Sales and Customer Success at LivePerson and before that, Erica had a 16-year tenure with Oracle Corporation, where she founded and led numerous teams within the sales organization, including pioneering the company’s cloud business, and leading teams for North American and Latin American markets. In Today’s Episode We Discuss: How Erica made her way into the world of SaaS and came to be Chief Revenue Officer @ New Relic? What were some of her biggest takeaways from her incredible 16 year journey with Oracle? Why does Erica believe that enterprise is a “company sport”? Why does each department need to re-platform when making the move to enterprise? How can founders know when is the right time to make the move from SMB to enterprise? Where does Erica often see founders make mistakes with this scaling? How does the move to enterprise fundamentally impact the sales team? How does the structure of the sales team change with the move? How does the role of marketing change with the move to enterprise? How does this move impact the relationship between sales and marketing? How should compensation plans be altered with the move? With the scaling of departments and teams, what has Erica seen work really well when it comes to making cross-functional teams communicate really well? What are the inflection points where Erica often see communication or process begin to breakdown? How does Erica ensure the team are still in the trenches with the clients despite the scaling? From Erica’s experience, how do the very best sales reps build relationships with their prospects? Where do many go wrong? How much time does Erica believe reps should be given when it comes to translating relationships to dollars? What is the right way to think about payback period today? Erica’s 60 Second SaaStr: What does Erica know now that he wishes he had known at the beginning? The optimal relationship between CRO and CEO? The hardest element of being CRO @ New Relic? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Tom Tunguz is General Partner @ Redpoint Ventures, the venture fund with a portfolio including the likes of Stripe, Netflix, Zuora, Hashicorp and Juniper Networks just to name a few. As for Tom, he joined Redpoint in 2008 and has since led investments in Kustomer, Looker, Expensify and Gremlin all prior guests on the show I hasten to add. He is also the co-author of Winning with Data: exploring the cultural changes big data brings to business. Tom has also been named on the Forbes Midas Brink list. Before joining Redpoint, Tomasz was the product manager for Google’s AdSense social-media products and AdSense internationalization. In Today’s Episode We Discuss: How Tom made his way from creating software with his father in Brazil to being GP and forefront figure in the SaaS investment community as a GP at Redpoint today? Annual contracts: To what extent do annual contracts dominate today? How does this differ when comparing enterprise to SMB? Why does Tom think in the early days one should be wary of signing too many multi-year contracts? What are the dangers there? How does Tom think about calculating churn when it comes to multi-year contracts? What were the findings on what good looks like when it comes to logo retention? How does this differ when comparing SMB to enterprise? What were the commonalities of leading indicators of churn? Is it fair to always surmise that when serving SMB one will always have a higher rate of churn? What is the right way to conduct a churn analysis? Assisted vs unassisted: What does Tom believe are the leading benchmarks for both? How does this differ when comparing SMB to enterprise? How does the impact of a salesperson change the conversion rate? What time frame from SAL to closed lead suggests product market fit? What one question must all founders be asking in the sales process? How does Tom think about constructing comp plans the right way today? How should comp plans differ when comparing AEs to customer success? Where should the responsibility for upsell lie, customer success or sales? Should sales commission be paid on renewals? Tom’s 60 Second SaaStr: What does Tom know now that he wishes he had known at the beginning? What is Tom’s favourite book and why? What is Tom’s most recent investment and why did he say yes? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Tom Tunguz This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Nick Mehta is the CEO @ Gainsight, the #1 customer success platform for corporate services, turning your customers into your best growth engine. To date Gainsight have raised over $156m from some of the world’s best VCs in the form of Lightspeed, Bessemer, Insight Venture Partners, Battery Ventures and Salesforce Ventures. As for Nick, prior to Gainsight he was the CEO @ LiveOffice where he grew cloud archiving ARR from $2m in 2008 to $25m in 2011 and drove and negotiated the acquisition by Symantec for $115m in cash. Before LiveOffice Nick was Senior Director of Product Management @ Symantec where he led $378 MM market-leading email archiving / security businesses managing over 180 people across 3 continents. I do also have to say a huge thank you to both Byron Deeter and Jason Lemkin for the intro to Nick over two years ago. In Today’s Episode We Discuss: How Nick made his way into the world of SaaS and came to lead the charge in the category creation of customer success as CEO with Gainsight? What were some of his big lessons from being CEO at 2 companies during 2 macro market crashes? What does Nick mean when he says, “customer success will fail if it is just a role and not a strategy?” What can the leader and CEO do to imbue this company wide approach to customer success? What tangible actions are on offer? What works? Where do many make mistakes? Nick has previously said, “burying customer success undel sales does not work”. Why does this have such a high rate of failure? What should the optimal sales to customer success relationship look like? What does Nick mean when he says, “product is to customer success what marketing is to sales”. How should product and customer success work together? Why does Nick believe the mythology of the “A player” when business building is fundamentally dangerous? What can leaders and CEOs proactively do to ensure a diverse and differentiated talent pipeline? What question does Nick find most revealing in terms of one’s character and potential? Where do many go wrong in building and scaling their teams in SaaS? Why does Nick push back against the “hire fast and fire fast” thesis? What are the negative consequences of it? Why is it short-sighted and premature in many cases? What does Nick suggest for individuals struggling to find their optimal role within an organisation? How much time does one give someone struggling to find their role? Nick’s 60 Second SaaStr: Who must fundamentally own the renewal, sales or customer success? What Nick know now that he wishes he had known at the beginning? What would Nick most like to change in the world of SaaS? Most surprising action that has moved the needle for a company in terms of retention? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Nick Mehta This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

In Today’s Episode We Discuss: David Skok: General Partner @ Matrix Partners: Why does David believe that all good products have at least one variable pricing axis? How can founders determine which variable they should choose for their product? What are the pros and cons? Chetan Puttagunta: General Partner @ Benchmark: Why does Chetan believe we have seen a strong decline in the per seat pricing model? What are the major drawbacks of it? What are we seeing replace it? What has Chetan seen work well amongst his portfolio? Mark Suster: General Partner @ Upfront Ventures: What were Mark’s two biggest lessons on pricing from seeing the hyper-growth of Salesforce first hand? WHat does Mark advise founders when it comes to price anchoring and discounting? How does Mark view the sale of professional services with this in mind? Amanda Kleha: Chief Customer Officer @ Figma: What were Amanda’s biggest learnings from running the Zendesk pricing playbook? What does Amanda mean when she says that successful pricing is broke up into 3 separate product features? Brad Birnbaum: Founder & CEO @ Kustomer:Why does Brad push back on the common suggestion of a “no man’s land in SaaS pricing”? Why is innovation in pricing actually detrimental to sales in most cases? Guy Podjarney, Founder & CEO @ Snyk: How does Guy think about having a large enough base to test pricing strategies? How does Guy think about the balance between freemium and paid? Does one have to come first? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Bridget Gleason is VP of Sales @ Logz.io, the startup that uses predictive analytics and machine learning to provide monitoring, troubleshooting and security. To date, Logz have raised over $45m in funding from the likes of Openview, 83North and Vintage just to name a few. As for Bridget, she has the most incredible track record. Before Logz, Bridget was VP of Corporate Sales @ Sumo Logic where she drove ARR up by a record 237%. Prior to SumoLogic, Bridget was VP of Sales @ YesWare where she increased MRR per rep by 450%. Finally before YesWare, she was VP of Sales @ Engine Yard, where she tripled monthly recurring revenue, over course of 3+ year tenure, in 3 key leadership roles. In Today’s Episode We Discuss: How Bridget made her way into the world of sales and became the sales leader she is today, having started in the world of marketing? Having led and scaled numerous sales teams, does Bridget agree the best sales reps are outgoing and extroverted? How does the successful profile of a sales rep depend on (1) whether you are selling to SMB or enterprise? (2) The stage of the company? How can one stress test the character type of the candidate pre-hire in the interview stage? Does Bridget believe that sales reps really are as coin operated as many suggest? Why is that potentially an unfair position to take? How does Bridget think about structuring the right comp plans for her team? What other methods of incentivisation does Bridget believe works equally as efficiently? Does Bridget believe that you should pay sales rep commissions on services revenue? Should one pay the same or lower commissions on renewals? Should multi-year deals be paid upfront? How does one structure commissions for the sales team with that in mind? When does Bridget believe is the right time to hire (1) your first sales reps? (2) Your first VP of Sales? Why does Bridget believe that 70% of VP of Sales positions do not work out in the first 9 months? What can founders do to increase the likelihood of success within their VP of Sales role? Where do many go wrong? Bridget’s 60 Second SaaStr: What does Bridget know now that she wishes she had known when she started in SaaS? SDR’s are the most important function in the sales process, agree or not and why? Sales training, what works? What does not? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Bridget Gleason This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Amanda Kleha is the Chief Customer Officer @ Figma, the startup that allows you to turn ideas into products faster through design, prototyping and feedback gathering, all in one place. To date, Figma have raised over $42m in VC funding from some of the best in the business including Index Ventures, Kleiner Perkins, Greylock Partners and former guests on 20VC, Daniel Gross and Adam Nash. As for Amanda, prior to Figma, she held numerous roles at Zendesk including SVP of Marketing and Sales Strategy. Amanda joined Zendesk as the first marketing hire and over the next 7 years Zendesk grew to over 2,000 employees. Before Zendesk, Amanda worked on the marketing team for Google’s Enterprise SaaS businesses. If that was not enough Amanda is also an advisor at Airtable and Smartling. In Today’s Episode We Discuss: How Amanda made her way into the world of SaaS and came to join Zendesk as their first marketing hire seeing the company scale to over 2,000 over the next 7 years? What were some of Amanda’s biggest learnings from seeing Zendesk scale from 12 to 2,000? How does one determine those that can vs cannot grow with the business? What is the sign a stretch VP is a stretch too far? How does Amanda balance between a culture of risk taking but also not accepting failure to easily? How does Amanda like to run the interview process? Why does Amanda like to not show emotion when interviewing a candidate? What are the benefits of this for the brand of your company? What single question does Amanda find most revealing in showing the abilities and character of a candidate in an interview? What does Amanda mean when she says “pricing is made up of 3 components”? Where does Amanda believe most people go wrong with pricing? Is there such thing as no man’s land in SaaS pricing? How does Amanda think the go-to-market has to change with every stage of development? What are the challenges with this? How does the structure of decision-making change with scale? What are the inflection points? When does both decision-making and communication tend to break down? What can be done to ensure seamless cross-functional communication across the org? Where do most people fail here? Amanda’s 60 Second SaaStr: What does Amanda know now that she wishes she had known when she started in SaaS? Is there such thing as no man’s land in SaaS pricing? How to ensure customer support is strategic and not just reactionary? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Amanda Kleha This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Anne Raimondi has more than 20 years experience driving growth at startups and building them into nationally recognized brands. She has served as a leader and executive for technology innovators including Zendesk, Survey Monkey, Blue Nile, and eBay. Anne is also a Lecturer in Management at Stanford Graduate School of Business, teaching two popular courses, “Startup Garage” and “POWer: Building the Entrepreneurial Mindset.” She currently serves on the board of directors for SendGrid (NYSE: SEND) and MyHealthTeams. If that was not enough, Anne is also an active angel investor with an incredible portfolio including the likes of Canva, ipsy, and Minted just to name a few. In Today’s Episode We Discuss: How Anne made her way into the world of startups with Zendesk? How did seeing the hyperscaling of Zendesk impact Anne’s operational approach and mindset? Does Anne agree that certain individuals are destined for certain stages of company development? What are the leading indicators that one can or cannot scale? What are the inflection points in company growth where process tend to break? What can managers do to provide security in these times of change? Why does Anne believe that everyone should be a product person in SaaS? What are the inherent benefits of this product centricity? How does the element of product centricity change when catering to 2 customers, CIO and consumer? How does Anne advise on this issue of agency? How does Anne approach optimising internal decision-making processes? Where do many leadership teams make mistakes here? What is the right way for leadership teams to communicate their decisions to the wider team? How does Anne approach ensuring cross-functional communication at scale? How has Anne seen her style of board membership change over the last 8 years? What has been an inflection point that has changed the way she thinks about what it takes to be a great board member? Who has been the best board member Anne has worked with? What made them so special? Anne’s 60 Second SaaStr: What does Anne know now that she wishes she had known at the beginning? The right way for founders to view competition? What would Anne most like to change in the world of SaaS today? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Anne Raimondi This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Jason VandeBoom is the Founder and CEO of ActiveCampaign, a sales and marketing automation platform that enables small businesses around the world to meaningfully connect and engage with their customers. Jason founded the company in 2003 and under Jason's leadership, ActiveCampaign has flourished from a successful but small company and then in 2013, they transition to SaaS, since they have grown to more than $50 million in ARR in less than five years, while still maintaining profitability and its culture. They have also only raised a single $20m PE round to accelerate their growth, making them a market leader in terms of funds raised/ARR generated. In Today’s Episode We Discuss: How Jason made his way into the world of SaaS and came to found ActiveCampaign? Why is Jason so bullish that “SMB first, works”? What are the inherent benefits from starting at SMB? How does it affect product feedback? How does it affect how you build and scale your team? How does one start to layer in market and enterprise over time? Why does it give you additional leverage? What does Jason think is the right way to scale your sales team> Why does one not need funding to scale sales teams? When does Jason believe is the right time to hire your first VP of Sales? What were the biggest mistakes that Jason made in the scaling of his sales team? Why should hire 3 reps to start at one time? How does Jason view the current fundraising environment? Why does Jason believe that “no one cares if you get funding”? Why does Jason believe there is a fear around needing fast growth? Who is to blame for this? How should founders in the messy middle feel when seeing large fundraises in the media? Why does Jason believe that all leaders need to be consuming all feedback? How does Jason consume feedback on a daily basis? What metrics and elements does he look for in this assessment? How has Jason’s role changed over the 16-year CEOship? Does it get easier over time in Jason’s mind? What has been the biggest challenge? Jason’s 60 Second SaaStr: What does Jason know now that he wishes he had known at the beginning? No man’s land of SaaS pricing, exist or a myth? Multi-year deals, all they are cracked up to be or overrated? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Jason VandeBoom This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Ryan Barretto is the SVP of Global Sales at Sprout Social, a leading provider of social media engagement, advocacy and analytics solutions for business. To date they have raised over $111m in funding from the likes of NEA, Goldman Sachs and their very recently announced $40m Series D led by Future Fund. At Sprout Social Ryan oversees both the Sales and Customer Success organizations. Prior to Sprout, he was the VP of Global Sales at Pardot–a Salesforce company. At Pardot, Ryan's team tripled revenue growth in two years, making Pardot one of Salesforce's fastest growing businesses and during his 10 year tenure at Salesforce he saw the company grow from $180m to $7.5Bn. In Today’s Episode We Discuss: How Ryan made his way into the world of SaaS with Salesforce over 13 years ago? What were some of Ryan’s biggest takeaways from seeing Salesforce scale from $180m to $7.5Bn? Why does Ryan think that it is lazy to believe that you have to pick a market and you can’t have them all? How can one approach the element of very different messaging being required for SMB vs enterprise? How can one do both? How does that change the structure of the team? How can one build a product with the simplicity of SMB and functionality of enterprise? When it comes to winning the market, what does Ryan mean when he says, “boring is better than sexy”? What are the 4 elements all founders must consider when pricing their SaaS product? Where does Ryan see many go wrong with pricing? When serving SMB, how can one provide enterprise quality customer support? How does Ryan feel about customisation? What number justifies it? Why does Ryan believe that being good at sales won’t make you a great sales leader? What is needed to make the transition? What can sales reps do to learn and bridge that gap? What has worked for Ryan in the past? Where has Ryan seen many go wrong here? What 3 elements does Ryan look for in al additions to the team? What is the number 1 issue that is preventing people building truly diverse teams? How can we change our job descriptions to make the more inclusive? How can we expand our candidate pool to include more diverse people than usual? What can leaders do to build environments of inclusion where people can really bring their full selves to work? Ryan’s 60 Second SaaStr: What does Ryan know now that he wishes he had known at the beginning? Sales rep productivity, what is good to Ryan? What motto or quote does Ryan frequently revert back to? Why? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Ryan Barretto This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Guy Podjarny is the Founder & CEO @ Snyk, the developer-first solution that automates finding and fixing vulnerabilities in your dependencies. To date, Guy has raised over $32m in VC funding from Snyk from some of the great of venture including Accel, GV, our friends at Boldstart and Canaan Partners, just to name a few. As for Guy, prior to Snyk, he was the CTO of Akamai’s Web Performance Business following their acquisition of his startup, Blaze.io. Before founding Blaze, Guy built Web Application Security products, including the first Web App Firewall (AppShield), Dynamic Application Security Testing tool (AppScan) and Static Application Security Testing tool (AppScan Dev Edition). Fun fact on Guy, he is the holder of 18 patents related to security and performance. In Today’s Episode We Discuss: How Guy made his way into the world of SaaS and came to found one of the hottest open source companies of our day in the form of Snyk? How does Guy navigate between the difficult balance of going wide on market and shallow on product or narrow in market and deep in product? What is the decision-making process? What does Guy advise founders on feature prioritisation in the early days? Does Guy agree if you are not embarrassed by V1, you have shipped too late? How does support provide a feedback loop on what to build next? Why does Guy believe that, “successful freemium requires giving away your secret sauce”? How can one give away enough secret sauce in freemium without giving away too much people don’t buy? How does freemium fundamentally alter your relationship to revenue? Where does Guy see many going wrong when pursuing the freemium model? How does Guy think about the problem of agency with developers using the product but having to sell to CIOs? What 2 things can be done to make this sell easier? What does Guy believe is the right framework to think about pricing through? Why is transparency in enterprise pricing not always optimal? What does Guy believe is required to have strong and seamless communication across functions and locations? How has Guy seen this change over time and with increased locations? Where does Guy see many going wrong when trying to scale team across location? Guy’s 60 Second SaaStr: How does Guy know when is the right time to hire your first sales person? How did Guy learn to let go and trust his team? What does Guy know now that he wishes he had known at the beginning? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Guy Podjarny This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Claire Hughes Johnson, COO @ Stripe the new standard in online payments that handles billions of dollars of business every year for forward thinking businesses around the world. To date, Stripe has raised over $680m in funding from some of the very best in the business including Sequoia, Founders Fund, General Catalyst, Thrive, CapitalG, Kleiner Perkins and Tiger Global. As for Claire, prior to Stripe she spent over 10 years at Google in a range of different roles from VP of Google's self-driving car division to VP of Global Online Sales to VP of Google Offers. At Stripe, Claire has helped take Stripe global in February 2016 with the launch of Atlas, a toolkit that enables any business, anywhere in the world, to incorporate in the United States. If that was not enough, Claire is also a Board Member @ Hallmark Cards. In Today’s Episode We Discuss: How Claire made her way into the world of SaaS with Stripe following her leading of Google’s self-driving car division? What does Claire mean when she discusses “founding documents”? What is the right way to go about creating them? What element do they need to contain? How can one optimise internal decision-making process with these documents? What question must one always try and ask when making big decisions? How does Claire define a truly special COO? What does that truly great look like? When is the right time for founders to hire that COO? Where do the majority of people go wrong in their assessment of when and what they need in a COO? What is the optimal relationship one can have between CEO and COO? How does Claire think about what Stripe have done right to hire so effectively at scale? What does it take in terms of benchmarks and standards to do so? What does Claire mean when she says you have to step function up your capabilities with scale? What are the core challenges in hiring at scale? Claire’s 60 Second SaaStr: What would Claire say are her biggest strengths and weaknesses? What does Claire know now that she wishes she had known at the beginning? A moment in Claire’s life that has served as an inflection point and changed the way she thinks? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Claire Hughes Johnson This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Krish Subramanian is the Founder & CEO @ Chargebee, the startup that lets you go beyond billing, payments and recurring invoices — to delivering subscription experiences that "wow". To date, Chargebee have “wowed” some of the world’s leading VCs to the tune of $24m including the likes of Insight Venture Partners, Tiger Global and Accel Partners. As for Krish, under Krish’s leadership the team has grown to over 200 people and over 5,000 clients making it one of the next generation in truly global SaaS businesses started in India. In Today’s Episode We Discuss: How Krish made his way into the world of SaaS and came to found one of India fastest growing SaaS companies in Chargebee? Why does Krish believe that every SaaS company should bootstrap at some stage? What are the inherent benefits to these capital constraints? What are the drawbacks to not having the capital reserves? What was the inflection point for Krish in realising he wanted to go big and raise from Insight? Why does Krish believe that it is wrong to think of the word “service” as being negative in SaaS? What are some of the foundational benefits to building out a strong services division? How does Krish think about what makes for good margins in services businesses? How can one prevent themselves from being reliant on service revenue? Why does Krish believe that transparency is not always good when it comes to SaaS pricing? What are the cons of transparent pricing? Why does Krish believe if you are going to try freemium, it has to be from the beginning? How does Krish think about reinventing the wheel vs copying when it comes to pricing? How does Krish think about installing usage based pricing without disincentivizing usage? How can one do it? Krish’s 60 Second SaaStr: What does Krish know now that he wishes he had known at the beginning? What moment in Krish’s life has served as an inflection point and changed the way he thinks? What does Krish believe that most around him disbelieve? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Krish Subramanian This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Karen Peacock is the COO @ Intercom, the company that provides a new and better way to acquire, engage and retain customers. To date, Intercom have raised over $240m in VC funding from some of the very best in VC including GV, Kleiner Perkins, Bessemer, ICONIQ and then individuals such as Mark Zuckerberg, John Collison, Biz Stone and Andy McLoughlin. As for Karen, prior to Intercom, she spent an incredible 17 years at Intuit leading all of Intuit’s small business products and services worldwide, a $2.2B business including QuickBooks, Accounting, Payments, and Payroll. As part of that, Karen managed a team of 500 and helped build one of the world’s largest SaaS businesses. In Today’s Episode We Discuss: How Karen made her way into the world of SaaS with Intuit and how that led to becoming COO @ Intercom today? What were Karen’s biggest takeaways from her time at Intuit? What does Karen mean when she says “watch what customers do, not what they say”? How does Karen think about the difference between being customer driven vs customer informed? Why is it important to fall in love with the problem and not the solution as an entrepreneur? Karen has grown Intercom from 350 to 600 in 18 months, what would Karen’s biggest advice and learnings be when it comes to team assembly and hiring the best? What can one do to stress test the fit of the candidate pre-hire? What does Karen always find to be the most revealing questions to ask? When does Karen believe is the right time to hire a COO? How does one know when they have the right COO fit? What are some best practices for onboarding a new COO? What is the optimal relationship between CEO and COO? Karen has seen incredible scaling first hand both with Intercom and Intuit, what would some of her biggest takeaways and advice be on scaling? Where does Karen see many make mistakes in the scaling phases? What does Karen mean when she speaks about “the most important metric that you probably aren’t tracking?” Karen’s 60 Second SaaStr: What does Karen know now that she wishes she had known at the beginning? What motto or quote does Karen frequently revert back to? What is the most challenging element in Karen’s role today? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Karen Peacock This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Hannah Willson is the VP of Sales @ Rainforest QA, the on-demand QA solution that allows companies to discover problems that affect the customer experience before the code hits production. To date, Rainforest have raised over $40m in funding from some of the very best in SaaS including the legendary Byron Deeter @ Bessemer, Jason Lemkin @ SaaStr, Marc Benioff himself, Andreesen Horowitz and YC. As for Hannah, she has over 10 years of experience leading sales and customer teams at both startups and publicly traded companies including seeing the first hand hyper-growth of Zenefits in their heyday and being VP of BD, Sales and Customer Renewals for the western half of the US at HelloWallet, prior to their acquisition by Morningstar. In Today’s Episode We Discuss: How Hannah made her way into the world of SaaS and enterprise sales, came to join Zenefits in their heyday and how that led to her move to VP of Sales @ Rainforest? How does Hannah think about time allocation and prioritisation of time across leads and the sales pipeline? WHat can AEs do in terms of optimising their win rate of opportunities? How important a role should discounting play in winning potential leads? Does Hannah optimise for quality or quantity of logos in the early days? What does Hannah mean when she says the secret to success is “the calls between the calls”? How do these vary both in content and tone to traditional sales calls? Why must AEs be willing to open up and be vulnerable with leads? What can managers do to engender this? What is the optimal relationship for AEs and product team? What does Hannah believe is the right mechanism for feedback delivery? What has worked well for her in the past? Where does Hannah see many today going wrong? What guidelines need to be put in place to ensure this candid and transparent feedback is effective? Hannah’s 60 Second SaaStr: What does Hannah know now that she wishes she had known at the beginning? What does Hannah believe embodies good sales rep productivity? What is Hannah’s fave SaaS reading material? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Brad Birnbaum is the Founder & CEO @ Kustomer, the first intelligent platform for customer experience that enables you to know everything about every customer. To date Brad has raised over $38m in funding for Kustomer from some of the very best in the SaaS business including Tomasz Tunguz @ Redpoint, Ed Sim @ Boldstart, Canaan Partners, Box Group and Social Leverage just to name a few. Previously he was the Co-founder of Assistly, which was acquired by Salesforce and became Desk.com. Prior to that, he was CTO for Talisma and Co‑founder & CTO of eShare Technologies. In addition, Brad was also the CTO @ Sean parker’s Airtime and VP of Engineering with Salesforce. In Today’s Episode We Discuss: How Brad made his way into the world of customer experience and SaaS over 20 years ago? This is Brad’s 4th time at the roadshow, what does Brad believe are the core benefits of repeat entrepreneurship? How did his prior experience change his operating mentality with Kustomer? What has he done differently this time? What worked and he has kept the same? Brad has made the transition from CTO to CEO, how did he find this transition? What were some of the most challenging elements? What have been some of the biggest surprises? What advice would Brad have for other CTOs who have made or are thinking about making the transition? Brad initially served SMBs with Kustomer but now primarily focuses on mid-level, what would Brad’s biggest advice be when it comes to finding the right go-to-market strategy for you? How did their transition alter their approach to pricing, product, messaging and distribution? Where does Brad see many people go wrong on go-to-market? Brad’s 60 Second SaaStr: What does Brad know now that he wishes he had known at the beginning? When is the right time to pour fuel on the company fire? What would Brad most like to change in the world of SaaS? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Brad Birnbaum This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Jon Stein is the Founder & CEO @ Betterment, the online financial advisor built for people who refuse to settle for average investing. To date, Jon has raised $275m in VC funding with Betterment from the likes of Bessemer Ventures Partners, Menlo Ventures, Kinnevik and Francisco Partners, just to name a few. Prior to founding Betterment, Jon spent 4 years as a consultant at First Manhattan Consulting Group where he really honed his experience in working with banks and brokers including revitalizing a bank in Australia with the launch of a best-in-market auto-finance offering, resulting in 50% lift to revenue. As a result of his phenomenal success with Betterment Jon has won many awards including Fortune’s 40 Under 40. In Today’s Episode We Discuss: How Jon made his way into the world of startups and came to found democratize the world of investing with Betterment? When does Jon believe is that critical moment when the founding team must hire their first employee? What is the right strategy to build the candidate pipe for hiring those first employees? Where does Jon see many go wrong here? What 1-2 questions does Jon always find the most enlightening to ask in the interview? Once hired, what have been some of Jon’s biggest lessons in terms of optimising the onboarding experience and the first 60 days? How has their process changed over time? How does Jon determine when a stretch candidate is a stretch too far? If so, what does Jon believe is the right way to let go of an individual? What does Jon believe to be the 3 core roles of the CEO in any company today? From those, what has Jon found most challenging? What did he do to level up and overcome the challenges? How does Jon approach transparency with the team in delicate cases like fundraising and acquisition etc? With the team and product in place, scale can occur, what are the 2-3 things that all companies need to focus on when product market fit has been achieved? How does Jon determine when is the right time to really put the pedal to the metal and scale? Jon’s 60 Second SaaStr: Jon’s favourite book and why? What does on know now that he wishes he had known at the beginning? What is Jon’s biggest strength and weakness? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Jon Stein This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Maria Pergolino is the CMO @ Anaplan, the company that allows you to accelerate decision-making with effective planning. To date, Anaplan have raised over $299m in funding from the likes of Meritech, Salesforce Ventures, Shasta, DFJ Growth and more incredible names. As for Maria, prior to Anaplan, Maria was Senior Vice President of Global Marketing and Sales Development at Apttus, where she directed go-to-market strategy, sales development, customer advocacy, demand generation, strategic events and communications initiatives. She also has held leadership positions at Marketo, Shunra Software (acquired by Hewlett-Packard), and Chubb Ltd. It’s also important to note, Maria is renowned for building world-class teams that drive growth, product differentiation, and category development. In Today’s Episode We Discuss: How Maria made her way into the world of B2B marketing? What were her biggest lessons from the days of Marketo? How does Maria balance between instinct driven decision making vs data-driven in B2B marketing? Is there anything wrong with instinct driven? How can marketers confidently back up their thesis with substantive proof? How does one successfully sell that to leadership? Maria is famous for rallying teams around her ideas, what has Maria found to be core to the success in gaining this collective approval and excitement? What is the right way to approach the marketing portfolio of strategies as a whole? What channel or segment is Maria currently most excited for? How does maria evaluate the current event landscape in terms of effectiveness? Are we in a B2B event bubble? How can companies determine whether this is the right strategy for them? Would Maria agree with Joe Chernov, “to do events, you have to have an appetite for losing money? What does Maria and her team do to get the most out of events? What does the term “marketing playbook” really mean to Maria? What does Maria mean when she suggests that marketers can let their own playbook get in the way? Why does maria think it is absurd for there to be misalignment from sales and marketing? Maria’s 60 Second SaaStr: What does Maria know now that he wishes he had known at the beginning? Who does Maria believe is killing it in B2B marketing today? Advice commonly stated in SaaS that Maria disagrees with? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Maria Pergolino This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Cristina Cordova leads the Payments Partnerships and Platform Partnerships teams at Stripe, the new standard in online payments that handles billions of dollars of business every year for forward thinking businesses around the world. To date, Stripe has raised over $680m in funding from some of the very best in the business including Sequoia, Founders Fund, General Catalyst, Thrive, CapitalG, Kleiner Perkins and Tiger Global. As for Cristina, at Stripe she manages partnerships with some of the biggest global players including Apple Pay, Google Pay, WeChat Pay and more and has also held roles such as Head of Diversity and Inclusion and Manager of Partner Engineering. Prior to Stripe, Cristina was Head of Business Development @ Pulse (acq by LinkedIn) and was in the marketing team at Tapulous (acq by Disney). In Today’s Episode We Discuss: How Cristina made her way into the world of SaaS and came to be Head of Partnerships at one of the fastest growing startups in the world, Stripe? Does Cristina agree with the common notion that certain people are destined for certain stages of a company’s life? How can one determine whether some has the ability to scale or not? What are the leading indicators? What have been some of Cristina’s biggest lessons in scaling from 28 at Stripe to 1,300? What does Cristina believe is the key to success when it comes to adapting to new roles? What worked? What did not work? Where does Cristina see many go wrong? How should employees think about title both when joining and when at a high growth company? What is the right way for them to think about and approach equity? What does Cristina believe is so special about partnerships with early stage startups? How can partnerships be fundamentally dangerous for early stage companies? How can startups determine when is the right time to engage with partners? What are the key questions and terms startups should focus on when partnering with incumbents? What makes Cristina lean in on a partnership for Stripe? What does Cristina believe is the right way to communicate this excitement and set expectations? For the larger player, what does the optimal agreement look like? What are the commonalities in the reasons that Cristina passes on potential partnerships? Cristina’s 60 Second SaaStr: What does Cristina know now that she wishes she had known at the beginning? Who is killing it in SaaS partnerships today? When is the right time to hire a Head of Partnerships? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Cristina Cordova This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Claire Hughes Johnson is the COO @ Stripe, the new standard in online payments that handles billions of dollars of business every year for forward-thinking businesses around the world. To date, Stripe has raised over $680m in funding from some of the very best in the business including Sequoia, Founders Fund, General Catalyst, Thrive, CapitalG, Kleiner Perkins and Tiger Global. As for Claire, prior to Stripe she spent over 10 years at Google in a range of different roles from VP of Google's self-driving car division to VP of Global Online Sales to VP of Google Offers. At Stripe, Claire has helped take Stripe global in February 2016 with the launch of Atlas, a toolkit that enables any business, anywhere in the world, to incorporate in the United States. If that was not enough, Claire is also a Board Member @ Hallmark Cards. In Today’s Episode We Discuss: How Claire made her way into the world of SaaS with Stripe following her leading of Google’s self-driving car division? What does Claire mean when she discusses “founding documents”? What is the right way to go about creating them? What element do they need to contain? How can one optimise internal decision-making process with these documents? What question must one always try and ask when making big decisions? How does Claire define a truly special COO? What does that truly great look like? When is the right time for founders to hire that COO? Where do the majority of people go wrong in their assessment of when and what they need in a COO? What is the optimal relationship one can have between CEO and COO? How does Claire think about what Stripe have done right to hire so effectively at scale? What does it take in terms of benchmarks and standards to do so? What does Claire mean when she says you have to step function up your capabilities with scale? What are the core challenges in hiring at scale? Claire’s 60 Second SaaStr: What would Claire say are her biggest strengths and weaknesses? What does Claire know now that she wishes she had known at the beginning? A moment in Claire’s life that has served as an inflection point and changed the way she thinks? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Claire Hughes Johnson This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Dan Reich is the Founder & CEO @ Troops.ai, the startup that is the ultimate slackbot for sales teams. To date, Dan has raised over $17m in VC funding with Troops from many friends of the show including Felicis Ventures, Founder Collective, First Round, Nextview, Susa Ventures and even Slack. As for Dan, he is also the Co-Founder and President of TULA, a private equity backed health and beauty business that has developed the world's first line of probiotic skincare products. Before that, Dan was a Co-Founder of Spinback (acquired by Buddy Media in May 2011, then acquired by Salesforce in June 2012). In Today’s Episode We Discuss: How Dan made his way into the world of SaaS with the founding of Spinback? How that led to his founding of the ultimate slackbot for sales teams in Troops? How the experience with Spinback affected his operating mindset with Troops today? Why does Dan believe that the current modelling of org charts is fundamentally upside down? How does Dan think about when is the right time to insert the first level of managers? What should one look for in those managers? Does Dan believe you have to hire “logo players” from big firms at some point in the journey? Why does Dan believe that your customer success has to be obsessed with asking why? Taking a step back, how does Dan think about when the right time is to hire your first CS rep? How has Dan seen the best companies do post mortem analysis on churn? What can be done to ensure seamless communications between product and customer success teams? Dan has a knack for knowing where the puck is going with large enterprises before anyone else. How? What does this ideation process look like? Once the idea has been created, what does Dan believe is crucial to the success of partnering with the behemoths of Salesforce and Slack? How can startups navigate the internal politics of these mega enterprises? How can they use this exercise to not only understand the politics themselves but also build credibility and trust with the organisations once inside? Where does Dan see most founders going wrong both in introductions to enterprise and then building trust once inside? Dan’s 60 Second SaaStr: What does Dan know now that he wishes he had known at the beginning? What is Dan’s favourite story of hustle? Why that one? Who does Dan believe is killing it in the world of SaaS today? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Dan Reich This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Steve Newman is the Founder & CEO @ Scalyr, the startup that helps your devops team solve more problems in less time with log monitoring and analysis in seconds. Steve has raised over $27.5m in funding with Scalyr from many friends of the show including Susa Ventures, Bloomberg Beta, Shasta and GV. As for Steve, prior to Scalyr, he was the Founder of Writely which was acquired by Google to become the little known, Google Docs. Before that he founded 2 prior startups, Ann Arbour Softworks (acq by Ashton-Tate) and BitCraft (acquired by Macromedia). If that was not enough, Steve also sat on the Technical Advisory Board at Box for over 3 years. In Today’s Episode We Discuss: How Steve made his way into the world of startups and SaaS over 30 years ago? What is the founding story with Scalyr and what was that a-ha moment? Why does Steve believe that you should involve customers very early in the process of developing your narrative? Where does Steve see most startups go wrong when it comes to messaging? How does one structure the feedback mechanism? How does one determine between feedback you integrate and feedback you do not? Why does Steve believe that you should not focus too much on numbers in the early days? What makes them deceiving at this stage? If not numbers, what should early stage founders be focusing on and measuring? Why does Steve believe that ARR is not the leading metric? What metrics should early stage SaaS founders really be prioritising? How does Steve respond to PG’s “to scale, you have to do unscalable things”? What challenges and nuance does Steve present that founders must be wary of? How does Steve’s thinking here affect his view towards customisation? Why does manual input not put a cap on scalability? What are the parameters for manual involvement to be scalable? Steve’s 60 Second SaaStr: What does Steve know now that he wishes he had known at the beginning? Who does Steve believe is crushing it in the world of SaaS today? The hardest element about the move from tech co-founder to CEO? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Joe Chernov is the Chief Marketing Officer at Robin, the startup that simplifies scheduling, visibility and management of meeting rooms, desks and people in your workplace. To date, Robin have raised over £9m in funding from some of our dear friends in the form of BoldStart, Accomplice and FirstMark, just to name a few. As for Joe, prior to Robin he was the CMO @ Insight Squared where he led the transition from an email-driven leads model to an account-based marketing model that's tightly coupled with sales. Before InsightSquared, Joe was Head of Content Marketing at Hubspot where he increased blog traffic by more than 1M visits/month and increased leads by 40%. Finally, pre-Hubspot, Joe held VP of Marketing roles at Kinvey and Eloqua. In Today’s Episode We Discuss: How Joe made his way into the world of startups and SaaS marketing many years ago? What was Joe’s missed founding story and how does that affect his thinking today? Does Joe believe that ABM is a paradigm shift in the way we approach marketing or another word for high ACV target sales? How can founders determine whether they have the right business, pricing and hiring strategy that will align with an ABM strategy? Is it the right decision to focus squarely on ABM? How should it play into your overall marketing portfolio? Why does Joe believe we have seen a massive rise in SaaS conferences? How can a startup determine whether the conference strategy is the right strategy for them? Where does Joe see many startups going wrong when selecting this approach? Why does Joe believe you have to get comfortable with losing money in conferences? What are the determinants or leading indicators of a successful conference? What is the ideal composition in terms of attendance? Why does Joe believe that marketing should be held accountable to a number that is directly tied to revenue? Why does Joe believe that Head of Sales and Head of Marketing should not be separate functions? What is it that leads Joe’s thinking when saying, sales and marketing are overlapping functions? What are the commonalities of the truly special CMOs? When is the right time to really consider adding the CMO to your exec team? What is the ideal relationship between the CMO and the CEO? What is the one question that will largely determine the strength of a potential CMO? Joe’s 60 Second SaaStr: What does Joe know now that he wishes he had known at the beginning? Who does Joe believe is killing it in SaaS today and why? Advice Joe often hears in the world of SaaS that he actively disagrees with? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Joe Chernov This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Michael Katz is the Founder & CEO @ mParticle, the customer data platform that integrates all of your data and orchestrates it across channels, partners and systems. To date, Michael has raised over $75m in funding with mParticle from the likes of Social Capital, Greylock Partner, GV, Battery Ventures and more great names. Prior to founding mParticle, Mike was the Founder & CEO @ Interclick, where he organically grew revenue to over $140m in 5 years. The company went public in 2009 and was acquired by Yahoo in 2012 for $270m, a 50% premium on existing share price. If that was not enough, Michael is also a board member at Adaptly and Brightline. In Today’s Episode We Discuss: How did Michael make his way into the world of SaaS with the founding of Interclick? How did that translate to his founding and running of mParticle today? How does Michael think about building a company and a category at the same time? In terms of resource allocation, if one is required to invest heavily into brand, how can this be done with a seed round? What were the most challenging elements of category creation for Michael with mParticle? When it comes to selling to enterprise, how can startups look to meet and stand out in the sea of startups to the enterprise buyers of today? How can they look to build trust with those buyers? How much of a role do VCs provide in terms of providing legitimacy and validation to a startup? Before Michael has said ‘multi-year deals are not good’, why does he hold this belief contra to most in the ecosystem? In which cases do they work well and is there nuance? How does Michael think about the element of deferred revenue and it’s subsequent effect on potential acquirers? How does Michael think about pilot programs? If mainly selling to one market segment, should pilots within other segments be accepted? What conditions on signing must be set to ensure success on completion of pilot? How should pilot programs change and evolve over time with the company? Michael’s 60 Second SaaStr: What does Michael know now that he wishes he had known at the beginning? Who is crushing it in SaaS right now? Why? Pros and Cons of building SaaS startup in NYC? Motto or quote that Michael most frequently reverts to? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Michael Katz This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Kyle Porter is the Founder & CEO @ Salesloft, the leading sales engagement platform delivering a better sales experience. To date, Salesloft have raised over $75m in funding from some of the best in the business including Emergence, Insight Venture Partners, Techstars and even LinkedIn. As for Kyle, he has led the team from 4 employees in 2014 to over 320 today where they have also been awarded Atlanta’s No 1 best place to work. Prior to founding Salesloft, Kyle was the Founder @ B2B camp, a conference focused on B2B revenue generating professionals. Before that he was Vice President of Marketing @ NanoLumens. In Today’s Episode We Discuss: How Kyle made his way into the world of SaaS and came to found Salesloft? Kyle made the decision to pivot the product when it was at $7m in ARR, what was the thinking behind that? How does Kyle think about pivots more broadly? How does one know when it is truly not working? How long did it take Kyle to get the core Salesloft product to $1m in ARR? With the pivot, what were Kyle’s core learnings on migrating from a prior product and platform to a new one? What were his big lessons on seeing the change in buyer persona? What does Kyle mean when he says “selling is hard but buying is even harder”? Does Kyle agree with many CEO’s the most important role of the CEO is “management upscaling”? What elements does he find most challenging? What have been Kyle’s big lessons in the building out of his exec team? What is the fundamental element for a successful exec team to function? Salesloft is in an immensely competitive space, what would Kyle’s advice be in standing out in an intensely competitive space? Where do many go wrong? What are the pros and cons of being in Atlanta and not SF? What advice would Kyle give to founders operating their HQs external to the core hubs? Kyle’s 60 Second SaaStr Is it important to have early champions? How does one get them? How has having kids changed your perspective on work? Tell me a moment in your life that has served as an inflection point and changed the way you think? When I say success in SaaS who is the embodiment of this to you? What does Kyle know now that he wishes he had known at the beginning? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Kyle Porter This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Ed Sim is the Founder & General Partner @ Boldstart Ventures, one of the leading players in early stage SaaS investing. Their MO, to be a first check VC for enterprise founders and they have backed the likes of GoToMeeting (acq by Citrix), LivePerson (IPO, NASDAQ), Divide (acq by Google), Kustomer, Snyk and BigID just to name a few. Ed is also a cofounder of MState, a growth lab for enterprise blockchain in partnership with IBM. Ed is also a board director/observer of Kustomer, Hypr Biometric, Snyk, BigID, Fortress IQ, Wallaroo Labs and Manifold. If that wasn’t enough, Ed is also the writer behind BeyondVC, a must read blog in the world of SaaS. In Today’s Episode You Will Learn: How Ed made his way into the world of VC from one very meaningful high school lecture that changed his life and career path? What does Ed mean when he says “founders should not sell their product to enterprise in the early days”. Starting from the ground up, what can founders do to begin that relationship building process with enterprise buyers and CIOs? What can a startup do to establish that trust in the mind of large buyers? How much of a role does VC backing provide in comforting enterprise buyers? What would Ed advise founders contemplating the debate of going SMB up to enterprise or enterprise to SMB? What role should product play in this decision-making process? What are the leading indicators in testing the product that founders should observe for and guide their direction? Where does Ed most often see founders make mistakes here? How does Ed think about discounting? Would he agree with a previous guest that “discounting is now table stakes”? Rather than the financial element, what does Ed believe the founder should really be looking to get from the buyer in terms of commitment? How does Ed approach and assess pilots? To what extent should they be free or paid? What can be done to set the benchmarks for success and ensure closing? Ed’s 60 Second SaaStr What does Ed know now that he wishes he had known in the beginning? Quality or quantity of logos? What would Ed most like to change in the world of SaaS? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Ed Sim This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Craig Walker is the Founder & CEO @ Dialpad, the startup that provides a business phone system for the modern workplace. To date, Craig has raised over $120m in VC funding with Dialpad from some of the best in the business including Iconiq, Andreesen Horowitz, Google Ventures, Felicis and Bill Marris’s Section 32. Prior to Dialpad, Craig was an EiR @ Google Ventures and founded and product managed Google Voice. Before that Craig founded Grand Central Communications, a personal communications startup that was acquired by Google. Finally prior to that, Craig enjoyed roles in the world of VC as General Partner @ Sterling Payot Capital and Founder & Senior Director of Yahoo Voice. In Today’s Episode You Will Learn: How Craig made his way into the world of SaaS following time as both a GP in the world of venture and then as the creator of what would become Google Voice? Why does Craig think go-to-market is the most challenging element of being a CEO? How does Craig think about when is the right time to go large on go-to-market? Where does Craig believe most founders make mistakes here? How does Craig look to balance aggressive scaling of team with the maintaining of early company culture? What are the foundations to doing this successfully? How does Craig approach the element of hiring external talent vs promotion from within? How does Craig think about managing the internal discontent if hiring an external candidate? How does Craig assess the effectiveness of trials in attracting large enterprises? What are the parameters that must be set for a trial, before it is agreed? What must founders learn to say no to when it comes to trials? How does Craig approach discounting? Why does Craig argue if your client asks for aggressive discounts, you have not explained your core USPs successfully? Craig’s 60 Second SaaStr What does Craig knows now that he wishes he had known at the beginning? When I say success in SaaS, who does Craig first think to and why? Quality or quantity of logos and why? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Craig Walker This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Fouad ElNaggar is the Founder & CEO @ Sapho, the only employee experience portal designed for the digital workforce. To date, Ray has raised over $27m in funding with Sapho from some real favourites of ours including Ray @ Caffeinated, Felicis, Uncork, Bloomberg Beta, Clark Landry and Howard Lindzon @ Social Leverage, just to name a few. Prior to founding Sapho, Fouad was the Chief Strategy Officer at CBS Interactive overseeing strategy, operations, partnerships, and M&A. At CBSi, Fouad structured deals with partners such as Yahoo, IAC, and Twitch and acquired premium brands such as TV Guide and Giant Bomb. Prior to CBSi, Fouad was a VC at Redpoint Ventures overseeing the firm’s LA office and helping establish a dedicated fund in Brazil. Fouad has previously founded three venture-backed companies – Marketing Technology Solutions (acquired), Liquid Light (acquired), and Hark. In Today’s Episode You Will Learn: How Fouad made his way from the world of VC to the world of CBS and media to founding SaaS companies being a serial SaaS founder with his 4th company, Sapho? What does Fouad mean when he says the role of the CEO is to be an “inspirational a*****e”? Why is this role so crucial and how is it embodied both in the approach to inspiring a team and driving goals and decision-making? How does Fouad think about structuring decision-making internally? Where do so many go wrong in implementing a decision-making process? Why is Fouad a believer that “it is about coaching and promoting rather than signal hiring”? What does Fouad really interpret as signal hiring? When does signal hiring work well? How does Fouad determine when a stretch VP is a stretch too far? What are the leading indicators? Does Fouad agree with Mariam Naficy that rotation of function is key to internal upscaling? What does Fouad believe are the 2 fundamental benefits of “being old” in SaaS? How would Fouad respond to the suggestion that the rate of decay on experience has never been greater with Moore’s law effect on technology? Applied to hiring, how does Fouad think about the decision to hire a jack of all trades vs a specialist? When is the time to make the transition? Fouad’s 60 Second SaaStr What does Fouad know now that he wishes he had known at the beginning? A moment in Fouad’s business life that changed the way he thinks? What would Fouad most like to change in the world of SaaS today? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Fouad ElNaggar This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Christoph Janz is the Managing Partner @ Point Nine Capital, one of Europe’s leading early stage funds with a portfolio that includes the likes of ZenDesk, Algolia, Delivery Hero, Revolut, Contentful and many more incredible companies. Before that, he co-founded two Internet startups (DealPilot.com in 1997 and Pageflakes in 2005). In 2008 he became an angel investor and discovered Zendesk, Clio, FreeAgent – and his love for SaaS. Christoph is also the writer of the phenomenal blog, The Angel VC, a must read for me. In Today’s Episode You Will Learn: How Christoph made his way from serial founder to angel in ZenDesk to today, founding one of Europe’s most successful early stage funds in the form of Point Nine Capital? Product market fit is one of the most used words in the industry, so wtf really is product market fit? What does product market fit look like in terms of metrics across the core disciplines: MRR, churn and conversion from free to paid? What is the hailed question that all Series A and B investors want to know? What does it take to make the graduation from Seed to Series A today? In terms of scaling, why does pouring fuel on the marketing fire not always equal more leads? How does Christoph view the role of outbound? Why is it such high hanging fruit? What is core to executing outbound successfully? Point Nine did a comprehensive assessment of how founders view the fundraising process, what were the biggest elements founders dislike about the process? From now on, what is the thinking behind the strategy that Point Nine will always do their pro-rata in the Series A? How does this affect reserve allocation? Christoph’s 60 Second SaaStr What does Christoph know now that he wishes he had known in the beginning? What does it take for European founders to make it big in the US? Most common mistakes CEOs make in the scaling process? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Christoph Janz This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Tom Bogan is the CEO of Adaptive Insights, the company that proves a new generation of business planning software for finance and beyond. Prior to their reported $1.55Bn acquisition to WorkDay, Adaptive Insights raised over $175m in VC funding from the likes of Bessemer, Salesforce Ventures, Norwest Venture Partners and many more incredible investors. Prior to Adaptive Insights, Tom was a partner at Greylock Partners where he focused on enterprise software investments. He was also president and COO at Rational Software until its acquisition by IBM. Before Rational, Tom served as CEO at Avatar Technologies and Pacific Data. He began his career as a financial officer in both public and private companies, serving as CFO at SQA and Orange Nassau, Inc., as well as vice president of finance at SCA Services. In Today’s Episode You Will Learn: How Tom made his way into the world of SaaS, came to be a Partner with Greylock and then made the move back into operations with Adaptive Insights? Elad Gil has previously said the role of CEO is to “find product market fit, ensure the company does not run out of money and ensure the team does not implode”, how does Tom define his role as CEO of a $100m+ SaaS company? How does the role of CEo fundamentally change over time? What aspect of the role does Tom find most challenging? What core role of CEO is constant throughout the lifecycle of the company? From seeing many of the world’s best SaaS CEOs, what are the commonalities in how the very best CEOs hire the very best execs? How does Tom think about the debate of hiring externally or promoting from within? How does Tom look to reduce internal discontent when hiring externally rather than promoting? At $100m Jyoti Bansal said on the show, this stage is about “creating and sustaining operational efficiency”. What have been Tom’s biggest learnings on the creation and maintenance of operational efficiency? What has worked? What has not worked? How does Tom think about internal asset allocation? Why does Tom believe that ultimately, ARR growth is the metric to rule them all? How does Tom think about and prioritise the metric stack in SaaS? How does he approach payback period vs CAC/LTV? In terms of services components of businesses, does Tom believe these should be baked into the CAC? What should the financial targets be for these services businesses? Tom’s 60 Second SaaStr What does Tom know now that he wishes he had known at the beginning? Tom’s favourite business reading material and why? What would Tom most like to change in the world of SaaS today? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Jonah Goodhart is the CEO @ Moat, the SaaS analytics and intelligence company focused on transforming brand advertising online. Prior to their acquisition by Oracle for a reported $850m Moat raised over $67m in VC funding from the likes of Insight Venture Partners, Founders Fund, Mayfield, Founder Collective, SV Angel and more incredible names. Prior to founding Moat, Jonah was the founding investor and board member at Right Media, acquired by Yahoo for a reported $680m. Jonah was also the founding partner of WGI Group and co-founder of Billions.org. If all of that was not enough, Jonah is also an angel investor including the likes of adroll, Namely and fitmob all in his personal portfolio. In Today’s Episode You Will Learn: How Jonah made his way into SaaS with is founding investor role in Right Media? How did experiencing both bubbles change the way Jonah thinks about operations today? How does Jonah fundamentally define “North Star”? How plastic and flexible does Jonah believe a North Star should be? What was a time where Jonah’s decision was guided in a certain direction by his strong North Star? Why does Jonah believe that in B2B your roadmap is given to you by your customers? What can founders do to clearly and quickly determine what their customers want from their conversations with them? What questions are crucial to ask? What response suggests real intent to buy from them? How does one prevent this from falling into heavy customisation? How does Jonah approach the element of “brand” in the world of B2B today? What does Jonah believe is the secret to brand? How does this affect how Jonah both onboards, trains and engages with new and existing employees? Was brand core to Moat being able to sell to enterprise so successfully in the early days? Jonah’s 60 Second SaaStr What does Jonah know now that he wishes he had known at the beginning? Quality or quantity of logos in the early days? How important is it for SaaS founders to be involved in the process? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Jonah Goodhart This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Sam Blond is Chief Sales Officer @ Brex, the startup that provides corporate cards for startups. To date they have raised over $57m in funding from the likes of Y Combinator, Peter Thiel, Max Levchin, Yuri Milner, Elad Gil and many more incredible names. Prior to Brex, Sam Was Chief Revenue Officer at Rainforest QA. Before Rainforest, Sam saw firsthand the hypergrowth scaling of Zenefits as VP of Sales where he saw the company grow from 18 employees and $1m in ARR to over 1,800 employees and over $70m in ARR. Sam got his start in the SaaS industry with Jason Lemkin @ Echosign as Director of Sales. In Today’s Episode You Will Learn: How Sam made his way into the world of sales and came to join Jason Lemkin with his first role in sales at Echosign? Why does Sam believe that more sales reps does not always equal more revenue? What are the benchmarks that suggest founders really need to add to their sales team? Does Sam agree Founders should be selling up to $1m in ARR? How does Sam assess who is the best person to hire for the role? What have been Sam’s lessons on what it fundamentally takes to attract the best talent? In the early days how does Sam think about both role allocation and whether to hire the young jack of all trades vs the more senior executive? Why does Sam believe that founders need to spend more time on top of funnel? Why does Sam believe that not all opportunities are created equal? How does Sam think about the right structure and time it should take to pass from lead to MQL to SAL to opportunity to deal? Where does this most commonly breakdown? Why does Sam believe the key to success in SaaS sales teams is “urgency”? Literally, how can reps instil a sense of urgency in their current pipeline? Why does Sam disagree with the conventional wisdom and say discounting is a great tool? How does Sam determine the right level of discount to give? How does Sam assess pilots as an alternative approach to getting leads over the line? Sam’s 60 Second SaaStr What does Sam know now that he wishes he had known at the beginning? Quality or quantity of logos in the early days? Sales rep productivity, what does Sam believe is good? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Sam Blond This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Eoghan McCabe is the Co-Founder & CEO @ Intercom, one of the fastest growing saas companies of the day providing a new and better way to acquire, engage and retain customers. Due to their phenomenal growth they have raised over $240m in funding from some of the best in the world including Kleiner Perkins, Social Capital, Bessemer and Index, just to name a few. As for Eoghan, prior to co-founding Intercom, he founded an award-winning software design consultancy called Contrast, and co-founded Exceptional, a developer tool startup acquired in 2011 and now a part of Rackspace. In Today’s Episode You Will Learn: How did Eoghan come to be founder of one of the hottest growing startups in SaaS from founding a software design firm in Ireland? What does Eoghan believe are the core pillars for success in making the move from SME to enterprise? How does one reinvent oneself to make this transition? How has Eoghan seen te org structure and internal decision-making change with the adoption of many more enterprise clients? How does Eoghan determine between the decision to hire the young jack of all trades vs the much more experienced senior exec? Why does Eoghan believe you can never be too early to bring someone more senior than you onto the team? What makes Eoghan say, “we are all learning on the fly”? How does Eoghan look to create a culture of experimentation and accountability without the fear of failure? What must the leader do to imbue this culture? Where does Eoghan see many going wrong in trying to make this happen? How does Eoghan think about “transparency” with SaaS companies today? Why does he think that not only is it not healthy but also largely not possible? Instead, what is a better, more sustainable solution to transparency? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Eoghan McCabe This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Steve Lucas is the CEO @ Marketo, the world leader in marketing automation for companies of any size. Prior to their IPO and eventual sale to Vista Equity partners for $1.79Bn they raised over $100m in VC funding from the likes of Battery Ventures, IVP, Mayfield and Lead Edge Capital. As for Steve, prior to joining Marketo, he served in many leadership positions at SAP, Salesforce, Microsoft, BusinessObjects, and Crystal Decisions. If that wasn’t enough Steve also sits on the board of Tivo, SendGrid and The American Diabetes Society. In Today’s Episode You Will Learn: How did Steve make his way into the world of SaaS and come to be CEO @ Marketo? Why does Steve describe his experience at Salesforce to be life-changing? What were the core takeaways for Steve? How has that impacted how he operates today with Marketo? What does Steve mean when he says Marc Benioff is a “master of relevance”? Why does Steve believe the key to success as a CEO is accessibility? How can CEOs be both vulnerable and strong in today’s SaaS world? What are the 2 different types of CEOs and how they engage with their CMOs? What do the best do? What do the worst do? Why does Steve believe that the “CRM” term is incomplete? How does Steve fundamentally believe the way that customers want to be engaged with has changed? How can marketers enact this level of personalisation and engagement with such large customer bases? How does the role of artificial intelligence fit into this mass scale personalisation? How does Steve view the broader martech landscape? Why does Steve strongly believe that we will be entering a period of consolidation in martech? How does Steve view the emergence of new categories such as ABM? How does this impact his overarching view on the next wave for martech? Steve’s 60 Second SaaStr What does Steve know now that he wishes he had known when he started? Management upgrade is the most important role of CEO, agree? What keeps Steve up at night? How does that influence his running and operations of Marketo? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Steve Lucas This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Jerry Jao is the Founder & CEO @ Retention Science, the startup that brings intelligence to your marketing automation through artificial intelligence that delivers a personalized customer experience, at scale. To date, Jerry has raised over $10m in VC funding with Retention Science from great friends of the show in Forerunner Ventures, Upfront Ventures, Clark Landry, Andy Rankin and more fantastic names. Prior to founding Retention Science, Jerry founded two other e-Commerce marketing technologies and served as Strategic Innovation Officer to Clear Channel Radio. Jerry is also a Guest Lecturer at The Kellogg School of Management and sits on the board of Penango. In Today’s Episode You Will Learn: How did Jerry make his way into the world of SaaS with the founding of his first company? What have been the top 3 mistakes that Jerry has made since founding Retention Science? With P&G, Unilever and Olay all as enterprise clients, how did Jerry first sell into them as a small startup? What is required to give these large enterprises confidence in buying from startups? What does the perfect case study look like to convert these mega accounts? In the early days is it a quality or quantity of logos game? How important is it for the founder to be really actively involved in the sales process to these mega corporations? How does Jerry divide his time now between new and existing customers, as well as team and investor management How does Jerry approach multi-year and prepaid deals with these incumbents? What is the line of reasoning for suggesting prepaid is fair? Retention Science have been profitable since 2018, how does Jerry look to balance the mindset of fast growth and profitability? How does Jerry think about payback period for enterprise sales reps with this profitability mindset? How does this affect his thoughts and views on internal asset allocation? Jerry’s 60 Second SaaStr A moment in Jerry’s life that has changed the way he thinks? When I say success in SaaS who embodies this to Jerry? What does Jerry know now that he wishes he had known at the beginning? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Jerry Jao This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

David Skok is a serial entrepreneur turned VC at Matrix Partners. He founded four companies: Skok Systems, Corporate Software Europe, Watermark Software, and SilverStream Software and did one turnaround with Xionics. Three of the companies he founded went public and one was acquired. In 2001 David joined Matrix Partners, who had backed his last two startups, as a General Partner. David’s successful exits as an investor at Matrix include: HubSpot, JBoss, AppIQ, Tabblo, Netezza, Diligent Technologies, CloudSwitch, TribeHR, GrabCAD, OpenSpan and Enservio. David currently serves on the boards of Atomist, CloudBees, Digium, Meteor, Namely HR, Salsify, and Zaius. You can also find David’s amazing blog here! Huge thanks to Hardi Meybaum and Jason Lemkin for the intro to David today. In Today’s Episode You Will Learn: What are the leading indicators that early stage VCs dig deep on to assess the strength of product market fit? What level of traction both in enterprise and SMB would an early stage investor deem exciting enough to pursue? What levels of engagement are sufficient enough to suggest cause for a much larger and increased round? How should founders assess sales rep productivity? What can they do to actively shorten the ramp time? How will early stage investors analyse the ramp time? What suggests repeatability of process? Why does David believe there is no point focusing on CAC/LTV in the early days? What is the single biggest thing that founders can do to show repeatability of process and revenue as fast as possible? What is the most common reason that people miss plan? How must the mindset of the founder switch from extreme frugality to hyper growth scaling? When is the right time for this transition to take place? What are the inherent challenges to this switch? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr David Skok If you’re looking to simplify file version control, ensure data security and save time while increasing accessibility, Egnyte is the right solution for your business. Egnyte delivers secure content collaboration, compliant data protection and simple infrastructure modernization; all on a single SaaS platform. Founded in 2007, Egnyte is privately held, headquartered in Mountain View, CA and supports thousands of businesses worldwide. For more information, please visit egnyte.com/SaaStr. MonkeyLearn allows companies to easily analyze text with Machine Learning. Customers like Clearbit and Segment are using MonkeyLearn to turn emails, support tickets, customer feedback, and documents into actionable data. Their platform makes it super easy to classify texts by topic, sentiment or intent or to extract specific data such as keywords, names, and companies. MonkeyLearn makes teams more efficient by automating business processes, getting insights and saving hours of manual text data processing. And if you would like to learn more, head to monkeylearn.com/saastr, that is www. m o n k e y l e a r n .com/saastr. Plus, listeners of the SaaStr podcast will have a very special opportunity to purchase monthly plans for half the price. So, check out MonkeyLearn and start getting more out of your text today. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Dave Kellogg is the CEO @ Host Analytics, the leader in cloud-based enterprise performance management (EPM). Previously, Dave was SVP/GM of Service Cloud at Salesforce and CEO at unstructured big data provider MarkLogic. Before that, Dave was CMO at Business Objects for nearly a decade as the company grew from $30M to over $1B. Dave has also worked in various capacities with the likes of Breeze, GainSight, Tableau and MongoDB and previously sat on the boards of ag tech leader, Granular (acq by DuPont for $300M) and big data leader Aster Data (acquired by Teradata for $325M). In Today’s Episode You Will Learn: Why does Dave believe it is foundational to be an ARR first company? How does Dave think startups can show their ARR first mentality from the first investor meeting? How does this help drive operational efficiency? How does Dave segment ARR into 3 distinct camps? Why does Dave argue that SaaS metrics are not nearly as simple as they seem? Which metrics does Dave believe most founders confuse? What metrics will the best VCs pick apart and dig deep on? How can founders respond with accuracy and confidence? How does Dave respond to multi-year deals? Under what conditions are they acceptable and not acceptable? How must they be reported in accounting? Where do many startups go wrong when considering multi-year deals? How important is it for them to be pre-paid? Why does Dave argue that renewals do not measure customer satisfaction?What is an accurate measurement to determine customer satisfaction? How often should this be conducted? What sample size of customer gives the right amount of data? How does Dave approach comp with regards to sales team cross-sell and upsell? Why is it not as black and white as boards often portray? Under which circumstances does Dave believe double comp is justified and not justified? How can you communicate this to your board successfully? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Dave Kellogg If you’re looking to simplify file version control, ensure data security and save time while increasing accessibility, Egnyte is the right solution for your business. Egnyte delivers secure content collaboration, compliant data protection and simple infrastructure modernization; all on a single SaaS platform. Founded in 2007, Egnyte is privately held, headquartered in Mountain View, CA and supports thousands of businesses worldwide. For more information, please visit egnyte.com/SaaStr. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Phil Fernandez is a Silicon Valley veteran, with more than 35 years of experience building and leading breakout technology companies. Phil co-founded Marketo in 2006 and led the company as Chairman and CEO for a decade, overseeing its successful IPO and acquisition by Vista Equity Partners. Prior to Marketo, Phil served as president and COO of Epiphany, an enterprise customer relationship management (CRM) software company. Today, Phil is a Venture Partner with Shasta Ventures, the fund with a portfolio including the likes of Nest, eero, Zuora, Canva and many more incredible companies. In Today’s Episode You Will Learn: When is the right time to hire your first CRO? Where did Phil make a big mistake in who owns what revenue numbers? What are the traits that make the best CROs? How should they look to work with both sales and marketing to drive efficiency internally? Why does Phil believe you must hire the most senior Chief People Officer as soon as you can? What does the role of “Chief People Officer” really embody? How should they look to work with HR internally? Who should they report to? How does this role change with a scaling organisation? How has Phil seen the relationship between average contract value and potential for expansion change? What is the correlation between and ongoing services component and both customer NPS and expansion? Where did Phil go wrong with this at Marketo? How should emerging SaaS startups today be thinking about technical legacy debt? Why does Phil believe it is never to early to have a Head of Research function? How should this function work with the team to build the latest technology into new products? Why did Steve sell Marketo to Vista Equity Partners? What was the thesis and big learnings from that experience? What does Phil mean when he says he did not “watch the clock properly’’? How can founders today be proactively thinking about ramp time for sales reps, new product engagement etc. If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Phil Fernandez This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Bill Binch is a leader and expert in the SaaS sales industry, currently CRO @ Pendo.io, the startup that helps you understand and guide your users, creating a product experience they can’t live without. They have raised over $58m in VC funding from some of the best in their space with the likes of Battery Ventures, Spark Capital and Salesforce Ventures, all backing them. As for Bill, prior to Pendo, Bill was the Senior Vice President of Global Sales at Marketo for 8 years. He joined when it was a small venture-backed startup with a mission to reinvent marketing automation. It was his sales leadership and expertise that formed a critical component in building Marketo into one of the fastest-growing enterprise software companies in the world, recognized through his being awarded worldwide VP of sales in 2011. In Today’s Episode You Will Learn: How Bill made his way into the world of SaaS and came to be employee #18 at Marketo before making the transition to today, as CRO @ Pendo? Bill has said before that career paths are for B players. First, what is wrong with the current thinking around career paths? Why does that inherently mean that A players do not align with them? How can one determine when is the right time to step away from the career paths? What characteristics and attributes do those truly special opportunities have? Bill has successfully made the transition from transactional business to enterprise business many times, what have been his core learnings on what it takes to make this transition successfully? What are the biggest challenges in making the transition? How does the internal structure of the team change when making this transition? What does Bill mean when he says you have to “rig the recruiters”? What incentives can be placed in front of them that ensure you will be a priority for them? On the flip side, what incentives do you have to give the recently on boarded employees to encourage grassroots, word of mouth on the company brand? How does the company and sales cycle fundamentally change when moving from $0-1m ARR? What does that mean for the company policy on discounting and pilots? How does the company alter when transitioning from $1-10m in ARR? How can sustainable social validity be built in this stage? How does a company successfully move from $15m-100m in ARR? 60 Second SaaStr? What does Bill know now that he wishes he had known at the beginning? What keeps Bill up at night? What does Bill mean when he says you have to check your ego? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Bill Binch If you’re looking to simplify file version control, ensure data security and save time while increasing accessibility, Egnyte is the right solution for your business. Egnyte delivers secure content collaboration, compliant data protection and simple infrastructure modernization; all on a single SaaS platform. Founded in 2007, Egnyte is privately held, headquartered in Mountain View, CA and supports thousands of businesses worldwide. For more information, please visit www.egnyte.com/SaaStr. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Kristina Shen is a Partner @ Bessemer Venture Partners, one of the world’s leading venture funds with a portfolio including the likes of Pinterest, Skype, Box, LinkedIn, Yelp and many more incredible companies. As for Kristina, she serves on the boards of DoubleDutch, Glint, Retail Solutions and Zoosk and is also a board observer with RainforestQA, Vidyard, Gainsight and ServiceTitan. Kristina is also one of the best data gurus as the co-author of Bessemer’s State of the Cloud 2016 and 2017 and Bessemer 10 Laws of Cloud, which captures the top trends among leading public and private cloud computing and enterprise mobile companies. Due to Kristina’s success she has been named to both Forbes and Business Insider’s 30 Under 30 in 2014 and 2016, respectively. In Today’s Episode You Will Learn: How Kristina made her way into the world of cloud investing and came to be the data guru for much of the cloud landscape? What does Kristina fundamentally mean when she states the key question is, is there velocity in this SaaS business? Is velocity just about revenue or ARR growth? How can startups present real velocity with their sales funnel? How can startups present further velocity through their SQL process? Why does Kristina believe that “private SaaS multiples are not expensive and we need a new framework”? What makes the existing framework inaccurate? What does this mean for the way Kristina assess ARR multiple and growth rates? How does this framework alter Kristina’s perception of the often hailed “Rule of 40”? How does it change with scaling? What are the core elements Series A SaaS investors focus on today? With regards to revenue benchmarks for the A round, where do they need you to be both on the low and high end? Where do Series A investors expect startups to be for y/y ARR growth? What core metrics are required to successfully raise your Series B in SaaS today? What does Kristina think is the fundamental difference between Series A and B today in SaaS? What can founders do to show repeatability and reliability of revenue streams as they move into the B round? 60 Second SaaStr? What does Kristina know now that he wishes he had known at the beginning? Questions from Jeremy Levine: What would Kristina like her legacy to be as an investor in 20 years time? What keeps Kristina up at night? Is it worse to see an amazing deal and pass on it or to have never seen it at all? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Kristina Shen This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Jason Lemkin is the Founder @ SaaStr, the world’s largest SaaS event with over 20,000 of the world’s best SaaS founders and investors attending every year. Jason also invests from SaaStr’s debut $70m fund and has made prior investments in the likes of Algolia, TalkDesk, MixMax, Rainforest QA and many more incredible companies. In Today’s Episode You Will Learn: How does Jason think founders should approach long sales cycles in the early days? Why does Jason believe that ultimately long sales cycles do not matter? What can the truly great VPs do to impact those long sales cycles? How does Jason think founders can tackle lead optimisation with their team? How can founders determine which leads to send to which AEs? What will the effect of this tailored lead distribution be? When is the right time for the founder to begin to take a step back from sales? Why does Jason believe that the founder must always be involved in the sales process? How does this look at scale when selling to thousands of customers? How does this mean the founder works with the growing scaling team over time? Why does Jason believe that SaaS companies have to raise so much money today? What is the core decision that founders must make when determining how much they need to raise? How should founders approach the topic of cloning? What are the 3 core advantages they have over their clones? What must they be mindful of when being cloned by incumbents? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Timo Rein is the Founder & CEO @ Pipedrive, the startup that helps sales people focus on actions that close deals. To date, Timo has raised over $30m from the likes of Atomico, Bessemer Venture Partners, TransferWise Founder Taavet Hinrikus and Andy MCloughlin and has scaled the team to over 330 people across multiple continents. Prior to founding Pipedrive, Timo was a Partner @ Vain & Partners acting in a consultancy role on how to get the best ROI from your sales process and before that was himself a door-to-door salesman with SouthWestern Company selling high ACV products. In Today’s Episode You Will Learn: How Timo made his way into the world of SMB CRM with the founding of Pipedrive from the days of being a door-to-door salesman of high ACV products? Why did Timo choose to go global with Pipedrive from day 1? What are the benefits of founders having this global mindset from the start? What are Timo’s biggest learnings in terms of acquiring customers globally early on? What worked? What did not work? How did Timo think about pricing on an individual country perspective? What are the challenges with this? Having raised from both US and UK VCs, how does fundraising differ when comparing Europe to the US? If Timo had to say the West Coast, East Coast and European VCs each had one area they focus, what would that area be? What are the challenges with these inherent focus points? What advice would Timo have for foreign founders looking to make it big in the US? How does Timo look to manage a team so spread across the globe? What are the core challenges of this? What works? What does not work? What functions can be split up by geography? What must remain in one location? Now at 300 people, how does Pipedrive ensure for the same values fit when hiring at scale? Many VCs say with such low ACV and such high churn, the SMB market is too difficult. How does Timo respond to this? How does Timo think about ensuring the continuous refilling of top of funnel? How does Timo think about acquiring such small customers in a cost efficient manner? 60 Second SaaStr? What does Pipedrive look like at $100m ARR? What keeps Timo up at night? Who is Timo’s favourite angel investor? What does Timo know now that he wishes he had known at the beginning? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Timo Rein This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com