The Official SaaStr Podcast: SaaS | Founders | Investors

Join Molly Ford, Salesforce Global Equality Programs Senior Director, and Leyla Seka, Salesforce VP of Mobile for actionable advice they have applied on their own journey. Here are their lessons learned on driving change in gender equality, equal pay and racial equality within Salesforce. Missed the session? Here's what Molly and Leyla talk about: Building a community of allies and allyship How to drive equality What you can be doing as an employee to help drive the culture you want 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 Molly Ford Leyla Seka

Parker Conrad is the Founder & CEO @ Rippling, the startup that gives you back your time from payroll to employee computers, Rippling makes it unbelievably easy to manage your company's HR and IT - in one system. To date Parker has raised over $59m in funding from some of the best in the business including Mamoon @ Kleiner Perkins, Garry Tan @ Initialized, Justin Kan, SV Angel and Y Combinator, just to name a few. As for Parker, prior to founding Rippling, he was the Founder & CEO @ Zenefits, the startup he built from $0 to $60m in ARR in just 3 years. Before that he co-founded Sigfig where he grew assets on the platform to over $35Bn across 500k users. In Today's Episode We Discuss: How Parker made his way into the world of startups and SaaS, came to found Zenefits and what was that a-ha moment for the founding of his most recent company, Rippling? What does Parker do with regards to operational scaling that is unconventional but works? Why does Parker believe it is fundamentally better to wait for as long as possible before hiring customer support? Why should engineers also be doing customer support? Why should your engineers be heavily involved in the customer support hiring process? What are the benefits of this? How can one prevent their customer support team from being a wall of protection for the product and eng team? How can you ensure seamless collaboration and communication flow between product and customer support? Stripe last week recently announced their 5th office would be… "remote", so how does Parker feel about the building of remote teams? What are the most important things when establishing your first remote team? What do you look for in those hires? What can be done to ensure a greater feeling of community and closeness despite the distance? What have been some of the biggest challenges for Parker in building out the remote team? Parker has been a CEO with 3 different companies now and so how has he seen his style and approach change over the years? What has Parker found the hardest to get good at? When advising founders on fundraising, what advice does he give? How can founders know when is the right time to raise? How should they look to build relationships with investors between raises? 60 Second SaaStr: What does Parker know now that he wishes he had known in the beginning? What one thing would Parker like to change about tech and Silicon Valley? Biggest mentor and what has Parker learned from them? Read the full transcript on our blog. 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 Parker Conrad

Join Logikcull's CEO and Co-Founder Andy Wilson as he takes you through the mistakes made going from $0 to $10M in 19 months. Missed the session? Here's what Andy talks about: Selling the way your customers want to buy. What you need to know about hiring, firing, advisors, and culture Why SaaS is your business model, not your mission. 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 Andy Wilson

Andrew Filev is the Founder & CEO @ Wrike, the cloud based collaboration and project management software that scales across teams in any business. In Dec 2008, Vista Equity Partners acquired a majority stake in Wrike for a deal reportedly valuing the company at $800m. Before this transaction, Andrew had raised over $45m in funding from the likes of Rory @ Scale and Bain Capital Ventures just to name a few. As for Andrew, he started his first software development company at the age of 18 and has been running Wrike for the last 13 years alongside advisory roles with both Ditto and Appulate. In Today's Episode We Discuss: How Andrew made his way into the world of SaaS from his starting his first software business at the age of just 18 and how that led to his founding of Wrike? How does Andrew advise founders on the question of whether to start in enterprise or SMB? What are the benefits of starting in SMB? How does the founder know when is the right time to start moving to enterprise? What are those leading indicators? How does the product and what you invest in proactively need to change as you move into enterprise? Andrew has been the CEO for the last 13 years, how has the role of CEO changed over those years? What has been the most challenging phase? If the CEO is the guardian of the culture, what does a great guardian look like? What 3 elements does Andrew focus almost exclusively on today within his role as CEO? What does Andrew think are the major breaking points in the scaling of companies? Where does culture begin to breakdown? What can be done to mitigate this? How does Andrew think about using employee satisfaction surveys internally? How can one accurately determine the strength of your manager set? Andrew's 60 Second SaaStr: What does Andrew know now that he wishes he had known at the beginning? No man's land in SaaS pricing, does it exist? Sales rep productivity, what is good to Andrew? Read the full transcript on our blog. 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 Andrew Filev

Duo Security Co-Founder and CEO Dug Song and PagerDuty CEO Jennifer Tejada discuss building, enabling, and leading great teams through 10K+ customers, $100M+ ARR, $1B+ valuation and beyond - all while earning 4.5+ Glassdoor company ratings and 98%+ CEO approvals from 500+ total employees! Duo Security is a cloud-based provider of unified access security and multifactor authentication was acquired by Cisco for $2.35 billion in October 2018. PagerDuty is a leading digital operations management platform for organizations announced new financing in September 2018 at a $1.3 billion valuation. Missed the session? Here's what Jennifer and Dug talk about: When is the right time to raise money? How can you better manage the board? Should you worry about competitors? 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 Jennifer Tejada Dug Song

Godard Abel is the Founder & CEO @ G2, the company helping millions of business make better product buying decisions every month. To date, Godard has raised over $100m in funding with G2 from the likes of Accel, IVP, High Alpha, Pritzker Group and Chicago Ventures just to name a few. As for Godard, he founded his first business, BigMachines, in 2000, a business he scaled to $50m in revenue and over 300 people up until it's acquisition to Oracle 11 years later for $400m. Godard then became CEO @ Steelbrick where he took them from 5 to 200 employees and increased bookings by 37x in 7 quarters. Steelbrick was ultimately acquired by Salesforce where he spent a year and a half before starting G2. In Today's Episode We Discuss: How did Godard make his way into the world of SaaS over 20 years ago? What was the a-ha moment for the founding of G2 for Godard? Having been a Founder through the bust of 2000, how did seeing that macro environment impact his operating mentality today? What did it teach him about capital efficiency and investing ahead of time? Taking the team from 70 to 20, what were his lessons on the right way to let someone go? Where do many people get it wrong today? Why does Godard advocate for working with people that you have worked with before? How can you find the zone of genius for the people that you work with? How does Godard set a culture of ambition and determination around goals but also prevent dejection if the goals are not hit? How often should rep quota be hit? Why is that the right ratio? Where does Godard believe that things really start to break down in the scaling of an organisation? What can you do to get ahead of those moments and minimise their impact? How many direct reports does Godard believe is the optimal and then the maximum for a manager to have? How have his thoughts on this changed over time? Godard's 60 Second SaaStr: What would Godard like to change in the world of SaaS today? What does Godard know now that he wishes he had known at the beginning? If an investor can provide one value, what would it be and why? Read the full transcript on our blog. 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 Godard Abel

Dave Kellogg is CEO of Host Analytics and prolific blogger. Join him as he takes you through lessons learned from Host Analytics on the top questions every SaaS CEO wrestles with. Dave was CEO of Host Analytics from 2012 to 2018 where he quintupled ARR while halving customer acquisition costs in a highly competitive market, ultimately selling the company in a private equity transaction. Missed the session? Here's what Dave talks about: When is the right time to raise money? How can you better manage the board? Should you worry about competitors? 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 Dave Kellogg

Jason Reichl is the Founder & CEO @ GoNimbly, the first SaaS consultancy to focus on revenue operations. Currently growing 100% year over year, working with companies to un-silo their operations and create one strategic revenue ops team to support their Go To Market strategy. In the past, Go Nimbly has helped companies like Zendesk, Twilio, PagerDuty and Coursera to achieve alignment and increase revenue by 26%. As for Jason, prior to co-founding GoNimbly, he was Director of Product Management @ TradeShift and before that was VP of Product Management @ Lanetix. In Today's Episode We Discuss: How Jason made his way from Director of Product Management at Tradeshift to changing the way we think about scaling revenue operations with GoNimbly? Why does Jason believe that we have to remote handoffs between go to market teams? Why are they so damaging? How does Jason believe SaaS companies can use a "swarming" effect to create the best buyer experience for their customer? What does this involve? How does this change the type of metrics that we track? Why does Jason believe that your North Star has to be revenue in the go to market teams? Why does Jason also believe that it is damaging to have the same North Star across the entire company? How should North Star's be segregated between GTM teams and biz ops teams? What are the mistakes many companies make when setting their internal North Stars? Why does Jason believe that alignment is a dirty word? Why is alignment actually a negative for the customer experience? What does Jason view as vanity metrics? If one has vanity metrics in place, what does Jason recommend as to keeping them or phasing them out? 60 Second SaaStr: What does Jason know now that he wishes he had known in the beginning? How does Jason feel about multi-year deals? How does Jason feel about channel/partner sellers? Read the full transcript on our blog. 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

We live in a Shark Tank world: competition is fierce, talent is better than ever, and we're all striving to come out on top. CEOs everywhere are seeking to innovate, but 81% say their teams are not equipped to meet the challenges needed to compete in today's marketplace. Innovation is about empathy with your customers. It's all about customer obsession! In this session, Sandy Carter, AWS Vice President will hone your superpower - not of customer focus, or customer driven, but customer obsessed. Missed the session? Here's what Sandy talks about: How to start with success and think backwards Think about how to present a feature or product before you start building. 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 Sandy Carter

Manny Medina is the Founder & CEO @ Outreach, the market leading sales engagement platform that turns your team into a revenue driving machine. To date, Manny has raised over $114m in funding from some great people including friends of the show in the form of Alex Clayton @ Spark, Mayfield, Trinity Ventures and DFJ Growth, just to name a few. Prior to founding Outreach, Manny spent 7 years with Microsoft where he ran the Latin America and Canada business development group for Microsoft's emerging mobile division, representing $50M of yearly revenue. Befofe that Manny was a Senior Product Manager @ Amazon where he engineered the compensation system for Amazon Associates and Web-Services which accounts for 15% of Amazon's traffic. In Today's Episode We Discuss: How Manny made his way to found the leader in sales engagement from product management at Amazon and Business Development @ Microsoft? How does Manny fundamentally approach managing top of funnel? What are the 2 big dangers of not managing it aggressively? What can be done to ensure not only full but high quality top of funnel? Why does Manny believe it is so important to track pipeline coverage as one of your core metrics? What does good look like when it comes to pipeline coverage? How does this change if you are creating vs in an existing market? How does Manny think about specialisation within the sales function? Why are SDR's 99% of the time not able to carry leads to completion? How does Manny think about quota construction today? Does Manny err on the side of setting high to be ambitious or setting low to increase confidence? How can managers really empower their reps to be aggressive in hitting their quota and exceeding it? How does Manny think about resource allocation on the individual rep level? What is sufficient? What is excessive? Does Manny believe that the founder should always be responsible for selling their product at one moment in time? How did Manny sell the first $1m in ARR simply through walking the streets of SOMA and selling door-to-door? What were his biggest lessons from doing this? Why does Manny believe that you should not have a VP before $5m? 60 Second SaaStr: What does Manny know now that he wishes he had known in the beginning? What does the future of sales prospecting look like to Manny? What would Manny like to change about the world of SaaS today? Read the full transcript on our blog. 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 Manny Medina

Join Glitch CEO Anil Dash and Twilio CEO Jeff Lawson for a discussion about the ethical implications of technology in today's society. Jeff and Anil discuss how social media and AI are changing the way we think about the impact of technology on society as well as the responsibility of tech leaders for this impact. Missed the session? Here's what Jeff talks about: How taking no stance as a business leader today, is taking a stance How to set concrete numbers for diversity goals The impact of corporate culture on employee happiness 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 Jeff Lawson Anil Dash

Alexandr Wang is the Founder & CEO @ Scale, the startup providing high quality training and validation data for AI applications. To date, Alexandr has raised over $23m with Scale from some of the best in the business including Index, Accel, Y Combinator, Dropbox's Drew Houston, Justin Kan, Thumbtack's Jonathan Swanson and more. Prior to founding Scale, Alexandr was a Tech Lead at Quora, directly responsible for all speed projects and before that a software engineer at Addepar responsible for building and maintaining financial models. In Today's Episode We Discuss: How did Alex make his way into the world of SaaS and come to found Scale? What were some of his biggest takeaways from seeing the first hand scaling of Quora and Addepar? Why does Alex take the contrarian view that "TAM in the traditional sense barely matter"? What two characteristics of the market should founders really look to examine? How does Alex approach the element of market sizing? Does he prefer top down or bottoms up and why? Why does Alex believe that you must invest in customer success before you think you need it? What were the benefits for Alex of investing early in customer success? Why does CS over sales ultimately drive the growth of your company? How does one know when is the right time to hire their first in customer success? What is the ideal profile of this candidate? How does Alex think about the integration of customer success and product teams? Why is it crucial from the product perspective that founders pick their first customers well? How can your customers drive your product decisions? How can one ensure to be customer informed and not customer driven? Why does Alex believe that in the early days it is not important to focus on the size of the deals you are signing? What should founders be focusing on with these early customers instead? When is the right time to flip the switch and opt for value extraction as a more primary objective? How does Alex respond to the fact that VCs often look at these first customer deals as an indication of the size of the pain point you are solving? 60 Second SaaStr: What does Alex know now that he wishes he had known in the beginning? What does Alex believe is the hardest role to hire for today? Who does Alex think is crushing it in the world of SaaS today? Read the full transcript on our blog. 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 Alexandr Wang

Leela Srinivasan is the CMO of SurveyMonkey. Join her as she takes you through her seven tips for using customer feedback and building rabid fans. Consistently ramping your ARR is a whole lot harder if your customers don't stick around. In an age where earning customer loyalty and trust is harder than ever, the road to lifetime value is paved with customer feedback. If you take the time to listen, understand and act on what your customers are thinking and feeling, you'll create an army of advocates and drive topline revenue growth for good measure. Missed the session? Here's what Leela talks about: How to create an army of advocates How to drive topline revenue growth Real world examples from businesses that are listening and acting on customer feedback every day. 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 Leela Srinivasan

Stephen Burton is VP of Smarketing at Harness, the industry's first continuous delivery as a service platform. To date, Harness has raised $20m in funding from the wonderful Matt Murphy @ Menlo Ventures and BIG Labs. Prior to Harness, Stephen was VP of Marketing at Glassdoor, managing a team of 52 in product marketing, helping grow B2B revenue from $19m to $90m in just 2 years, leading to their $1.2Bn acquisition. Before Glassdoor, Stephen was VP of Product Marketing at AppDynamics where he helped grow B2B revenue from $0 to $100m in a staggering 3 year period, resulting in their $3.9Bn acquisition by Cisco. In Today's Episode We Discuss: How Steve made his way into the world of SaaS and came to be VP of marketing at 2 of the larger B2B exits of the last decade in AppDynamics and Glassdoor? What were Steve's biggest takeaways from seeing the hyper-scaling at AppDynamics? Steve has previously said, "sales and marketing must be one team". Why does he believe this is so important? What can leaders do to turn this into reality? What works? Where has Steve seen many make mistakes? Where does Steve find common points of tension between sales and marketing? WHat are the 3 elements that marketing comp should be tied and aligned to? What does Steve mean when he says, "marketers need to embrace the developer first mindset"? What does this mean for the processes used by marketing teams? Speaking of developer-first, how can startups compete in a war for talent against FB and Google? How can they integrate autonomy into their hiring process as a core advantage? For Steve, what does devops really mean? What does Steve believe is the right culture for devops teams? Does it differ from traditional dev teams? How can a CEO determine when is the right time to fundamentally invest in devops? What are the required steps to make devops teams as successful as possible? 60 Second SaaStr: What does Steve know now that she wishes she had known at the beginning? When is the right time to pour fuel on the company fire? The playbook? Is there one? Dangers? Copyability? What would Steve most like to change in the world of SaaS? Read the full transcript on our blog. 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 Stephen Burton

Mikkel Svane is the CEO of Zendesk and author of "Startupland". Join him as he takes you through his lessons taking Zendesk beyond a billion in ARR. Mikkel founded Zendesk in Copenhagen, Denmark in 2007 before moving the company to San Francisco in 2009. Missed the session? Here's what Mikkel talks about: The future of the cloud The rise of the public cloud and re-platforming of the tech stack How business applications are sold and delivered leveraging 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 SaaStr Mikkel Svane

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

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? Read the full transcript on our blog. 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

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

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? Read the full transcript on our blog. 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

At Atlassian, openness is core to everything the company does: employees can access most information on Confluence; "open company, no bullshit" 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

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? Read the full transcript on our blog. 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

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

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? Read the full transcript on our blog. 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

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

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? Read the full transcript on our blog. 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 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? Read the full transcript on our blog. 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

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? Read the full transcript on our blog. 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

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? Read the full transcript on our blog. 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 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? Read the full transcript on our blog. 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

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? Read the full transcript on our blog. 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

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? Read the full transcript on our blog. 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

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? Read the full transcript on our blog. 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

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? Read the full transcript on our blog. 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

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? Read the full transcript on our blog. 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

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? Read the full transcript on our blog. 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

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? Read the full transcript on our blog. 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

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? Read the full transcript on our blog. 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

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? Read the full transcript on our blog. 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 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? Read the full transcript on our blog. 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

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? Read the full transcript on our blog. 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

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? Read the full transcript on our blog. 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

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? Read the full transcript on our blog. 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

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? Read the full transcript on our blog. 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

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? Read the full transcript on our blog. 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

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? Read the full transcript on our blog. 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 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? Read the full transcript on our blog. 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

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? Read the full transcript on our blog. 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

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? Read the full transcript on our blog. 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

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? Read the full transcript on our blog. 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

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? Read the full transcript on our blog. 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