The Official SaaStr Podcast: SaaS | Founders | Investors

Today’s show is centred around The Top 10 VP of Sales Lessons Learned In Scaling To $100M ARR. Leading this conversation is Aaron Ross, author of best selling book, Predictable Revenue, providing the framework for the outbound process & sales team Aaron created for Salesforce.com. During his time at Salesforce as Director of Corporate Development and Acquisitions, Aaron added an extra $100 million in revenue in just a few years. Joining Aaron from the sales perspective we have Andrew Bothwell, VP of Sales @ TalkDesk and Aaron Schilke, VP Enterprise Sales @ Talkdesk, one of the fastest growing SaaS startups today. Providing insight from the other side of the table we have Josh Stein, Partner @ DFJ where his current board responsibilities include Box (NYSE: BOX), Chartbeat, LaunchDarkly, LendKey, SugarCRM, and previous guest with me on SaaStr in Talkdesk. But enough from me so without further ado I am going to hand over the reigns to Aaron Ross. In Today’s Episode You Will Learn: What does Josh Stein believe is the toughest growth stage in SaaS? Which stage separates the men from the boys? Why is growing to 100 a case of simple maths? How does this maths affect how you should think about your sales hiring pipeline? How does this maths affect your view of forecasting? How do TalkDesk look to build a repeatable and scalable sales process? What have been their major learnings? Where do most startups make mistakes and falter? How should VPs of sales approach feedback with their reps? Why has a VP failed if a rep is blindsided by a particular piece of feedback? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Edith Harbaugh is the Founder & CEO @ LaunchDarkly, the startup that allows you to fearlessly and swiftly release software by separating feature rollout from code deployment. They have raised over $10m in funding from many previous guests of The Twenty Minute VC including Andy McLoughlin @ SoftTech, Josh Stein @ DFJ and the wonderful team at Bloomberg Beta. As for Edith, prior to LaunchDarkly, she was a Director of Product @ Tripit and Concur. Edith also holds two patents in deployment from her time in engineering at Vignette. In Today’s Episode You Will Learn: How Edith made her way into the world of SaaS and came to found LaunchDarkly? Does Edith agree with Jason Lemkin that the hardest element is the 1-10 customer phase? How has Edith navigated this process with her differing companies? How does Edith look to structure her sales team to successfully close Fortune 500 deals? What is the fundamental difference in selling to enterprise rather than SMB? What can founders do to make NPS a more intelligent metric? How can NPS be analysed effectively to tell you more about the state of your business? What are the signs of a truly great sales person? How do they aid not only their company but the customer they are serving? What is their required knowledge base? 60 Second SaaStr What is Edith’s fave SaaS resource? What does Edith know now that she wishes she had known before? Oakland Office: Why not SF? What are the benefits? 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 Edith Harbaugh This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Lauren Vacarrello is VP of Marketing @ Box, one of the leading enterprise B2B brands today. At Box, Lauren leads a 50 person team that involves demand generation, global campaigns, events and more. Prior to Box, Lauren was VP of Marketing @ Adroll, where she built and scaled a 25 person global marketing team from the ground up. If that was not enough, Lauren is also the Co-Author of “The Retargeting Playbook” and “Complete B2B Online Marketing”. In Today’s Episode You Will Learn: How does Lauren view the relationship between sales and marketing? Why does Lauren believe the ARR pipeline is not just the responsibility of the sales team? Why is lead nurturing not just about email? What are the other core components to ensure successful progression of leads through the funnel? How does Lauren view successful lead segmentation? Why does Lauren like to segment leads into 3 distinct buckets? How does this strategy play out at different ends of the market? What is the role of marketing post-purchase? How has Lauren seen this change since the early days of her career? How does this differ when comparing SMB to enterprise? 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 Lauren Vaccarello This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Aaref Hilaly is a Partner @ Sequoia Capital, one of the world’s most successful VC funds with investments in the likes of Apple, Google, Paypal, Whatsapp and LinkedIn just to name a few. As for Aaref he came to the valley with 2 suitcases and the ambition to start a company. That he did and had 2 companies that were Sequoia backed, first CenterRun and then ClearWell Systems where Aaref was instrumental in the company’s growth from 0 to a $100m revenue run rate in just 4 years, prior to their $410m acquisition by Symantec. Today Aaref draws on this incredible operational success to illustrate how to manage up and have a very happy board. In Today’s Episode You Will Learn: Why does Aaref advocate for founders not to manage the board but to engage them? How can this be done effectively? What does Aaref state are the dangers of focussing on metrics with your board? Why should you focus on product instead? How does this shift change the dialogue with the board? When things do go wrong and the company misses a quarter, how should the founder react? Why does Aaref suggest that founders need to own the miss? How should they structure these conversations? What should they not do when they miss a quarter? How can founders most effectively put their board to work? How should this be communicated and then followed up on by the founder? Where has Aaref found the board can provide the most value? 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 Aaref Hilaly This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Mark Roberge is a Senior Lecturer @ Harvard Business School where he teaches entrepreneurial sales and marketing. Prior to his role with HBS, Mark was the Chief Revenue Officer @ Hubspot where he increased revenue over 6,000% and expanded the team from 1 to 450 employees. As a result, Mark has been named Forbes' Top 30 Social Sellers in the World and awarded the 2010 Salesperson of the Year by MIT. Michele Law is an investor and advisor specialising in building and executing on go to market strategies, creating new revenue models and the operations to support them. Michelle has sat on both sides of the table having been a Principal at Greylock for 8 years before moving to be COO at OpenDNS where she led the sales and customer success team growing enterprise revenue from $0 to $20M ARR in 4 years, prior to the company’s acquisition by Cisco for $635m. Michele then moved to Castlight Health where she grew revenue from $13 to $75m. In Today’s Episode You Will Learn: Why it is fundamentally dangerous to prematurely focus on growth? How can founders know when is the right time to focus on growth? What does the path to growth phase look like? How should founders assess and structure the core components: customer success, unit economics and growth? In which order should they be prioritised? What does the funnel look like? What should the profile of your first sales hire be? How can founders understand who and when to hire? From Hubspot days, when has Mark seen the transition from generalist to specialist? What should your sales compensation plan look like in the early days of the company? Why does Mark believe that churn is rooted in the sales compensation plan? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Todd Olson is the Founder & CEO @ Pendo, the startup that allows you to capture all user behaviour, gather feedback and then provide contextual support. They have raised over $30m in VC funding from some of the very best in the business including Neeraj @ Battery Ventures, Megan @ Spark and Matt @ Salesforce Ventures just to name a few. As for Todd, prior to Pendo he held various different roles in product as well as co-founding 2 prior startups. In Today’s Episode You Will Learn: How did Todd make his way into the world of SaaS and come to found Pendo? Why does Todd believe that there is inherent tension between customer success and product teams? How has this changed from sales and marketing team tension? What does Todd suggest to mitigate this tension? How does Todd evaluate his hiring process? At what stage does one become a specialist vs a jack of all trades? Why does Todd always believe that you should hire ahead of where you are? Todd has previously said that ‘money is not all the same’. How does Todd look to select his investors? What value adds are most desired for Todd? What do the best investors do that make them so? 60 Second SaaStr What does Todd know now that he wishes he had known in the beginning? What is Todd’s favourite SaaS reading material: Mattermark Daily, Tom Tunguz Creating a startup culture for adults? 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 Todd Olson This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Amit Agarwal is the Chief Product Officer @ Datadog, the startup that provides cloud scale monitoring that tracks your dynamic infrastructure and applications. They have raised over $140m in VC funding from some of the best in the business including Index Ventures, IA Ventures, OpenView and RRE just to name a few. As for Amit, before Datadog, Amit was the Director of Product Management at Quest Software (now Dell), where he led the team responsible for application performance monitoring. Previously, Amit held product management roles at Datamirror (now IBM) and Embarcadero Technologies. In Today’s Episode You Will Learn: How did Amit make his way into the world of SaaS and come to be Chief Product Officer @ Datadog? Why did Datadog not have a marketing strategy for the early days? What would Amit advise early stage founders with regards to optimising their marketing in the early days? Obviously a multi-product line is crucial for a SaaS startup to be successful, what is Amit’s take on how, when and why to launch a second product? What have been his big learnings on this from Datadog? Amit has said before that it is tough to sell to large enterprises in the early days, does that mean startups should always start with SME’s? At what price point does it become a challenge? Does Amit agree that if you are between 25K-100K you are in the valley of death price wise? 60 Second SaaStr What does Amit know now that he wishes he had known in the beginning? What is Amit’s favourite SaaS reading material? When is the right time to hire a CPO and why? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Amit Agarwal This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Tim Eades is the CEO @ at vArmour, the industry's first distributed security system that provides application-aware micro-segmentation. Tim joined vArmour as CEO in October, 2013. Prior to that, he was the CEO at Silver Tail Systems until the company was acquired by RSA, the security division of EMC in late 2012. Prior to leading Silver Tail Systems, Tim was CEO of Everyone.net, an SMB focused SaaS company that was acquired by Proofpoint. Tim has also held sales and marketing executive leadership positions at BEA Systems, Sana Security, Phoenix Technologies and IBM. In Today’s Episode You Will Learn: How did Tim make his way from punk rock fan in the UK to leading Silicon Valley CEO? Why does Tim believe Incremental Account Opportunity (IAO) is one of the most important metrics for a growing startup? Why does Tim believe that most founders are far too late to ship their second product? How can they identify adjacent markets? When exactly is the right time to know when to ship your second product? What does it take in terms of sales team structure to successfully orchestrate the 7 figure deals that Tim does? What does that look like in terms of sales team compensation? 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 Tim Eades This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

David Rodnitzky is founder and CEO of 3Q Digital, a leading digital agency that was acquired by Harte Hanks in 2015. Prior to 3Q Digital, he held senior marketing roles at several Internet companies, including Rentals.com (2000-2001), FindLaw (2001-2004), Adteractive (2004-2006), and Mercantila (2007-2008). David currently serves on advisory boards for several companies, including Marin Software, MediaBoost, Mediacause, and a stealth travel start-up. Loretta Jones is the vice president of marketing at Delighted, the fastest way to gather customer feedback and put it into the hands of those who can act on it. Prior to Delighted, Loretta's marketing programs grew Insightly, a CRM for small business, from 100,000 users to over 1.2 million users. Prior to Insightly, Loretta worked at Adobe Sign (formerly Adobe EchoSign) and grew the EchoSign brand to $25 million. In Today’s Episode You Will Learn: Should all companies invest in SEM? How does SEM differ for SaaS SMB businesses vs enterprise SaaS businesses? How much of a role should iterating and testing play with regards to SEM? What are the strategies that can be used to ensure for maximal dollar efficiency? David has said before that ‘no demand channel is an island’. How does SEM work together with the other channels (SEO, display ads etc) to form a cohesive marketing strategy? As LTV takes a considerable time to figure out and can be inaccurate, should startups focus on their CPA (cost per acquisition) more than any other metric? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr David Rodnitzsky This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Tom Tunguz is a Partner at Redpoint Ventures and one of the pre-eminent thought leaders in the rise of SaaS. Tom has made investments in the likes of Demio, Axial, Chorus.ai and more incredible companies. Tomasz is also the co-author of Winning with Data: which explores the cultural changes big data brings to business, and shows you how to adapt your organization to leverage data to maximum effect. Before joining Redpoint, Tomasz was the product manager for Google’s AdSense social-media products and AdSense internationalization. If you have not checked out Tom’s blog that is a must and can be found here. In Today’s Episode You Will Learn: What are the 4 dominant ways startups are incorporating machine learning into their feature set? Why does Tom not believe in AI and discuss prefers to discuss machine learning? What 3 things have caused the rise of machine learning? Why now will machine learning happen in core categories in SaaS? What role does deep learning play in this rise? What are the 5 precepts of the type of companies that Tom wants to invest in using ML in SaaS? Why should startups discuss their value proposition over their technology? How does Tom advise startups can gain access to proprietary datasets? How would Tom like to see data access change in the coming years? How does Tom approach the aspect of building out a team of experts in machine learning for your startup? What should founders look for? 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 Tomasz Tunguz This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Dan Adika is the Founder and CEO @ Walkme, the cloud-based service designed to help professionals guide and engage prospects and customers, and complete online tasks. They have raised over $90m in VC funding from some of the greats of the industry such as Rory O’Driscoll @ Scale Venture Partners and the team at Insight Venture Partners. As for Dan, prior to Walkme, he spent time at HP as a software engineer and before that spent 5 years in The Israeli Army’s elite computing unit. In Today’s Episode You Will Learn: How did Dan made his way from the elite computing unit of the Israeli army to San Francisco to found Walkme? What does Dan believe are the most important metrics to assess the growth and potential of a SaaS startup? What does Dan believe is a good customer payback period? What does Dan consider a good retention rate? How does Dan calculate sales rep productivity? What metric would suggest a successful rep and at what level should one be concerned? What is the KPI that Dan uses to measure customer success? When is the right time to hear your first CS rep? 60 Second SaaStr What does Dan know now that he wishes he had known at the beginning? Fave SaaS reading material? When is the right time for startups to look to acquire other startups? 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 Adika This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Brad Feld is one of the world’s leading VCs having Co-Founded Foundry Group, Brad has made investments in the likes of Zynga, Makerbot and Fitbit, just to name a few. Brad is also Co-Founder of Techstars, one of the world’s most prominent startup accelerators, whose portfolio companies have raised over $1.3bn in funding. If that wasn’t enough Brad is also a best selling author having co-authoured Venture Deals: Be Smarter Than Your Lawyer and VC and Startup Communities: Building An Entrepreneurial Ecosystem In Your Community. In Today’s Episode You Will Learn: How Brad made his way into the world of VC and came to found Foundry Group? Brad has previously stated that companies can be segmented into 3 different core components? What does he mean by this? How can startups be structured internally for scalability? Why does Brad hate the word culture? How should culture be viewed and approach internally within startups? How has Brad seen his personal development with regards to being a board member? What has he got better at? What does he believe makes a great board member? Why is CAC the easiest metric to game in SaaS? How should the CAC/LTV ratio be approached? How can entrepreneurs use this to attract VC investment? 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 Feld This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Dan Burkhart is the Founder & CEO @ Recurly, the startup powering much of the subscription success, trusted by the likes of Twitch, CBS Interactive and Hubspot just to name a few. They have raised over $20m in VC funding from leading investors including Greycroft, Freestyle, Harrison Metal and more. As for Dan, his background spans 14 years with the likes of eBay and NBC Internet in the marketing, business development and strategic partnership realm. In Today’s Episode You Will Learn: How did Dan make his way into the world of SaaS and come to found Recurly? How does Dan perceive a good CAC/LTV ratio? Does he agree with the hallowed 3:1 often cited by founders and investors? How does Dan manage and measure customer churn? How does he approach regrettable and non-regrettable customer churn? What is the post-mortem analysis of customer churn? How does Dan insert an element of accountability without creating a sense of churn? 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 Burkhart This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Scott Friend is a Managing Director @ Bain Capital Ventures where he has made investments in the likes of Jet and Rent The Runway. Scott joined Bain Capital Ventures in 2006 after selling the company he co-founded, ProfitLogic, to Oracle. At ProfitLogic, Scott saw the immense scaling of the company from its initial three founders to a 300 person global software and solutions business serving the retail industry. As a result, in 2005, Scott was named a winner of the Ernst & Young “Entrepreneur of the Year Award”. Following the acquisition, Scott was Chairman of the Executive Advisory Board and VP of Marketing and Science for Oracle Retail. In Today’s Episode You Will Learn: How did Scott make the transition from building a 300 man SaaS startup, ProfitLogic to being a VC with Bain Capital Ventures? What are the 3 fundamental ways SaaS has changed over the last decade? What does this mean for SaaS founders and investors today? What is the single most important metric for Scott when evaluating a SaaS investment opportunity? Why is this and how has that thought process changed? How can startups optimise for sales efficiency? Where does Scott see most startups make mistakes in this field? When is the right time to hire your first customer success rep? Does it have to be embedded within the founding team? How can startups look to scale this and analyse risk over time? 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 Scott Friend This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Mat Ellis is the Founder & CEO @ Cloudability, the startup that provides cloud cost efficiency at scale and they have raised close to $40m in VC funding including from our good friends at Foundry Group and Data Collective. As for Mat, prior to Cloudability, Mat held executive positions with four startups, and key technology roles at Frito-Lay, Pepsi Cola and Goldman Sachs and he currently sits on the boards of the Oregon Entrepreneurs Network and the Technology Association of Oregon. In Today’s Episode You Will Learn: How did Mat make the move from the UK to SaaS startup founder in Portland, Oregon? How has Mat seen elements change within the business when moving through the stages of company growth? What were the challenges when going through these strategic inflection points? At present, many SaaS founders are looking to hire COOs, what does Mat believe about this hire? When is the right time to make the hire? What should one look for in their first COO? How does Mat assess the balance of sustainability and growth? How does Mat balance between this tough line? What are the inherent challenges? What are Mat’s thought on culture maintenance when startup move into hypergrowth? What is core to retain this startup culture with the scaling through 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 Harry Stebbings SaaStr Mat Ellis This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Peter Gassner is the Founder & CEO @ Veeva Systems, the industry cloud for life science systems. With just $4m in capital raised, Peter has taken Veeva to almost $500m in ARR and a prominent force in the rising tide of enterprise SaaS. As for Peter, prior to Veeva, Peter was a Senior Vice President of Technology at Salesforce where he experienced the successful IPO of the company and their rise into the most successful SaaS platform in the industry. Before Salesforce, Peter was with PeopleSoft for 9 years where he led a team of 450 professionals to support PeopleSoft’s technology platform. I do also want to say a big thank you to Jason Lemkin for the intro to Peter today without which the episode would not have been possible. In Today’s Episode You Will Learn: How did Peter make the move from Salesforce to founding one of the leaders in SaaS, Veeva? Why did Peter not want to be CEO in the beginning? What was the catalyst for his changing mindset? How has view of CEOship evolved over the Veeva journey? How does Peter assess the attractiveness of a market? What are the 2 questions Peter asks before going into a market? Is it wrong to move into smaller adjacent markets? How does Peter assess the suitability of potential board members? What does he mean when he says all founders should use the ‘grocery store rule’? What is required to close 7 figure enterprise deals? How can sales teams look to build this relationship with large co’s in a natural and non-transactional way? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Daniel Ruch is the Founder and CEO @ Rocketrip, the startup that reduces travel spend by rewarding employees to save. They have backing from some incredible investors including the likes of Bessemer Venture Partners, Canaan Partners and Y Combinator. Prior to Rocketrip, Dan was a VP in Europe for Tremor Video and before that he held several director and managerial level positions at TACODA until TACODA’s sale to AOL. In Today’s Episode You Will Learn: How did Dan make his way into the world of SaaS and come to found Rocketrip? How important is accountability for the founder and CEO? How do you convey this commitment and responsibility to the team? Are there any downsides? At what stage does Dan believe the generalist transitions to the specialist? How has Dan seen his team evolve from stage to stage? What have been the challenges within each stage? How does Dan approach hiring strategy? How does he look to determine people/company fit? Dan has said before that he ‘would not hire without a track record’, why is this? How does Dan view internal budgets? What are the fundamentals to cost saving within the business? How does Dan think one can cut cost without lowering morale? 60 Second SaaStr What is Dan’s fave SaaS reading material? What does Dan know now that he wishes he had known at the beginning? Carrot or stick, what does Dan prefer to implement? 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 Ruch This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Alex Rosen is a Managing Director with IDG Ventures where he focuses on investments in cloud infrastructure, SaaS applications, ad tech, and consumer marketplaces. Alex currently serves as board director at Chubbies, Krux, MindMeld, Minted, Smartling, Tempered Networks, and Uplift. He also led IDG Ventures’ investments in multiple companies including Appboy, Datanyze, Indiegogo, Nuzzel, The League and many more incredible companies. Previously, he was a General Partner at Sprout Group, where he was head of the Internet and Software group. Huge thanks to the team @ Sapphire Ventures for the intro to Alex today. In Today’s Episode You Will Learn: How did Alex make his way into the world of SaaS investing and come to be Managing Director @ IDG? SaaS businesses can be massively affected by changes in a few very small data points. So what would you say is one of the single most important metric points? What is a booking? How should we break it down into the 3 different MRRs? What element of those metrics do you want to see growing? How important a role does unit economics play? What are the couple of forms: customer + sales person? How much ARR should a good sales rep add to in ARR in relation to comp? What is negative churn? How can you take a customer you have already sold and make more money from them? Upsell or cross-sell? What does this to the pricing axis? Why do you want more than 1 axis? 60 Second SaaStr What does Alex know now that he wishes he had known in the beginning? What are the greenfield opportunities in SaaS for Alex? What is Alex’s fave SaaS reading material? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Alex Rosen This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Nadim Hossain is the Founder and CEO @ BrightFunnel, the startup that shows marketing true impact on revenue. They are backed by many past guests of the show including Matt Garratt @ Salesforce Ventures, Tim Kopp, and James Cham @ Bloomberg Beta. As for Nadim, prior to founding BrightFunnel, Nadim was VP of Marketing and Sales Development at PowerReviews, paving the way to a $170M exit. He was also a product marketing executive at Salesforce.com during their hyper-growth years. In Today’s Episode You Will Learn: How did Nadim make his way into the world of SaaS and come to found BrightFunnel? To what extent is marketing an art or a science in today’s data driven world? How can marketers use and analyse data to drive decision making? How can founders determine which channels are a must have as opposed to a nice to have? What metrics should determine this? Does brand building not count in the revenue driven world today? Nadim has previously said, ‘marketing is eating sales’. What does Nadim mean by this? How does Nadim evaluate the expansion of the marketing funnel? What are the biggest mistakes B2B companies make in today’s environment? How can they rectify this and sustain a brand that will deliver for the long term? 60 Second SaaStr 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 Nadim Hossain This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Michael Pryor is Co-Founder & CEO @ Trello, now Head of Product with Trello at Atlassian following their recent acquisition. For those that do not know, Trello lets you work more collaboratively and get more done. Prior to the acquisition they raised from some of the best in the business including the likes of Spark Capital, Index Ventures and Box Group. Michael is also a board member at StackOverflow. In Today’s Episode You Will Learn: How did Michael make his way into the world of startups and come to found Trello? What does Michael believe is fundamental to making a market transition successfully? What were the challenges of the early market transition with Trello? What does Michael believe are the 3 key elements that make a great CEO? How does Michael approach the element of cash burn? Does Michael agree for the need of sustainability within growth? How does Michael look to continually recruit the best talent? What are the secrets to running a 60% remote workforce so efficiently? How did the Atlassian deal come about? What was the thought process behind the sales vs raise more venture funding? How did Michael broach the process with regards to transparency within the team? 60 Second SaaStr 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 Pryor This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Matin Movasatte is the Founder and CEO @ Heap. the startup that provides analytics infrastructure to automate away the annoying parts of user analytics. They have raised funding from some of the best in the business including our friends and former guests of The Twenty Minute VC including Pejman Nozad, Alexis and Garry @ Initialized, Josh Reeves at Gusto, Redpoint and more incredible investors. As for Matin, prior to Heap Matin was a product manager at Facebook and spent time at both Google and Mozilla. I would like to say a big thank you to Jason Lemkin for the intro today. In Today’s Episode You Will Learn: How did Matin make his way into the world of SaaS having been at Facebook and Google? What were Matin’s biggest takeaways from seeing how Facebook operate? What were the pros and cons of their operations? How has this influenced how he builds Heap today? Why does Matin believe that you should always sell your product before it is done being built? What benefits does this have in terms of pricing and iteration? What are the dangers of asking for payment upfront? Why does Matin think it is crucial to hire your customer success team before your sales team? How do customer success drive customer acquisition? What does Matin mean when he says that “product organisation fit” is so important? How can startups determine the fit? What can be done to optimise this? 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 Matin Movasatte This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Didier Elzinga is the Founder & CEO @ CultureAmp, the world’s most powerful employee feedback and analytics platform. They have raised funding from some of the best in the business including the likes of Index Ventures, our friends at Felicis Ventures and Blackbird Ventures. As for Didier, he previously co-founded technical academy award winning Rising Sun Research and is non-executive director at Tourism Australia, the Atlassian Foundation and Slingsby Theatre. I also have to say a huge thank you to Ilya @ Index and Niki @ Blackbird for the intro, without which the show would not have been possible. In Today’s Episode You Will Learn: How did Didier make his way into the world of SaaS? What was the a-ha moment for him with CultureAmp? What were Didier’s biggest takeaways from watching Scott and Mike build Atlassian? How did that affect and alter how he structured CultureAmp? How does Didier evaluate product market fit? What are the signs? What metrics determine whether you have it or you do not? Why did Didier decide to bootstrap until $1m ARR? Why does Didier believe there is so little innovation in the go to market strategies of today? What would he like to see change and where does he see opportunity? Why does Didier not believe in paying sales teams commission? How does this affect his ability to hire? How does this affect the internal compensation structure of the firm? 60 Second SaaStr Didier’s Fave SaaS resource? What does Didier know now that he wishes he had known at the beginning? What has been the most challenging element of the CultureAmp journey? 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 Didier Elzinga This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Fayez Mohamood is the Founder and CEO @ Bluecore, the company that is transforming the way eCommerce marketers use data and automation to communicate with customers. They have raised nearly $30m in funding from some of the best in the business and past guests of the show including the teams from FirstMark Capital and Felicis Ventures just to name a few. As a result they have enjoyed some rapid scaling having seen the team grow from 50 to over 100 in just 10 months. As for Fayez, prior to Bluecore he was Head of Product at BigDoor and before that he founded, Gameday Tycoon, a fantasy sports game that runs on Facebook. In Today’s Episode You Will Learn: How did Fayez make his way from fantasy sports game to successful SaaS founder with Bluecore? To what extent does Fayez consider B2B marketing an art or a science with the rise of data? How can SaaS startups use data to drive conversion and upsell? What metrics does Fayez hone in on? What 2 methods does Fayez use to harmonise the sales and marketing team? How can these teams be structured to ensure for a clear communication channel and culture of transparency? With the team growing from 30 to over 100, what does the hiring process look like for Fayez? How has this altered and developed over time? What have been the big lessons in the rapid scaling of the team? How does Fayez view efficiency within organisational structures? What must founders watch out for in the scaling process of their companies? 60 Second SaaStr Advantages and disadvantages of being a SaaS firm in the US? Fayez’s fave SaaS reading material? What does Fayez know now that he wishes he had known when he started? 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 Fayez Mohamood This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Aaron Levie co-founded Box with three high school friends in 2005 when they discovered there wasn’t a modern solution for sharing and collaborating on work.They created Box to provide businesses with an easy way to share, access and manage information with enterprise-grade security, compliance and governance.Eleven years later, Box has been adopted by nearly 65% of the Fortune 500 and has nearly 70,000 paying business customers. The company went public in January 2015, and remains one of the fastest growing enterprise software companies. In Today’s Episode You Will Learn: How did Aaron with 3 friends from high school come to found one of the fastest growing enterprise software companies in Box? How does Aaron view the convergence of enterprise and consumer products in the coming years? How does this convergence effect IT providers? How does Aaron view transparency within organisations? How does this affect information flow? What must CEO’s consider when contemplating transparency within their organisation? How does Aaron evaluate the inflection points in the growth of Box? What were the challenges in overcoming these hurdles? How did he have to change as a CEO to combat these changes? What does the rise of AI mean for businesses and enterprise? What does the rise of VR allow the enterprise that was not previously possible? How do these emerging technologies affect the product and strategic roadmap at Box? 60 Second SaaStr Aaron’s favourite SaaS reading material? What will it take for Box to be 10x from here? What does Aaron know now that he wishes he had known in the beginning? What does Aaron spend most his time on that he would like to change? 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 Aaron Levie This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Luke Retterath is the Director of Demand Generation @ Duo Security, the most loved company in security. They have the backing of some of the best investors in the business including Benchmark, Redpoint, Google Ventures and True Venture just to name a few. As for Luke, his role is to develop, execute, and manage demand generation programs assessing the effectiveness of all marketing programs as well as defining goals, metrics and ROI’s for the differing programs. In Today’s Episode You Will Learn: How did Luke make his way into the world of SaaS and come to found unicorn startup, Namely? What are the 3 practical tests Luke uses to assess demand gen candidates in the hiring process? What are the right questions to ask? Is it right to look for badges on the CV? Once the demand gen team is in place, how do we get the team jump started? Where should the focus be placed? What are the 5 things that have helped drive growth at Duo? How can founders implement these into their demand gen strategy to 3x revenue for 3 years? How should one plan and forecast when it comes to demand gen? How does Luke approach the topic of MQLs? How does this change for the inside sales team? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Douglas Hanna is the GM of the Developer Platform @ Zendesk, one of the world’s fastest growing SaaS startups. Before joining Zendesk, Douglas was the Founder & CEO @ Help.com where he grew the business from 1 to 16. Prior to Help, Douglas was the CEO of A Small Orange, the web hosting firm that was acquired by Endurance International Group where Douglas was on the Executive team when they went public on the NASDAQ. In Today’s Episode You Will Learn: How did Douglas make his entry into the world of SaaS and Zendesk? What were the big adjustments that Douglas had to make from founding and working in smaller companies to working at Zendesk? What is the core to making the successful move? How can companies go about building a platform? What are the fundamentals to consider once you have decided on the platform approach? What are the challenges? How can a startup measure the success of their platform? What are the benchmarks and metrics that must be observed? How does testing and iteration play a role in platform success? How does Douglas approach the go to market element with regards to platforms? How has the world of platform go to market changed in the world of omni-channel? 60 Second SaaStr Biggest mistake companies make with their platform approach? Fave SaaS reading material? What does Douglas know now that he wishes he had known at the beginning? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Douglas Hanna This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Jonathan Lehr is the Co-Founder and Managing Director of Work-Bench, where he focuses on early stage enterprise technology investments in areas including big data analytics, machine learning, data-defined security and more. Prior to Work-Bench, Jon founded the NY Enterprise Technology Meetup in January 2012 and organizes monthly meetups of the 5,000+ person group as a way to promote collaboration for the enterprise tech ecosystem in New York. Jon has also worked at Morgan Stanley on the Office of the CIO team in IT. In that capacity, he partnered with internal technology clients to facilitate the selection and on-boarding of emerging technology vendors. He has also written about enterprise technology trends for publications such as The Wall Street Journal’s CIO Journal and TechCrunch. In Today’s Episode You Will Learn: How did Jonathan make his way into the world of enterprise investing with WorkBench? Jon has previously said that enterprise tech is like chess, so what are the rules to play by? What can startups do to increase their chance of winning the game? How can startups build scalable and natural relationships with decision makers in large enterprise clients? What are the fundamentals to doing this successfully? What does this conversation look like? What does the buying decision making process look like in large corporates? How does that differ from space to space? How does that affect the sales cycle? Why is NYC the best place in the world to start an enterprise tech company? What are the pros and cons of being in NYC? 60 Second SaaStr Greenfield opportunities in enterprise technology? What does Jonathan know now that he wishes he had known at the start? Jonathan’s fave SaaS reading material? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Jonathan Lehr This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

JD Peterson is CMO of Trello where he heads the company's marketing and customer service teams. A true child of Silicon Valley, J.D. has been helping startups for nearly 20 years. Before Trello, he held positions as the CRO and interim CEO at Scripted, the VP of Marketing at Zendesk, and the VP of Products at Marketo. JD takes pride in building world-class teams, helping companies accelerate growth, and ensuring the customer remains at the center of every strategic effort. In Today’s Episode You Will Learn: How did JD make his slightly unconventional entrance into the world of SaaS? Having picked Marketo and Zendesk, what does JD assess when picking companies? Once picked, how does JD evaluate culture? How does JD measure this? How does JD approach lead qualification? How does JD measure the effectiveness of lead generation, revenue or amount of leads? How does JD unify the sales and marketing team? JD has previously said that now is ‘the best but hardest time to be a marketer’. Why is this and what is behind this thesis? What are the pros and cons of the data driven marketing world? What are the commonalities among the best marketeers? JD has seen many companies scale into hyper-growth, when does JD believe is the right time to hire and expand aggressively? What roles should be filled first? What does JD optimize for in the hiring process? When is the transition point needed to have a VP? 60 Second SaaStr Is SaaS marketing B2B or B2C? What does JD know now that he wishes he had known in the beginning? Biggest mistake companies are enacting with their current marketing plans? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr JD Peterson This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Tien Tzuo is the Founder and CEO @ Zuora, one of the fastest growing SaaS companies that has been at the forefront of the rise of subscription business models. They have funding from some of the best in the business including the likes of Benchmark, Sequoia, Redpoint and Marc Benioff, just to name a few. As for Tien, before Zuora, Tzuo was one of the 'original forces' at salesforce.com, joining as employee number 11. In his 9 years at salesforce.com, served in numerous different roles including as Chief Marketing Officer for two years, and most recently as Chief Strategy Officer. In Today’s Episode You Will Learn: How did Tien make his way from being an early employee at Salesforce to founding Zuora? What were the big takeaways for Tien from seeing the meteoric rise of Salesforce? How has that experience moulded his running and strategy with Zuora today? What does Tien see as the fundamental benefits of a subscription model? What products and services does it work best for? What are the keys to assembling this model successfully? Tien has previously referred to scaling as ‘the climb’. How does he approach this analogy What was the most challenging element of scaling for Tien? How did he overcome it? Tien has previously said that market strategy is the $100m question all founders must ask. So how does Tien approach go to market? What are the fundamentals to think when considering different go to market options? 60 Second SaaStr Biggest mentor and how the relationship came about? What does Tien know now that he wishes he had known in the beginning? Highlight of the Zuora journey so far? 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 Tien Tzuo This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Lexi Reese is the Chief Customer Experience Officer at unicorn startup, Gusto and is one of the top female executives in Silicon Valley. Lexi’s passion for serving customers was sparked by her early career in microfinance as a public policy advocate with ACCION International—giving loans to people living in poverty to start their own ventures. She later worked at Google for eight years, most recently serving as Vice President of Programmatic Sales and Strategy globally. Lexi also started the Cambridge AdWords team for Google's small business organization. Now at Gusto, Lexi ensures that Gusto is continuously going above and beyond to serve all customers. In Today’s Episode You Will Learn: How did Lexi make her way from the world of Google and Facebook to SaaS with Gusto? What were the biggest takeaways from spending 8 years at Google and seeing the immense hyper-growth there? How has Lexi applied those learnings to Gusto today? How does Lexi look to put the ‘customer first’ thesis into practice? What does this look like in reality and from day 1? How can one maintain such high levels of customer service with an ever increasing customer base? How can one insert elements of repeatability to make this easier? Question from Hunter Walk: How do you fundamentally measure customer satisfaction? What benchmarks do you calibrate against to consider success? 60 Second SaaStr What does Lexi know now that she wishes she had known in the beginning? Most challenging aspect of Lexi’s role? Question from Tien @ Zuora: How do you look to avoid the hype culture that pervades the valley? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Eric Yuan is the Founder & CEO @ Zoom, the video and web conferencing service that just last week raised $100m in venture funding from Sequoia Capital. Prior to founding Zoom, Eric was Corporate Vice President of Engineering at Cisco, where he was responsible for Cisco's collaboration software development. As one of the founding engineers and Vice President of Engineering at WebEx, Eric was the heart and soul of the WebEx product from 1997 to 2011. Eric proudly grew the WebEx team from 10 engineers to more than 800 worldwide, and contributed to revenue growth from $0 to more than $800M. Eric is a named inventor on 11 issued and 20 pending patents in real time collaboration. In Today’s Episode You Will Learn: How did Eric make his way into the world of SaaS? What was a-ha moment and founding story of WebEx? How does Eric think about building products, customer first? What does that mindset and approach look like What are the main questions to ask? What are the challenges in doing so? How should one approach growth with startups? Is growth ever in need of control? If so, what can be done to control growth? How can this be done without angering investors? Eric has said before that founders must ‘spend more and burn less’. What does he mean by this? What does that look like in reality? What should be the main focus? Does Eric agree with the notion that founders always undersell? How does Eric approach the situation of leaving money on the table? What are the challenges of doing so? 60 Second SaaStr What does Eric know now that he wishes he had known at the beginning? Eric’s Fave SaaS Reading Material? Biggest advice to SaaS founders? 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 Eric Yuan This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Jason Lemkin is the Founder and VC @ SaaStr, or more accurately put Jason is a 2x founder, 1x VC, and constant SaaS enthusiast. He led or sourced the first VC investments in many leading enterprise/SaaS start-ups, Greenhouse.io, Pipedrive, Algolia, Talkdesk, RainforestQA, Automile, and more. He is also an advisor or smaller investor in Showpad, FrontApp, Influitive, BetterWorks, and other SaaS leaders. Jason has co-founded two successful start-ups selling to the enterprise. Before SaaStr and VC investing, he was CEO and co-founder of EchoSign, the web’s most popular electronic signature service, from inception through its acquisition by Adobe Systems Inc. He then served as Vice President, Web Services at Adobe, where he oversaw the growth of EchoSign and Adobe Document Services to $50,000,000 in ARR in 2012 and $100,000,000+ ARR in 2013. Prior to EchoSign and Adobe, he co-founded one of the only successes in nanotechnology, NanoGram Devices, which was acquired for $50m just 13 months after founding. Other than SaaS he is like me, no known hobbies. In Today’s Episode You Will Learn: How did Jason make his way into the world of SaaS and come to be Founder and VC @ SaaStr? ACV: What levels of ACV and characteristics suggest potential for a unicorn? How does Jason look to help founders attain higher ACVs? Why is stay focused horrible advice with regards to increasing your ACV with differing customer demands? Does Jason believe that founders always undersell? What advice would Jason give to founders that are nervous to ask for more? What customer response would excite Jason and what would make him concerned? Jason has previously said that ‘founders have to be 110% committed to sales’. What does this mean? How does this look when assessing a founder? Should founders be happy to pay their sales hires more than them? How quickly should the payback period be on these reps? Jason has also previously said that some founders financials are ‘simply ridiculous’. What makes him say this? What financials are fundamental to have very accurately pin pointed? Why is 100% gross margin impossible? 60 Second SaaStr Why does Jason like it when startups have clients that are not in tech? What does Jason know now that he wishes he had known at the beginning? What should SaaS founders look for in their investors? Why does Jason only invest out of the SaaStr community? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Jason Lemkin is the Founder and VC @ SaaStr, or more accurately put Jason is a 2x founder, 1x VC, and constant SaaS enthusiast. He led or sourced the first VC investments in many leading enterprise/SaaS start-ups, Greenhouse.io, Pipedrive, Algolia, Talkdesk, RainforestQA, Automile, and more. He is also an advisor or smaller investor in Showpad, FrontApp, Influitive, BetterWorks, and other SaaS leaders. Jason has co-founded two successful start-ups selling to the enterprise. Before SaaStr and VC investing, he was CEO and co-founder of EchoSign, the web’s most popular electronic signature service, from inception through its acquisition by Adobe Systems Inc. He then served as Vice President, Web Services at Adobe, where he oversaw the growth of EchoSign and Adobe Document Services to $50,000,000 in ARR in 2012 and $100,000,000+ ARR in 2013. Prior to EchoSign and Adobe, he co-founded one of the only successes in nanotechnology, NanoGram Devices, which was acquired for $50m just 13 months after founding. Other than SaaS he is like me, no known hobbies. In Today’s Episode You Will Learn: How did Jason make his way into the world of SaaS and come to be Founder and VC @ SaaStr? ACV: What levels of ACV and characteristics suggest potential for a unicorn? How does Jason look to help founders attain higher ACVs? Why is stay focused horrible advice with regards to increasing your ACV with differing customer demands? Does Jason believe that founders always undersell? What advice would Jason give to founders that are nervous to ask for more? What customer response would excite Jason and what would make him concerned? Jason has previously said that ‘founders have to be 110% committed to sales’. What does this mean? How does this look when assessing a founder? Should founders be happy to pay their sales hires more than them? How quickly should the payback period be on these reps? Jason has also previously said that some founders financials are ‘simply ridiculous’. What makes him say this? What financials are fundamental to have very accurately pin pointed? Why is 100% gross margin impossible? 60 Second SaaStr Why does Jason like it when startups have clients that are not in tech? What does Jason know now that he wishes he had known at the beginning? What should SaaS founders look for in their investors? Why does Jason only invest out of the SaaStr community? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Leo Widrich is the Founder & COO @ Buffer, the Simple and powerful social media scheduling, publishing & analytics. They have raised funding from some of the best including Scott and Cyan Banister, Hubspot’s Dharmesh Shah, Hiten Shah and Eric Ries just to name a few. Now in today’s talk with Leo he breaks down his and the Buffer teams Top 10 Learnings in Growing to 10m ARR. In Today’s Episode You Will Learn: What are the 3 questions Leo asks his customers to understand them best? When is the right time to ask them? How should you follow up from this? How to experiment with weekly masterminds? How do masterminds work? When is the right time to do them? What is important to remember in entering a mastermind? How does Leo assess pricing structure? Why does he think it is important to experiment with different pricing? How do you do so without losing customers or trust? Why does Leo advise startup founders to get advice from mentors with conflicting opinions? Why is this important and how should a decision be reached? 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 Leo Widrich This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

John Barrows is essentially the Godfather of Sales. We often have VPs of Sales from tech titans on the show but who trains those VPs and sales reps to be the best in the world at sales? That is where John Barrows comes in, with clients including Dropbox, Box, Marketo, Twilio and many more, John has amassed a wealth of knowledge and experience allowing him to provide the most proactive sales tips and strategies to optimise the sales process. If you have not checked out his blog, that really is a must and can be found here. In Today’s Episode You Will Learn: How did John make his way into the world of SaaS and more specifically sales optimisation? What are the key points all reps must cover in their first calls with new leads? Why is expectation setting so crucial? Why does John believe the best client to rep relationships are those that are equal? How can reps continue to provide value with every interaction? In the case of leads going dark, how can sales reps engage with the lead to ensure conversion? What words must be avoided and how should this conversation be structured? How can sales reps perfect the balance of being direct and being rude? How important is a summary email? What is the optimal structure and how should sales reps follow up on summary emails? 60 Second SaaStr The most common question asked to John by VPs of Sales? What are the benefits of Top Down prospecting? Do execs need structure? 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 John Barrows This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Michael Driscoll is the Co-Founder and CEO @ Metamarkets, the startup that provide interactive analytics for programmatic marketing. They have raised over $38m in VC funding from our good friends at Data Collective, Founder Collective, IA Ventures and more incredible investors. As for Michael, prior to Metamarkets, he started two other companies: Dataspora, a life science analytics company (acquired by Via Science in 2011), and CustomInk.com, an early pioneer in e-commerce. Fun fact: Michael is also a founding Partner of the previously mentioned VC fund, Data Collective. In Today’s Episode You Will Learn: How did Michael make his way from data lover to Silicon Valley SaaS Founder? Why does Mike believe in the inherent value of customer focus and product focus? What are the measurable benefits of being so specialised? Why does Mike believe it is so hard to be a cost leader in software? What are the fundamental challenges? What role does open source play in this? How does Mike view the alignment of the sales and the engineering team? Is it possible to have a harmonious relationship between the two? What should SaaS startup founders look for in potential seed investors? How can they determine whether they have these qualities? What should they look at in particular? 60 Second SaaStr Mike’s fave productivity tools? What most companies are doing wrong in their approach to data science? What does Mike know now that he wishes he had known at the start? 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 Driscoll This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Auren Hoffman is best known for being the former CEO and Founder @ LiveRamp, the leading data onboarder that was acquired by Acxiom for $310m. Today’s talk focuses on the 5 core lessons Auren took from that incredible journey with LiveRamp. Auren was also an angel investor and board member at BrightRoll, prior to it’s $610m acquisition by Yahoo. Today, he is the CEO at SafeGraph, the startup that is unlocking the world’s most powerful data so that machines and humans can answer some of society’s toughest questions. In Today’s Episode You Will Learn: What is Auren’s thesis towards hiring all round athletes as opposed to position players? When do it make sense to do either? What stage of the company is right for which persona? What are the two different types of sales personas? At what type of company should you hire a relationship driven sales team and then what type of company for a product driven sales team? Why does Auren believe you should target a very small niche of the market? What are the benefits of such focus? How can you sell such a small market to VCs? How does Auren perceive the future of enterprise software? How has the rise of bottoms up sales affected the SaaS environment? How many more SaaS companies and buyers of SaaS are there today, compared to 10 years ago? 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 Auren Hoffman Algolia the robust search API that allows developers to integrate lightning fast, typo-tolerant search into their SaaS product. Out of the box, Algolia offers developers a powerful platform for building great search experiences. By owning the entire stack from engine to server, Algolia free up development teams to focus on adding intuitive search that delights users. This is perfect for existing search teams looking to spend less time on maintenance and infrastructure management and more time on user experience. For small SaaS teams, Algolia is a great investment on top of your existing stack that requires no specialist engineers. And you can learn more about how Algolia helps SaaS Scale Search and get started on their 14-day Free Trial at Algolia.com/SaaStrPodcast This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

David Hassell is the founder and CEO of 15Five, the leading web-based employee feedback and alignment solution that is transforming the way employees and managers communicate. They have backing from the likes of Matrix Partners, Point Nine Capital and many more leading investors. As for David, he was named "The Most Connected Man You Don't Know in Silicon Valley" by Forbes Magazine, David has also been featured in The New York Times, The Wall Street Journal, Inc., Entrepreneur, Wired, Fast Company, and the Financial Post. In Today’s Episode You Will Learn: How did David made his way into the world of SaaS and came to found 15Five? How does David view competition? How should founders view additional competition to their space? What is the right response? Why did David choose such a public and deliberate fight back against one competitive attempt? David has said before that is passionate about the meaning and purpose of the business vehicle. What does he mean by this? How does this affect his thinking toward management and organisational structure? What are the keys to creating a harmonized, incentivized and happy culture for your business? How scalable is this approach and how has David seen his approach alter and develop with the growth of the company? Why did David choose the more bootstrapped funding option over the traditional heavy reliance on VC funding? Which startups is this right for? How can founders know when is the right time to put the pedal to the metal? 60 Second SaaStr David’s fave productivity tools? David’s biggest mentor and how it came about? What does David know now that he wishes he had known at the start? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr David Hassell This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Alex MacCaw is the Founder & CEO @ Clearbit, the startup that is building a suite of business intelligence APIs to help companies find more information on their customers in order to increase sales and reduce fraud. They have backing from some of the best early stage investors including the likes of First Round Capital, SV Angel, Intercom’s Eoghan McCabe, Hubspot’s Dharmesh Shah and many more incredible investors. As for Alex, as well as being a fellow Brit who loves tea, he also worked at the likes of Twitter and Stripe prior to founding Clearbit. In Today’s Episode You Will Learn: How did Alex make his way into the world of SaaS and came to found Clearbit in SF having grown up in the UK? Should API driven companies have sales teams? Should they do outbound? What’s the most effective way to generate leads? Alex has said before that the trouble is, ‘everyone is treating their customers the same”. What does he mean by this? How do the smart companies differ? How possible is it to address customer specific needs at scale? How does this scalability alter when elements like freemium and self service models are added to the equation? How effective have freemium tools been for Alex as a lead gen to on board new customers? Why did Alex choose the same pricing structure as the likes of Stripe and Twilio? What was the thought process behind this? 60 Second SaaStr How important is it for SaaS startups to be in SF? What does Alex know now that he wishes he had known when he started? Biggest mentor to Alex and how it came about? Fave SaaS reading material? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Alex MacCaw This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Ryan Smith is the Founder & CEO @ Qualtrics, an online survey company with 1,200 employees and a valuation of more than $1bn. They have backing from some of the world’s best investors including the likes of Sequoia, Accel and Insight Venture Partners having raised a $150m Series B in 2014. As for Ryan, there are many awesome things, first, he has built Qualtrics from Utah allowing him to gain perspective outside of the traditional tech bubbles, second, he held off on attain VC funding for many years despite the common belief that it is necessary for unicorn growth and finally he has the most incredible work life balance I have seen and if you have not already you must check out this piece on him in Forbes, it really is a must. In Today’s Episode You Will Learn: 1.) How Ryan made his way into startups and came to found Qualtrics? 2.) Sequoia’s Bryan Schreier states that Ryan’s success is due to running the company on ‘first business principles’. What does he mean by this? How does this affect the way Ryan runs Qualtrics? 3.) Why did Ryan decide to bootstrap the company for such a long time with the likes of Accel and Sequoia looking to invest? What are the benefits of retaining such control? What are the financial requirements to do so? 4.) What makes the best CEO’s? How do they view the internal structure of the company? How do they perceive their role? How do they manage their day and optimise their time? 5.) How does Ryan look to instill ‘radical transparency’ in the organisation? What are the benefits of doing so? Can an organisation ever be too transparent? What are the challenges of such transparency? This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

David Rodnitzky is founder and CEO of 3Q Digital, a leading digital agency that was acquired by Harte Hanks in 2015. Prior to 3Q Digital, he held senior marketing roles at several Internet companies, including Rentals.com (2000-2001), FindLaw (2001-2004), Adteractive (2004-2006), and Mercantila (2007-2008). David currently serves on advisory boards for several companies, including Marin Software, MediaBoost, Mediacause, and a stealth travel start-up. In Today’s Episode You Will Learn: How did David enter the world of B2B SaaS marketing? What was the entry point for him? What really is SaaS marketing? Is it more consumer or B2B like? How does this alter and develop with the growth of the company? Before spending heavily on marketing, what gating factors should SaaS founders think heavily about before the big spend? Should this marketing plan be undertaken by an external firm or an internal team? What market channels should a SaaS company consider as ‘must haves’ in today’s world, as compared to ‘nice to have’s’? How does David differentiate between the two? We are always told if you cannot measure it, do not do it? How can SaaS companies measure the success and effect of their marketing campaigns? What are the key metrics that define success? 60 Second SaaStr Biggest mistake current SaaS companies are currently enacting with their marketing? Favourite marketing resources and tools? What does David know now that he wishes he had known at the beginning? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr David Rodnitzsky This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Steve Garrity is COO and founder of Hearsay Systems the leading advisor-client engagement solution for the financial services industry. Hearsay have backing from the likes of Sequoia, NEA, Kleiner Perkins Partner, Mike Abbott and Path Founder, Dave Morin. Before founding Hearsay, Steve worked as an engineer at Microsoft Corporation in Seattle is a graduate of Stanford University with a BS and MS in Computer Science. While at Stanford, he was selected as a Mayfield Fellow in the Stanford Technology Ventures Program. During which, he joined Fortify Software as a product manager. Steve is also an investor in, and advisor to a number of Silicon Valley start-ups. In Today’s Episode You Will Learn: How did Steve made his way into the world of SaaS from the world of Microsoft? How does Steve approach the management around his engineering team? How does Steve balance management of engineers while still allowing creativity? Are there dangers of giving engineers freedom? Is it possible to have both a happy engineering and sales? How does Steve look to harmonise the team? Is it not contra popular theory to have different cultures for different segments of the team? Why does Steve believe that executive coaching is an almost universal requirement? How does Steve justify that to the board? 60 Second SaaStr Steve’s Biggest Productivity tools? What does Steve now know that he wishes he had known at the start? The biggest mistake SaaS companies are enacting with their social media strategies? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Steve Garrity This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Peter Reinhardt is the Founder and CEO @ Segment, the startup that allows you to collect all of your customer data and send it anywhere and they count some of the biggest and best companies in the world as customers including the likes of Reuters, HotelTonight, New Relic and Atlassian. They do not only have some of the world’s leading customers but some of the world’s best investors with the likes of Accel, Thrive and Kleiner Perkins participating in their latest $27m Series B. I would like to say a huge thanks to Grant Miller @ Replicated for the intro to Peter today. In Today’s Episode You Will Learn: How did Peter make his way into the world of SaaS and come to found Segment? How does Peter define product market fit? Does he agree with Justin Kan in stating that it is when you get the first 10 customers that are unaffiliated? Why does Peter believe product market fit suffers when related to Job’s idea of the reality distortion field? What is so damaging and what should founders look to avoid? How do technical and non-technical co-founders differ in their approach to product market fit? How do their expectations, desires and reactions alter to differing levels of uptake? How did Peter navigate the process of scaling prices with time? Was he nervous when doing so? What does Peter advise founders when attempting significant price increases? 60 Second SaaStr What were the biggest takeaways from YC? What does Peter know now that he wishes he had known at the beginning? The biggest challenge in building out the team? Favourite SaaS resource or reading material? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Peter Reinhardt This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Seth Besmertnik is the Co-Founder & CEO @ Conductor, the company that boasts the biggest customer list in their category including more than 500 Fortune and Internet Retailer 500 brands like Under Armour, Citi and FedEx with their web presence management and SEO. With this incredible success, the company has been ranked 13th fastest growing software company in the US and the 3rd Best Place To Work in NYC. They have also raised funding over $60m from some of the best investors on the east coast in the form of Matrix Partners and FirstMark Capital just to name a few. I would like to say a huge thanks to Fayez @ Bluecore for the intro to Seth today. In Today’s Episode You Will Learn: How did Seth make his way into the world of SaaS? What was the a-ha moment for Conductor? What does Seth mean when he says, ‘B2B companies need to build a weapon in their marketing’? How does this look in his approach? How does this differ according to differing startup budgets? Previously, Meaghan Eisenberg @ MongoDB has said ‘the largest lift you are going to see is from your site’. Does Seth agree with this? How should we prioritise the site? What are the fundamentals to consider in terms of optimising conversion? With the proliferation of content today, to what extent should B2B companies look to alternative platforms such as Snapchat, Youtube and Instagram for content differentiation? What are the fundamentals to consider with platform diversification? How does Seth suggest creating a culture of content creation in previously segmented cultures? How can this be done with actionable strategies to encourage non-marketing professionals to produce content? 60 Second SaaStr What does Seth know now that he wishes he had known before? Biggest advice on content creation for B2B SaaS companies? Fave SaaS reading material? Being a CEO vs Being a Founder 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 Seth Besmertnik This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Kathryn Minshew is the Founder & CEO @ The Muse, named to Forbes’ 30 Under 30 in Media and Inc.’s 15 Women to Watch in Tech. Before founding The Muse, Kathryn worked on vaccines in Rwanda and Malawi with the Clinton Health Access Initiative and was previously at McKinsey. Kathryn has spoken at MIT and Harvard, appeared on The TODAY Show and CNN, and contributes on career and entrepreneurship to the Wall Street Journal and Harvard Business Review. In Today’s Episode You Will Learn: How Kathryn came to found The Muse? What was the a-ha moment for her? Why did Kathryn introduce a SaaS business model into the traditionally, transactional model of recruiting? What were the benefits and how did it alter her go to market? With no prior sales experience, how did Kathryn find the experience of running the sales team? What were the core takeaways? At what stage should the founder stop selling the product and hire a sales team? Why does Kathryn believe you have to make the customer feel slightly uncomfortable to be successful? What did Kathryn look for in her initial sales hires? Why did Kathryn hire 3 reps to start with and not 2, as usually suggested? How does Kathryn approach the customer success field at The Muse? When did Kathryn hire her first CS rep? What is Kathryn’s take on CS being involved in the sales process? 60 Second SaaStr What does Kathryn know now that she wishes she had known when she started? Biggest mistake SaaS companies are enacting with their recruiting process? Productivity tips and hacks? 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 Kathryn Minshew This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Michael Sharkey is CEO & Co-Founder of Autopilot, the startup that allows you to automate customer journeys as simply as drawing on a whiteboard. Autopilot has funding from some of the best investors both in Australia and in SaaS with backing from the likes of Salesforce Ventures and Blackbird Ventures. Prior to founding Autopilot with his two brothers, Michael joined his brother Chris to grow start-up Stayz into a top Australian rental booking site which was acquired by FairFax Digital in 2006 and again by HomeAway for $225M in 2013. Michael also co-founded digital marketing agency Sharkey Media where he helped grow Australian startups. I would love to say a huge thank you to Matt Garratt @ Salesforce Ventures for the intro to Michael today. In Today’s Episode You Will Learn: How did Michael come to co-found Autopilot with his two brothers? What was the a-ha moment for him? Why did Michael choose a self service model with Autopilot? How does this model affect their CAC? How does this model alter the outbound marketing strategy? How does Michael approach the dilemma of variable or fixed pricing? Has Michael found that the lack of reliability around variable pricing causes customers concern? With Michael interest in unit economics, why are we seeing many SaaS startups, Marketo and Eloqua, exiting with losses? What can founders do to adopt the unit economics first mindset? How does this attitude to unit economics affect attitudes to aggressive growth? Michael focuses on 100% net retention, what does that process and strategy look like in practice? How does this commitment to 100% retention affect Michael’s management style and work processes? 60 Second SaaStr Biggest mentor to Michael and how it came about? What does Michael know now that he wishes he had known in the beginning? The biggest mistakes SaaS companies make with their email marketing processes? 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 Sharkey This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Robert Siegel is a Partner at XSeed Capital, one of the leading seed funds in the valley. At XSeed, Rob specialises on, you guessed it, all things from the wonderful world of SaaS and he sits on the Board of Directors of Cape Productions and Caller Zen. Robert is currently on the faculty at the Stanford Graduate School of Business where he teaches an array of topics that he led to His role as the Co-President Emeritus of Stanford Angels & Entrepreneurs. Prior to joining XSeed, Robert was General Manager of the Video and Software Solutions division for GE Security, with annual revenues of $350 million. Before that, Robert was Co-Founder & Chief Executive Officer of Weave Innovations Inc. (acquired by Kodak). If that was not enough Robert also served in various management roles at Intel Corporation, including an executive position in their Corporate Business Development division, in which he invested capital in startups that were strategically aligned with Intel’s vision. I would also like to say a huge thanks to Tien @ Zuora for the intro to Robert today. In Today’s Episode You Will Learn: How did Robert make his way into the world of SaaS? What was it about XSeed that made him want to make the transition from operations to VC? We have seen many big SaaS exits in the last year with Marketo and Nutanix, does Robert think the time for big SaaS exits has come and gone? Have we moved to a world of consolidation? How do companies both large and small need to react to this shift on a strategic level? How does this affect the internal infrastructure of larger companies? For smaller startups, how should their attitude to competition change? How does this change Robert’s search process as an investor? How can smaller startups make themselves attractive acquisition targets? How does Rob’s view of consolidation affect his excitement for mega returns in SaaS? How does it impact how Rob approaches valuation? How does this change Rob’s expectations of unit economics? 60 Second SaaStr Strategic investors: Good or Bad? What does Rob know now that he wishes he had known when he started? Fave SaaS resource or reading material? Greenfield opportunity in SaaS? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Robert Siegel This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

David Thompson is CMO at Domo, the company that allows customers to turn data into opportunities. David is a highly accomplished branding expert and recognized leader in demand generation, having served as longtime CMO of WebEx, where he named the company, helped create the cloud-based conferencing category and positioned the company for its IPO and subsequent buyout by Cisco. He also co-founded and served as chief executive officer of Genius.com, a leading SaaS marketing automation company, and he launched the Sales 2.0 Conference. In Today’s Episode You Will Learn: How did David make his way into the world of tech and SaaS pre-bubble? How did the bubble affect how David approached company building going forward? What should all SaaS startups consider pre spending big on marketing? What should their core gating factors be? Is it always right to have an internal marketing team? What are the must haves and the nice to haves in B2B marketing? Why is Facebook a must have or business branding today? How can businesses accurately measure the success of their marketing and branding efforts? Is it all about revenue or is there external reputation metrics to consider? On the whole, would David consider successful B2B branding closer to consumer or closer to enterprise marketing? What do the best in the enterprise class do? 60 Second SaaStr What are David’s favourite marketing tools? If David could recommend one book to SaaS founders what would it be? With the martech explosion: are we entering a world of consolidation? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr David Thompson This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Daniel Saks is the Co-CEO of AppDirect, which he founded in 2009. AppDirect is the leading commerce platform for selling cloud services and at the firm, Daniel plays a key role in the growth and development of AppDirect, from attracting a leading team, to nurturing relationships with customers and partners. AppDirect has backing from some of the leading investors in the world including the likes of Foundry Group and J.P. Morgan. Prior to AppDirect, Daniel worked at Viant Capital, a boutique tech investment bank. In Today’s Episode You Will Learn: How did Daniel make the move from family business to SaaS founder? How did he get the business off the ground in the early days? From working in his family business, what did Daniel observe about the buying patterns of businesses? What makes Daniel believe humans like to buy from humans? Is it a problem that many of today’s software vendors lean on direct sales? What are the first steps to create a multi-channel approach? What does it take to support indirect sales channels such as affiliates and resellers? What is Daniel’s 4 Step Playbook for optimising the distribution of software? What does it take to move past the early adopter audience into the hands of the wider market? Why does Daniel believe that the promise of SaaS is yet to be fully realised? What excites Daniel with the rise of the cloud and the movement away from on-premise? 60 Second SaaStr When is the right time to hire your first customer success rep? What does Daniel know now that he wishes he had known at the beginning? Biggest challenge in the AppDirect journey and how Daniel overcame it? 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 Daniel Saks This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Part 2 with David Skok, now David is a serial entrepreneur turned VC at Matrix Partners. He founded four companies: Skok Systems, Corporate Software Europe, Watermark Software, and SilverStream Software and did one turnaround with Xionics. Three of the companies he founded went public and one was acquired. In 2001 David joined Matrix Partners, who had backed his last two startups, as a General Partner. David’s successful exits as an investor at Matrix include: HubSpot, JBoss, AppIQ, Tabblo, Netezza, Diligent Technologies, CloudSwitch, TribeHR, GrabCAD, OpenSpan and Enservio. David currently serves on the boards of Atomist, CloudBees, Digium, Meteor, Namely HR, Salsify, and Zaius. You can also find David’s amazing blog here! Huge thanks to Hardi Meybaum and Jason Lemkin for the intro to David today. In Today’s Episode You Will Learn: What is negative churn? Why is it fundamental for SaaS startups to have a strong grasp of their negative churn? How does negative churn affect the pricing axis? What can startups do if they have no alternative product to upsell to? To what extent should founders be willing to engage in customisation in order to upsell a product? What are the dangers? What should founders be mindful of? To what extent is up sell the responsibility of customer success? Should they have a hand in the sales process? What are the dangers and concerns? How important is it for a startup to track their champion with the customer company? Does it matter if your champion leaves? What should you do if so? 60 Second SaaStr If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr David Skok This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com