The Official SaaStr Podcast: SaaS | Founders | Investors

Jason Lemkin is the Founder @ SaaStr, the world’s largest SaaS event with over 20,000 of the world’s best SaaS founders and investors attending every year. Jason also invests from SaaStr’s debut $70m fund and has made prior investments in the likes of Algolia, TalkDesk, MixMax, Rainforest QA and many more incredible companies. In Today’s Episode You Will Learn: When is the right time to hire your first sales rep? What characteristics must those sales have? Why does Jason believe it is impossible to poach a rockstar from another fast scaling startup? Should you then hire the stretch VP or the more experienced, potentially burnt out exec? How does Jason think about aligning compensation to company objectives? Within the company, which functions serve as the best test areas for variable compensation? What must you be wary of when installing a system of variable compensation? When is a stretch VP a stretch too far? What must a stretch Head of Sales have done to make him ready? What must a VP of Product done before to make him ready? What resources can you build around stretch VPs to provide them with additional support? How does Jason think about the first time you spend to acquire customers? Why does Jason suggest just trying to make $1 for every $1 you spend? Why is it crucial to think of your marketing spend on a blended basis? How can you create alignment between the marketing teams number and the cadence of sales? 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

Jon Lee is the Founder & CEO @ ProsperWorks, the #1 recommended CRM for G Suite. To date, ProsperWorks have raised over $85m in VC funding from the likes of True Ventures, Norwest, GV, Bloomberg Beta and more incredible names. As for Jon, prior to ProsperWorks, he started in investment banking at Merrill Lynch before moving to run a large operations team at Yahoo. Jon then founded Bazaar Advertising Solutions, a business self funded from a Palo Alto apartment that Jon scaled into a highly profitable $47m business in less than 2 years. Jon then sold Bazaar to Epic Media in 2006. Following the acquisition, Jon founded DNA Games, the number one casino simulation game on Facebook with more than 20 million players, ultimately acquired by Zynga in May 2011. In Today’s Episode You Will Learn: How Jon made his way into the world of CRM having successfully founded and sold 2 prior business in the lead gen and gaming space? Why does Jon believe building a SaaS business is very much like building a gaming business? How does on think about the scaling of company culture with the scaling of headcount? Where does Jon see the inflection points where this culture starts to break down? What does Jon mean when he suggests “the importance of a culture of innovation”? Why does Jon believe it is so important to insert a culture of risk into the organisation? How does this risk mindset differ and look across different segments of the business? How does Jon aim to create a culture of risk and ambition without a fear of failure and not hitting targets? Why does Jon think it is always better to start in SMB and move to enterprise? How does this decision change how one thinks about product roadmap? How does this change how one approaches traction building ahead of fundraising? What should one look to learn from rapid iteration and testing before moving to the enterprise market? 60 Second SaaStr? What does Jon know now that he wishes he had known at the beginning? What keeps Jon up at night? What is Jon’s favourite 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 Jon Lee 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

Chetan Puttagunta is a General Partner @ NEA, one of the world’s largest venture capital firms in the world with over $3Bn in their latest fund and a portfolio including the likes of Mulesoft, Jet.com, Uber, Houzz and many more incredible companies. As for Chetan, Chetan focuses on enterprise software and has made investments in MuleSoft, MongoDB, Elastic, Heap, just to name a few. Due to his phenomenal track record, Chetan has been named to GrowthCap’s Top 40 under 40 Growth Investors, Forbes 30 under 30 All-Star Alumni List, and Forbes’ 30 under 30 in Venture Capital. In Today’s Episode You Will Learn: How Chetan made his from the world of leveraged buyouts to the world of enterprise VC investing with NEA? Why does Chetan have such conviction with regards to open source companies today? Why does he feel the big question of “Can open source product multi-billion dollar companies” has been proven”? How does Chetan think about the underlying business models of open source when comparing the likes of Red Hat with 85% gross margin to Hortonworks at negative gross margins? What does Chetan believe is a healthy ratio between professional services vs closed premium features? Does Chetan believe this is the end for per seat pricing in SaaS? How does Chetan approach market sizing today when evaluating potential enterprise opportunities? Why does Chetan believe there is a mental trap in the VC requirement for large markets? How can founders present the niche market they are attacking, in an exciting enough way to satiate the investor appetite for large market? Chatan has said before, “if you have conviction and vision, you should not be afraid to raise capital and go big”. Does every founder not have conviction and vision in the early days? How does Chetan determine when truly is the right time to pour fuel on the fire and raise that mega war chest? 60 Second SaaStr? A moment in Chetan’s life that has changed the way he thinks about the world? Fave SaaS reading material? What does Chetan 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 Chetan Puttagunta 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

Rob Reid is the Executive Vice President & Managing Director @ Sage Intacct, the undisputed global leader serving finance teams of any size. With over 10,000 employees and and over 3m customers, their financial solutions generate over $2Bn in revenue. As for Rob, prior to Sage Intacct, Rob led Intacct over an incredible 8 year journey culminating in their, reported $850m exit to Sage in 2017. Before that he was CEO and President of LucidEra, a market leader for on-demand business intelligence. Prior to LucidEra Rob was group Vice President of industry leading Siebel CRM for Oracle, managing the SMB sector. Fun fact, over his phenomenal 30 year career, Rob has been involved with 8 startups, 7 of which have had successful exits. In Today’s Episode You Will Learn: How Rob made his way into the world of SaaS over 30 years ago from wanting to be in advertising and hating computer science? As a multi-time CEO, how has Rob seen his role and understanding of what it takes to be a great CEO changed over the last 30 years? Does Rob agree that “management upscaling is the most important role a CEO can do”? What does Rob mean when he says, “the old school CEO approach is upside down and backward”? How should it be in that case? Why does Rob believe that an executive team is like a boat of oarsman? What are the fundamentals to ensuring your executive team are aligned and working in tandem? Why is transparency across the organisation fundamental to both efficiency and culture? How does Rob think about internal promotion vs external hire when it comes to the exec team? Why is Rob adamant that “cloud companies like never before have to be customer-centric”? What does this mean for thinking about optimising the structure of your organisation? How does one think about such high levels of customer success and touch points when serving the immense SMB landscape? How is this feasible? What have been Rob’s key learnings? 60 Second SaaStr? Following many successful outcomes, what is Rob’s biggest splurge to date? Why does Greg Sands call Rob “The Big Fundamental”? What does Rob know now that he wishes he had known at the beginning of his career? 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 Rob Reid 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

Kolton Andrus is the Founder & CEO @ Gremlin, the failure as a service startup finds weaknesses in your system before they cause problems. To date, they have raised over $8m in VC funding from some of the best in the business including the likes of Mike Volpi @ Index Ventures and Mike Dauber @ Amplify Partners. Prior to Gremlin, Kolton was a Chaos Engineer at Netflix improving streaming reliability and operating the Edge services. Fun fact, Kolton also designed and built Netflix’s failure injection service. Before that he improved the performance and reliability of the Amazon Retail website. At both companies he has served as a ‘Call Leader’, managing the resolution of company-wide incidents. In Today’s Episode You Will Learn: How a conversation in the hallway of a conference with a VC gave Kolton the confidence that he could leave the corporate world of Netflix and Amazon and start a startup? What were Kolton’s biggest takeaways from seeing the first hand scaling of behemoths like Amazon and Netflix? How did they fundamentally alter how he views goal setting today? How does Kolton look to achieve the balance of ambitious goal setting without the team losing motivation if they do not hit the goals? Why does Kolton believe that a decentralised workforce is merely an evolution in how we do business? What are the core fundamentals to achieving success in creating and scaling a remote workforce? What have been some of the biggest challenges in structuring the team this way? What is the single biggest tip Kolton has for other founders in ensuring high conversion rates from trials? Where do most founders go wrong with this? Today, is engineering buy in the only necessity to succeed in a bottoms up sales world? 60 Second SaaStr? What does Kolton know now that he wishes he had known at the beginning? If an investor can provide one thing, what is most important for Kolton? What are Kolton’s favourite SaaS reading materials? When is a stretch a stretch too far for a team member? 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 Kolton Andrus 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 Williams is the Founder @ SalesCollider, the organisation that helps technical founders jumpstart sales. Ryan got his start as the first sales manager at Adroll where he grew the team from 3 to 32 reps in just 8 months, a team that was responsible for ARR growing from $4m to $58m in under 2 years. Ryan then became an advisor to the early team at InVision where he coached both CEO and sales reps to close the first dozen enterprise deals. Then his last stop before founding SalesCollider was as VP of Sales at LeadGenius where he grew enterprise sales by over 400% and added clients such as Ebay, IBM and Google, just to name a few. Ryan is also an Entrepreneur in Residence @ 500 Startups and a Mentor with First Round Capital. In Today’s Episode You Will Learn: How Ryan made his way into the world of sales as first sales manager at Adroll and how that led to advising the CEO of InVision on gaining their first enterprise clients? 70% of VPs of Sales fail when they join early stage startups, why is this? How can founders know when is the right time to bring in their first VP of Sales? What can they do to maximise the chances of success when bringing them into the organisation? What is the right profile type for the first VP of Sales? What are the core foundations to assessing the strength of the VP in the interview, especially for engineering minded founders? What is the one question that Ryan loves to ask potential sales candidates? What answer does he look for? Does Ryan agree with a recent guest, “discounting is now table stakes”? Where do most early stage startups go wrong when thinking about discounts? What framework must startups utilise to analyse the right discount to offer? Why must they know the internal value they are providing to their customer in such a detailed way when discounting? 60 Second SaaStr What does Ryan know now that he wishes he had known at the beginning? SDR’s are the most important function in sales, agree or disagree? Sales rep productivity, what is good and what is bad? 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 Williams 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

Pieterjan (PJ) Bouten is the Founder & CEO @ Showpad, the world’s leading sales enablement platform that allows for the creation of amazing buyer experiences. To date they have raised over $89m in VC funding from the likes of Insight Venture Partners, Dawn Capital and Hummingbird. As for PJ, Showpad is the second company he has founded. In 2010 he co-founded the mobile development agency, In The Pocket and still serves on its board. Prior to In The Pocket, Pieterjan held senior roles at Netlog and Accenture. In Today’s Episode You Will Learn: How PJ made his way from the world of Accenture to founding the world’s leading sales enablement platform in Showpad? What was the most challenging element for PJ and Showpad in scaling from $1m-10m in ARR? How does the go-to-market change with this scaling? How does the team structure and composition alter? How does the branding and positioning change? PJ has said before that you must “reiterate value at every touchpoint”, what does he mean by this? How can one look to build a structure and framework to ensure one is effective with this? How does one scale this when serving thousands of SMBs? What were PJs biggest lessons from their experiences of discounting? What advice would PJ give to founders on when and how much to discount? How does PJ think about the use of pilots and trials? How can one ensure optimal efficiency of conversion with both methods? 60 Second SaaStr Does the role of CEO ever get easier? What does PJ know now that he wishes he had known at the beginning? What keeps PJ up at night? 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 Pieterjan Bouten 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

Clate Mask is the CEO of Infusionsoft, the leading cloud-based CRM platform for growth-minded small businesses with more than 145,000 users worldwide. Under Clate’s leadership, InfusionSoft has grown from a fledgling startup housed in a worn-down strip mall into a 550 person company, raising over $130m in VC funding in the process. If that was not enough, Clate is also an angel investor with the likes of CampusLogic, where he also sits on the board and is co-author of Conquer the Chaos: How to Grow a Successful Small Business Without Going Crazy. In Today’s Episode You Will Learn: How Clate made his way into the world of SaaS and came to found the leading CRM for small businesses? Enterprise vs SMB: Why does Clate fundamentally believe that not everyone has to move to enterprise with time? Why do so many founders believe they need to? Why is it such a preference for investors? How does the decision to remain in SMB change the future structure of the team and product roadmap? What was the hardest challenge for Clate about staying in SMB? The Metrics Stack: What is the core metric that founders must observe to analyse the state of their business? How does this core metric affect every other metric? How does Clate view the significance of payback period, what is good to him? How does sales rep productivity change when serving SMB vs enterprise? What is good sales rep productivity? Why does Clate fundamentally believe CAC/LTV is the mothership? What is it solely driven by? Partnerships 101: How can a founder know whether they have the right model and product for a partnerships model? How do partnership models change both the service and sales process of your company? What are the biggest risks to implementing a full-scale partnerships model? What have been the biggest challenges for Clate of scaling this partnerships model? 60 Second SaaStr What does Clate know now that he wishes he had known at the beginning? What is the most important element an investor can provide? A moment in Clate’s life that has changed the way he thinks and sees the world? 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 Clate Mask 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

Harry Glaser is the Founder & CEO @ Periscope Data, the startup that allows you to transform your business with the fastest, most powerful analytics platform. To date, Periscope have raised over $34m in funding from some of the very best in the business including Bessemer, SV Angel, DFJ, Susa Ventures and Data Collective, just to name a few. With this funding they now serve over 975 customers including Adobe, Flexport, Tinder, NewRelic and more. Prior to founding Periscope, Harry was a Product Manager @ Google. Fun fact about Periscope, it was voted the best small company to work for in 2017. In Today’s Episode You Will Learn: How Harry made his way from being a PM at Google to convincing his co-founder Tom to leave his comfortable corporate job in Seattle to chase the startup dream in the valley? Diverse Teams: There a a lot of all white male teams in SaaS, what should they do to create a more diverse, well-rounded team? What is the first step? What is the framework for achieving this hiring ambition? What are the biggest challenges? Where does Harry see founders most often making mistakes in building diverse teams? Data Teams: Why does Harry believe that founding teams must have data professionals within them from Day 1? Why does Harry believe this makes those startups more successful? What are the fundamental benefits? How does this data-centricity change the decision-making of the organisation? What are the core challenges in scaling this data team? Moving Upmarket: Why does Harry believe that it is better to do SMB to enterprise than enterprise to SMB? How does the product fundamentally change when addressing the enterprise market? How does the structure of the team change with the move? How does the messaging of the company alter with the move to a more enterprise focus? 60 Second SaaStr What does Harry know now that he wishes he had known at the beginning? Harry recently tweeted “you don’t choose the kind of CEO you are”, what kind of CEO are you then? A moment in Harry’s life that has served as an inflection point and changed the way he thinks? What can a founder do today to instantly make a better workplace 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 Harry Stebbings SaaStr Harry Glaser 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 Godley is the President of LeadGenius, the startup that provides the power of human intelligence with the scale of machine learning. To date they have raised $16m in funding from the likes of a16z, Initialized Capital, Scott and Cyan Banister and SV angel just to name a few. As for Mark, he most recently served as Chief Revenue Officer for HG Data and before that was VP of Market Development for ConnectandSell. If that was not enough, mark also holds advisory roles in the salestech and martech space, including Omniquo, ZenIQ.io and The Big Willow. In Today’s Episode You Will Learn: How Mark made his way into the world of SaaS over 25 years ago? How has he seen the industry change so remarkably over that time? Why does Mark believe that many startups today are created with the wrong intentions? Who is ultimately to blame for this, the founders or the investors who back them? Why does Mark believe that SaaS founders should “ignore fundraising and sign customers”? What are the unidentified consequences to Mark of taking external money? How does Mark view the function played by discounting in onboarding your first few key customers? What does Mark think of pilots? How willing should founders be to engage with unpaid pilots? How can enterprise founders solve the 2 big problems today of. A.) Standing out in the sea of enterprise startups? Gain trust from enterprise CIOs when they are still a small team with little brand or track record? What does Mark believe is the secret to selling to enterprise effectively? Why must founders be both credible and vulnerable when selling? What is the difference between helping someone buy and selling them a product? 60 Second SaaStr What does Mark know now that he wishes he had known at the beginning? Why are data vendors their own worst enemy? What would Mark like to change about the world of VC and 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 Mark Godley If you have a digital product, whether it’s mobile or web, Amplitude’s product analytics helps you understand what your users are doing, iterate and ship product faster, and drive metrics like engagement and retention. To learn how you can use analytics to build a sticky product that grows your business, get your free copy of the Product Analytics Playbook from Amplitude. This 155-page book (with worksheets) will help you develop a comprehensive retention strategy for your product — just click here to download. User education is one of the most powerful ways to increase engagement and retention at scale, yet is often put in the too hard basket. Elevio is the platform that removes this burden, empowering your users to self-serve contextually relevant help via their support widget and embeddable elements, increasing retention and engagement, while reducing support load. Elevio even tells you what content to add or fix and why based on usage trends from your users. Preventing content rot, and increasing coverage, which we all know is an ongoing challenge. You can also integrate with your existing support stack for content, access to live-chat, support tickets and more. Use elevio for continuous user education with 20% off your first year at (elev dot I O / saastr) using coupon code GOHARRY 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

Wade Foster is the Founder & CEO @ Zapier, the startup that moves information between your web apps automatically, so you can focus on your most important work. A couple of incredible achievements from Zapier, they have scaled to a phenomenal $35m in ARR, they have built a time of over 130 people, all without a central office and they have done this with just $1.2m in early stage funding from the likes of Bessemer, Y Combinator and DFJ. In Today’s Episode You Will Learn: How Wade made his way into the world of SaaS and came to found Zapier? Why does Wade believe that founders need to put in place traditional management sooner than they normally do? What should this structure look like? When is the optimal time to start considering it and then implementing it? Wade has said before that most startups should “ignore fundraising”, why does he believe this? How has bootstrapping Zapier influenced how he manages and scales the company? What lessons has he taken from VC backed founders that he has applied to the growth of Zapier? Zapier is a completely remote team, what is the secret to seamless communication and company culture when building a team to 130 with no central office? What are the core benefits? What are the fundamental challenges? 60 Second SaaStr What does Wade know now that he wishes he had known at the beginning? Why should everyone on the team do support? How does Wade look to scale himself as CEO? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Wade Foster If you have a digital product, whether it’s mobile or web, Amplitude’s product analytics helps you understand what your users are doing, iterate and ship product faster, and drive metrics like engagement and retention. To learn how you can use analytics to build a sticky product that grows your business, get your free copy of the Product Analytics Playbook from Amplitude. This 155-page book (with worksheets) will help you develop a comprehensive retention strategy for your product — just click here to download. User education is one of the most powerful ways to increase engagement and retention at scale, yet is often put in the too hard basket. Elevio is the platform that removes this burden, empowering your users to self-serve contextually relevant help via their support widget and embeddable elements, increasing retention and engagement, while reducing support load. Elevio even tells you what content to add or fix and why based on usage trends from your users. Preventing content rot, and increasing coverage, which we all know is an ongoing challenge. You can also integrate with your existing support stack for content, access to live-chat, support tickets and more. Use elevio for continuous user education with 20% off your first year at (elev dot I O / saastr) using coupon code GOHARRY 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

Olof Mathé is the Founder & CEO @ Mixmax, the startup that allows you to be a sales pro, providing powerful analytics, automation and enhancements for your outbound communication and a product that has achieved almost the impossible in SaaS, true viral growth and a $0 CAC. As for Olof, prior to Mixmax he led the team that built Inkling Habitat, now adopted by the world’s largest publishers and before that he was an entrepreneur and worked at Skype and McKinsey. In Today’s Episode You Will Learn: How Olof made his way to the bay and how he made his way into the world of SaaS with the founding of Mixmax? Why does Olof believe that customer success is the new marketing? What does this mean for the right time to hire your first customer success rep? What are the other subsequent advantages of instilling an early customer success team? Why does Olof believe that every company must have some haters? What does this suggest about your product? How should startup founders react to this? Is there a method of damage limitation with these segments Why does Olof think it is ok if they come from your core user base? With regards to growth, how important does Olof view the differing forms of metrics? How many should founders be focussed on? How does this approach affect your internal decision-making? How does it affect product roadmap? How does Olof break down the structure of Mixmax into 3 subsequent parts? Why does Olof not like employees in SF working from home? What are the drawbacks to this? What is the right way to recruit remote employees? Why is not all inbound poor quality? 60 Second SaaStr What does Olof know now that he wishes he had known at the beginning? How to cost effectively deal with inbound hiring applications? What is the least discussed but most worthy topic 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 Olof Mathé If you have a digital product, whether it’s mobile or web, Amplitude’s product analytics helps you understand what your users are doing, iterate and ship product faster, and drive metrics like engagement and retention. To learn how you can use analytics to build a sticky product that grows your business, get your free copy of the Product Analytics Playbook from Amplitude. This 155-page book (with worksheets) will help you develop a comprehensive retention strategy for your product — just click here to download. User education is one of the most powerful ways to increase engagement and retention at scale, yet is often put in the too hard basket. Elevio is the platform that removes this burden, empowering your users to self-serve contextually relevant help via their support widget and embeddable elements, increasing retention and engagement, while reducing support load. Elevio even tells you what content to add or fix and why based on usage trends from your users. Preventing content rot, and increasing coverage, which we all know is an ongoing challenge. You can also integrate with your existing support stack for content, access to live-chat, support tickets and more. Use elevio for continuous user education with 20% off your first year at (elev dot I O / saastr) using coupon code GOHARRY 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 If you have a digital product, whether it’s mobile or web, Amplitude’s product analytics helps you understand what your users are doing, iterate and ship product faster, and drive metrics like engagement and retention. To learn how you can use analytics to build a sticky product that grows your business, get your free copy of the Product Analytics Playbook from Amplitude. This 155-page book (with worksheets) will help you develop a comprehensive retention strategy for your product — just click here to download. User education is one of the most powerful ways to increase engagement and retention at scale, yet is often put in the too hard basket. Elevio is the platform that removes this burden, empowering your users to self-serve contextually relevant help via their support widget and embeddable elements, increasing retention and engagement, while reducing support load. Elevio even tells you what content to add or fix and why based on usage trends from your users. Preventing content rot, and increasing coverage, which we all know is an ongoing challenge. You can also integrate with your existing support stack for content, access to live-chat, support tickets and more. Use elevio for continuous user education with 20% off your first year at (elev dot I O / saastr) using coupon code GOHARRY 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 Mader is the CEO @ Smartsheet, the company that allows firms the best way to plan, track, automate and report on work. To date, they have raised over $105m in funding from some of the best in the business including Insight Venture Partners. Prior to Smartsheet, Mark served as senior vice president of global services for Onyx Software, leading the consulting and customer operations teams in the Americas, Europe, and Asia. Due to this success, in 2015, he was recognized as Ernst & Young Entrepreneur of the Year in Technology for the Pacific Northwest. In Today’s Episode You Will Learn: Why Mark’s being disrupted by Salesforce led to his entry into the world of SaaS and how he came to be CEO @ Smartsheet? How does Mark think that startups should approach hiring across market cycles? What have been some core lessons Mark has learnt in frothy markets and the war to win “hot talent”? How does Mark think about “paying up” for certain candidates? How flexible should startup founders be on moving their compensation bands? Why does Mark believe that too many people over index culture fit? How does Mark look to balance between raw IQ and culture fit? How does Mark look to really stress test someone’s ability to perform a role, pre-hire? Where do most startups go wrong in their early hiring processes? How does Mark think about creating a structured framework for giving employee feedback? Why do people overestimate the importance of the feedback itself? What else should they be focusing on? In terms of providing that feedback, how does Mark assess the importance of output? How does Mark look to balance the complicated elements of output vs input? Is it really all about activity? 60 Second SaaStr What does Mark know now that he wishes he had known at the beginning? Management upscaling is the most important role of CEO? When is a stretch VP a stretch too 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 Mark Mader 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

Fred Shilmover is the CEO and co-founder of InsightSquared, one of Boston’s premiere tech startups paving the way in the sales intelligence space. Throughout the InsightSquared journey, Fred has raised over $25m in VC funding from the likes of DFJ, Bessemer, Salesforce and Atlas Venture. Prior to founding InsightSquared, Fred was a corporate development associate with Salesforce Ventures and before that he held several key roles at Bessemer Venture Partners including associate and Director of IT. He is also a board member of TUGG, an organization that brings together tech entrepreneurs with social enterprises that support at-risk youth. In Today’s Episode You Will Learn: How Fred made his way into the world of SaaS, hustled his way to being a VC with Bessemer and then came to found InsightSquared from Boston? Why does Fred strongly argue that it is easier to start with SMB and move to enterprise than enterprise down? What are both the technical and personnel considerations of the decision? Why is it the product manager’s job to lose complexity as slowly as possible? Why does Fred disagree and state that CAC/LTV is not the guiding metric for SaaS startups? What are the core problems of CAC/LTV? What alternatives should founders consider as their guiding metrics? Where does Fred believe most founders go wrong when assessing their metrics? What metric keeps Fred up at night? What does Fred believe are the fundamentals to successfully building an inside sales team from scratch? What is the lowest ACV that an inside sales team can justify? How does Fred look to create a culture of accountability and responsibility without the element of fear of not hitting quota? Why does Fred go against conventional wisdom and suggest that customer success is the responsibility of the entire organisation? Why is this advantageous compared to a dedicated CS team? How does this mean both time and teams are allocated towards customer success? 60 Second SaaStr What does Fred know now that he wishes he had known at the beginning? What is the least discussed but most worthy topic in SaaS? What would Fred’s biggest advice to emerging SaaS founders be? 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 Fred Shilmover 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

Mike McDerment is co-founder and CEO of FreshBooks, the #1 cloud-based accounting software designed exclusively for service-based small business owners. Starting from his parent’s basement, Mike has grown Freshbooks to more than 10m users worldwide and raising over $75m in VC funding from the likes of Accomplice and Georgian Partners. Mike is also the co-author of Breaking the Time Barrier, downloaded more than 250,000 downloads since its release. In Today’s Episode You Will Learn: How Mike came to enter the world of SaaS with the founding of Freshbooks from his parent’s basement? Why does Mike disagree with the common notion of the “pivot”? How does Mike balance between realism when something is not working and vision? From Mike’s conversation with USV’s Fred Wilson, what does he believe are the 3 most important roles of the CEO? Why is the No 1 rule in SaaS, you do not replatform your software? What are the inherent dangers? How does it affect your ability to drive revenue? Where do most SaaS startups make big mistakes when replatforming? Where are the inflection points in SaaS team scaling? What is the biggest challenge at 20 people? How does collaboration change when your team hits 40 people? How can one maintain seamless communication when one hits 80 people? 60 Second SaaStr Why is Mike so bullish on SaaS outside of Silicon Valley? How does being outside the Valley affect his ability to hire? What does Mike 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 Mike McDerment 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

Ross Mason is the Founder & VP of Product Strategy @ MuleSoft, one of the world’s leading software platforms making it easy to connect the world’s applications, data and devices. Following over $250m in VC funding from the likes of Lightspeed, Salesforce Ventures, Sapphire Ventures and NEA, MuleSoft then went public in March 2017, popping as much as 45% on it’s first day of trading. As for Ross, prior to MuleSoft, he was CEO of SymphonySoft, an EU-based company providing services and support for large-scale integration projects. Previously, Ross was Lead Architect for RaboBank and played a key role in developing one of the first large-scale ESB implementations in 2002. In Today’s Episode You Will Learn: How Ross made his way into the world of SaaS with the founding of MuleSoft? Why did Ross decide to move full time to the West Coast having started the company in Europe? What were the biggest challenges about the move to the US? What advice would Ross give to prospective entrepreneurs, looking to make the move? Where does Europe exceed the US and vice versa? What does it really mean to be a SaaS platform? What 3 elements of a company benefit when a product unbundles into a SaaS platform? How does unbundling change the process for building products and services? How does unbundling change the ability to drive new revenue streams? How does unbundling change core operational elements of the business? What does Ross mean when he says we are shifting from verticals into value chains? Does Ross believe it is even possible to own the entire customer lifecycle today, from start to finish? 60 Second SaaStr What does Ross know now which he wishes he had known at the beginning? How did it feel the day MuleSoft went public? What advice does Ross commonly hear being given that he most disagrees with? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Ross Mason This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

David Skok is a serial entrepreneur turned VC at Matrix Partners. He founded four companies: Skok Systems, Corporate Software Europe, Watermark Software, and SilverStream Software and did one turnaround with Xionics. Three of the companies he founded went public and one was acquired. In 2001 David joined Matrix Partners, who had backed his last two startups, as a General Partner. David’s successful exits as an investor at Matrix include: HubSpot, JBoss, AppIQ, Tabblo, Netezza, Diligent Technologies, CloudSwitch, TribeHR, GrabCAD, OpenSpan and Enservio. David currently serves on the boards of Atomist, CloudBees, Digium, Meteor, Namely HR, Salsify, and Zaius. You can also find David’s amazing blog here! In Today’s Episode You Will Learn: How did David make his way into the world of SaaS? What was it about Matrix that made him want to make the transition from operations to VC? Metrics: Why are metrics so important? What role do they play in an organisation? How do good founders respond to questions on not achieving sales targets? What metrics in SaaS really determine the trajectory of the business? How can founders examine unit economics to determine whether they have a sustainable SaaS business? How does David address sales rep productivity? How much in ARR should they be booking in relation to their annual comp package? Negative Churn: 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? Upsell: 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 upsell 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? 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

Des Traynor is the Co-Founder, Chief Strategy Officer and VP of Marketing at Intercom, one of the world’s hottest startups that simply put, makes communicating with customers easy and efficient. They have raised over $115m in funding from some of the world’s leading investors including Social Capital, Index Ventures, Bessemer Venture Partners and then titans of industry with Mark Zuckerberg, Jack Dorsey and the Collison brothers at Stripe. Prior to Intercom, Des previously co-founded Exceptional (now a part of Rackspace), and prior was a UX designer for web applications. In Today’s Episode You Will Learn: How Des made his way from founding consultancy web design businesses in Ireland to founding SaaS superstar, Intercom, with Eoghan and moving to San Francisco? Why does Des believe that “brand is the most overlooked element for new startups”? How must founders think differently when constructing their brand for a single product vs multi-product company? What is the right way to think about this brand architecture? How involved should customers be in the development of product roadmap? Where are the nuances and challenges to this? When is the right time to start thinking about releasing a second product? What is the right and the wrong way for this to be marketed? What does Des mean when he says, “there is an inverse correlation between quality and market size”? How should founders think about selling to both SMB and enterprise? How do their buying psychology and implementation process differ? 60 Second SaaStr When I say success, who is the first person that comes to Des’ mind? Where do most startups go wrong with their branding? What does Des 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 Des Traynor 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

Greg Sands is the Founder & Managing Partner @ Costanoa Ventures, one of the leading early stage enterprise funds on the West Coast with their latest $175m fund, raised earlier this year. At Costanoa, Greg has made investments in the likes of Intacct (acquired by Sage for $800m), Quizlet, DemandBase and previous guest, Grovo, just to name a few. Prior to founding Costanoa, Greg was a Managing Director at Sutter Hill, where he was an early investor in the likes of Feedburner, AllBusiness, and Return Path. Before Sutter Hill, Greg was on the other side of the table as the first hire at Netscape after its founding engineering team. As Netscape’s 1st Product Manager, Greg wrote the initial business plan, coined the name Netscape, and created the SuiteSpot Business Unit, which he grew from zero to $150m in revenue. He also served as Manager of Business Development at Cisco where he architected a global channel management plan. In Today’s Episode You Will Learn: How did Greg make his way into the world of SaaS as the first non-engineering hire at Netscape and then make his way into the world of SaaS investing, subsequently? Why does Greg completely disagree with the hailed notion of, “The Rule of 40”? Why does Greg believe it has achieved such status and recognition in market today? Where are the large nuances? If not the rule of 40, what metrics and benchmarks should early stage SaaS founders be focussing on? If we disregard “The Rule of 40”, how does that impact the emphasis that should be placed on profitability? Tom Tunguz stated on the show, ““growth is the largest determinant of value at IPO, not profitability”. What are Greg’s thoughts on this? In that scaling process, Greg has said to me before, “the first hire in every function should be a Swiss army knife hire and most people go wrong”. What does Greg mean when he says a Swiss Army Knife, how does that change in marketing vs sales? Where do most people go wrong within this? How does Greg define the different phases of product market fit? Why does Greg advocate that all founders approach product market fit with a “crawl, walk, run” approach? What examples does Greg have where this has worked and what specifically about this allowed it to work so well? 60 Second SaaStr Logos or expansion? Pros and cons of usage based pricing? What does Greg know now that he wishes he had known in 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 Greg Sands 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

Spenser Skates is the Founder & CEO @ Amplitude, the only analytics solution built for modern product teams that helps you understand user behaviour and ship the right solutions fast. They have raised over 55m in VC funding from many friends of SaaStr and 20VC including Eric Vishria @ Benchmark, Neeraj Agrawal @ Battery Ventures, the teams at IVP, Data Collective, Box Group and SV angel, just to name a few of their incredible investors. Prior to Amplitude, Spenser founded Sonalight, an app that allowed users to text while they drive, backed by the likes of Y Combinator. In Today’s Episode You Will Learn: How did Spenser make his way into the world of SaaS and come to found Amplitude? How did Spenser look to build and scale his sales team, as an engineering focussed founder? Where does Spenser see most engineering founders go wrong in their approach to sales? What were the stumbling blocks that Spenser found hard in this learning process? What is his biggest advice to technical founders to scale the learning curve fast? How does Spenser view the importance of a customer’s willingness to pay? Does that suggest a correlated amount of value? How should this propensity to pay, change with the stage of the provider? How does Spenser suggest founders mitigate discounting? What have been Spenser’s core learnings in creating an incentivised sales team? What are the core drivers that yield the behaviour desired? How does Spenser look to align this with engineering teams, traditionally disgruntled with sales’ compensation packages? 60 Second SaaStr What does Spenser know now that he wishes he had known at the beginning of Amplitude? What is Spenser’s fave SaaS reading material? How does that vary according to stage of business? How does Spenser view discounting? 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 Spenser Skates 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

Lars Nilsson is the VP of Global Inside Sales for Cloudera and with over twenty-five years of sales and operations experience, Lars Nilsson is a global leader in enterprise software and selling solutions. One of Lars many incredible achievements was he and his team at Cloudera built the sales methodology Account-Based Sales Development (ABSD), which has transformed how businesses approach high-value targets. Prior to Cloudera, Lars founded SalesSource, a business services consulting firm specializing in CRM customization and sales process development. Lars has also served in sales executive roles at ArcSight/Hewlett Packard, Riverbed Technology and Portal Software – all three of which achieved IPOs, in addition to Cloudera (2017). As Special Advisor at True Ventures, Lars helps True portfolio companies develop sales compensation plans from the ground up, implement best-of-breed sales technologies, and rapidly scale sales teams to meet demand. In Today’s Episode You Will Learn: How did Lars make his way into the world of enterprise sales back in 1995? How has Lars seen the industry change so significantly over the last 22 years? Why does Lars believe that SDRs are the most important role in sales? How does their role of ensuring a full pipe compare to the role of demand gen and marketing? How does Lars think about setting a quota that ensures a desired behaviour beyond pure revenue chasing? What is his framework for setting and optimising the right quota? Why does Lars believe that ales is all about activities? What activities is Lars most eager to measure and test? What is Lars’ biggest advice to someone looking to build out their SDR team from the ground up? What core characteristics should one look for in those initial SDR hires? What is and has been Lars’ biggest challenge in building out his SDR team? Why is building SDR teams in the bay so hard? How does Lars think about setting ideal customer profiles? How big a TAM is large enough to be excited, yet narrow enough to be achievable and solve a true and inherent customer need? 60 Second SaaStr What does Lars know now that he wishes he had known at the beginning? What is Lars favourite piece of SaaS reading material? Sales rep productivity, what does Lars believe is the scale from exceptional to poor? 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 Lars Nilsson 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

Jyoti Bansal is the former Founder & CEO @ AppDynamics, backed by the likes of Lightspeed, Greylock and Kleiner Perkins just to name a few before it’s ultimate acquisition by Cisco for $3.7Bn. Today, Jyoti is the Founder and CEO @ BIG Labs essentially a laboratory for creating, developing and launching innovative ideas. The first of these ideas being turned into companies being, Harness.io the industry’s first continuous delivery as a service platform, where Jyoti is the Founder & CEO. As a result of his tremendous success, Jyoti has been a recipient of many leadership awards including, "Best Cloud Computing CEO to Work For", "Best CEO" by San Francisco Business Times. In Today’s Episode You Will Learn: How Jyoti made his way from selling agricultural machinery with his father in India to creating one of the fastest growing enterprise companies with AppDynamics? $0-3m ARR: What is the key goal and objective for startups scaling through this phase? How can startups look to accurately determine what their North Star in this stage? To what extent should the founder involve the customer in product roadmap and development? $10-15m ARR: What are the core objectives for the business in this stage of the cycle? How should founders view competition through this phase? What does Jyoti mean when he says about “go-to-market strategy fit”? How can this be determined most accurately? $60-80m: What should be front and centre of the mind of the entrepreneur at this stage? Why does Jyoti believe it is here that it is crucial to get sales execution right? WHere are the breaking points that occur in the team scaling at this phase? How does the role CEO change here? Pre-IPO: Why is operational efficiency so crucial in this stage of the business? What did AppDynamics do best at this stage of the business? Where would Jyoti say AppDynamics could have done better in the progression through this stage? 60 Second SaaStr What does Jyoti know now that he wishes he had known at the beginning of Appdynamics? What is Jyoti’s must read SaaS material? Payback period is the most important 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 Jyoti Bansal 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

Paul Albright is one of the valley’s most experienced SaaS execs with extensive operational and capital management experience, including 3 IPOs. Most recently Paul was the Founder & CEO @ Captora, the marketing acceleration software solution that raised over $25m in VC funding from the likes of NEA and Bain Capital Ventures. Prior to Captora, Paul was Chief Revenue Officer at Marketo where he drove the overall revenue strategy across sales and marketing that delivered global revenue growth over 100% year-over-year, from $14m to $58m. In a similar position at SuccessFactors, he grew revenues to more than $200m and over 80% year-over-year growth. Previously, Paul led worldwide marketing at NetApp and at Informatica, which he joined pre-revenue through their successful IPO. If that was not enough he has also served as an entrepreneur-in-residence at Greylock. In Today’s Episode You Will Learn: How Paul made his way into the world with the likes of SuccessFactors and Marketo? What were his big lessons from seeing both companies scale into hyper-growth mode? Does Paul agree with Dave Kellogg in stating, “CAC/LTV is the single most important metric for SaaS startups? What other metrics must all VPs of Demand Gen and Sales be watching constantly? What does an efficient sales and marketing engine look like? What are the core components to build that? What are the requirements to both run this engine and scale it quickly? How does the growth of this engine affect hiring in other parts of the business? Why does Paul believe that it is much harder to go SMB up than enterprise down? What are the changes that are required on both ends? For this in “no man’s land of pricing” what does an efficient sales process timeline look like from lead to conversion? 60 Second SaaStr How does Paul think about picking the investors he works with? Is customisation always wrong? What is “good sales rep productivity” to Paul? What does Paul 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 Paul Albright 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

Jack Altman is the Founder & CEO of Lattice, the #1 performance management solution for growing companies.They have raised close to $10m in funding from some of our favourites in industry including the likes of Miles Grimshaw @ Thrive, Khosla Ventures, Elad Gil, Alexis Ohanian and YC’s Daniel Gross. Prior to founding Lattice, Jack was the Head of Business Development @ Teespring where he saw the firm move into hyper scaling. Jack has also build an incredible angel portfolio including the likes of Gusto, OpenDoor, Instacart, Zenefits and Soylent. In Today’s Episode You Will Learn: How Jack made his way from seeing the hypergrowth of Teespring to starting Lattice? What does Jack identify as the 2 core challenges to rapid scaling in SaaS? Does Jack agree with Chris Caren in stating you have to hire for 3-4 years ahead of the role? How does Jack see the role and structure of communication change with the scaling of a firm? How did the early days of selling look with Lattice? How did Jack incorporate the team into his learnings and development within the world of SaaS? What should founders look for in the first sales hire? How does that profile change with the scaling? Why does Jack believe that each and every department should have their own North Star as well as a company North Star? Does Jack concur with Eric Ries’ believe that every department must also have their own budget? In terms of metrics, how does Jack prioritise within the metric stack? What is most important for Jack to focus on? How has Jack seen this change with time? Does Jack agree with Shan Sinha @ Highfive that it is “always about payback”? 60 Second SaaStr Jack’s Favourite SaaS reading material? What does Jack know now that he wishes he had known at the beginning? How much time does Jack spend talking to customers? 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 Jack Altman 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

Rajeev Batra is a Partner at Mayfield, a firm that has championed bold entrepreneurs since 1969. Rajeev’s investments at Mayfield include the likes of Crunchbase, SmartRecruiters, Marketo (IPO then taken private by Vista Equity), ServiceMax (acquired by GE Digital) and more incredible companies. Prior to Mayfield, Rajeev was at Mobius (Softbank) Venture Capital and Austin Ventures. Before making the move into VC, Rajeev was on the operational side as an entrepreneur and executive with three of the companies he worked with going public and later being acquired, including the very notable Siebel Systems. In Today’s Episode You Will Learn: How Rajeev made the transition from successful operator with 3 IPOs under his belt to investing in the next generation of enterprise companies with Mayfield? What does Rajeev mean when he says “startups do not die of starvation, they die of indigestion”? How does this realisation affect Rajeev’s approach to customer profiling and segmenting customers? Why does Rajeev believe that “early product market fit can be misleading”? How does Rajeev look to provide context and action from numbers and analytics in the early days? How does Rajeev feel that founders should approach gross margin from the early days? How should this relationship and thought process towards gross margin change over time? Why does Rajeev believe that retention is the number 1 metric for SaaS founders to focus on? In the stack of metrics, how does this compare to gross margin, CAC/LTV and payback period? 60 Second SaaStr Enterprise investing is spreadsheet investing: True or false? How does Mayfield use an internal budget to align themselves to entrepreneurs? What does Rajeev mean when he says “I look for 2 act opportunities”? 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 Rajeev Batra 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

Shan Sinha is the Founder & CEO @ Highfive, the startup that quite simply makes insanely simple video conferencing. They have raised over $45m in funding from some of the best in the business including a16z, Lightspeed General Catalyst and Founder Collective and then individuals including Aaron Levie, Drew Houston and Marc Benioff. Prior to Highfive, Shan was the Group Product Manager for Google Apps for Enterprise, which he joined following Google’s 2010 acquisition of his prior company, DocVerse, which later became part of Google Drive. In Today’s Episode You Will Learn: How Shan made his way from being one of the foundations of Google Drive to changing the world of video conferencing with Highfive? As a successful second time founder, how has Shan’s thesis around customer success changed? When is the right time to hire your first CS personnel? What profile should those first CS hires have? How does this vary to differing profiles in the scaling journey? Logos or expansion? What does Shan believe is crucial in the early days of SaaS scaling? What metric is the true determinant of whether a customer is attaining consistent value from your product? Why does Shan believe that not everything has to scale from Day 1? What are the benefits of implementing a model that is unable to scale? What does this show and teach the startup? How does Shan think about capturing the perfect customer experience? Why does Shan believe that payback period is the single most important metric for SaaS startups? How does Shan think about payback and margins when selling to the traditionally smaller ACV marker of SMB? What are the challenges in doing so? 60 Second SaaStr When is a stretch VP a stretch too far? What does Shan know now that he wishes had known when he started Highfive? Challenges of doing both hardware and software simultaneously? 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 Shan Sinha 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

Chris Caren is the CEO @ Turnitin, the company revolutionising the experience of writing to learn with backing from the likes of IVP, Norwest Venture Partners and GIC. Chris has scaled the company to serve over 25m students and 2m teachers across 15,000 institutions. Prior to joining Turnitin in 2009, Chris spent 4 years with Microsoft as a General Manager and before that 3 years at Business Objects as a VP of Product Marketing. In Today’s Episode You Will Learn: How Chris made his way into the world of SaaS and came to be CEO @ Turnitin? What were Chris’ biggest takeaways from watching both Business Objects and Microsoft as they scaled into hyper growth mode? What were his big lessons in management from Bernard Liautaud? What marketing takeaways did he have from working with Dave Kellogg? Why does Chris believe management team upgrade is the most important role a CEO can perform? What are the core characteristics that upgrade candidates must have for them to be an attractive hire? What culture must be built into the fibre of the leadership team? How does Chris look to manage internal discontent when bringing in external managers? How does Chris look to involve internal candidates for the role in the search for their next boss? What are the benefits of this? When is a stretch VP a stretch too far? What are the signs of potential strain? How does the team convey this? Once identified, what is the right post-mortem chain to take place? 60 Second SaaStr What should founders consider before selling their company? What does Chris know now that he wishes he had known at the beginning? What is Chris’ favourite SaaS reading material 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 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

Greg Schott is the Chairman and CEO @ Mulesoft, provider of the leading platform for building application networks. They have raised over $250m in funding from some of the best investors in the world including NEA and Lightspeed and then some of the largest companies of the day in Cisco, Salesforce and SAP. Greg joined Mulesoft in 2009 when the company only had 20 employees, over the last 8 years Greg has scaled the team to over 1,000 today in 18 countries. A real software industry veteran with over 20 years of experience building and leading high growth technology companies from early stage through IPO. In Today’s Episode You Will Learn: How Greg made his way into the world of SaaS and came to be CEO @ Mulesoft? Greg has seen Mulesoft scale from 20 to 1,000 employees today, what have been the biggest challenges in scaling the team? Where are the breaking points? What are the signs of those impending breaking points? How does that show through the team behaviour? Where do most companies go wrong in the hiring process? What is the right and wrong way to respond when a bad hire has been made? How long is long enough to determine whether a bad hire is a bad hire? Does Greg agree with the hire fast, fire fast thesis? If Greg could go back to 2009 when he joined the firm with 20 employees, what would Greg change about the way he approached hiring? What hiring advice would Greg give to an early stage SaaS company? How does Greg think about scaling sales teams? How does Greg view specialisation in the scaling of sales? When is the right time? What should CEO’s look for in their sales leaders? How does that alter at different points in the journey? 60 Second SaaStr How have things changed since IPO? When is the right time to expand product line and enter new segments? Biggest challenge with Mulesoft today? Which SaaS CEO does Greg most admire 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 Greg Schott 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

Andy Byrne is the Co-Founder & CEO @ Clari, the startup that helps sales teams drive more revenue and increase forecast accuracy through improved deal execution and predictive analysis. They have raised over $30m in venture funding from some of the best in the business including Sequoia and Bain Capital Ventures. Prior to Clari, Andy was part of the founding executive team at Clearwell Systems—Gartner's highest ranking e-discovery company—which he helped grow from pre-product & pre-revenue in 2005 to $100 million run rate until its acquisition by Symantec (SYMC) in Q2 2011. Prior to joining Clearwell, Andy co-founded Timestock, Inc., acquired by Computer Associates (CA) via the acquisition of Wily Technology. In Today’s Episode You Will Learn: How Andy made his way into the world of SaaS and came to found Clari? What were the key takeaways from his two prior successful founding experiences? Why is it important for startups to look larger than life to potential “whale” customer? What is the methodology that startups can use to gain this appearance? What role does the website play in this? Why is it important for startups to understand the risk the buyer is undertaking at large corporates when becoming a customer? How does this mean that startups should convey the product roadmap? How can startups sell the product vision and the instant value add simultaneously? How can startups look to “create theatre” with their product? What does this really mean? How can startups do this when the product is in MVP stage? Why is it so important for the startup to make the switch from vendor to partner? How can startups use execution time as the key way to achieve this? 60 Second SaaStr What hires does Andy wish he had made earlier with Clari? Recruiting in the valley, how hard and top tips? What is the most challenging element in the day to day running of Clari? 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 Andy Byrne This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Ben Uretsky is the Co-Founder & CEO @ Digital Ocean. Under Ben’s leadership, DigitalOcean has risen from a cloud startup for developers to the second largest and fastest growing cloud computing platform. To date, more than 1m developers have deployed more than 50 million cloud servers, and the company has expanded its worldwide infrastructure footprint with multiple datacenter locations around the globe. The company has raised $123 million in funding from Andreessen Horowitz, Access Industries, IA Ventures, CrunchFund, and Techstars. Prior to DigitalOcean, he co-founded and built a managed hosting provider that supported some of the top websites online and generated million-dollar annual revenues. In Today’s Episode You Will Learn: How Ben made the move from co-founding a bootstrapped startup competing with Rackspace to co-founding DigitalOcean and competing with Amazon? What have been Ben’s big learnings in raising $123m for DigitalOcean? How does Ben suggest building a trusted relationship with VCs? How have DigitalOcean scaled to over 1m customers without a sales team? What are the core tenets that have made this possible? How does the team prioritise customer acquisition channels at DigitalOcean? How does Ben say is the right way to build a community? Sean Rad has said before the hardest part is scaling with the firm. How has been seen his scaling as CEO with the firm? How has his personal relationship to the company changed with the scaling? Hear an inflection point in the scaling of DigitalOcean and how Ben’s leadership changed as a result? 60 Second SaaStr What hire des Ben wish he had made earlier? What does Ben know now that he wishes he had known earlier? What are the key inflection points in SaaS businesses? 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 Uretsky This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Dave Kellogg is the CEO @ Host Analytics, the leader in cloud-based enterprise performance management (EPM). Previously, Dave was SVP/GM of Service Cloud at Salesforce and CEO at unstructured big data provider MarkLogic. Before that, Dave was CMO at Business Objects for nearly a decade as the company grew from $30M to over $1B. Dave has also worked in various capacities with the likes of Breeze, GainSight, Tableau and MongoDB and previously sat on the boards of ag tech leader, Granular (acq by DuPont for $300M) and big data leader Aster Data (acquired by Teradata for $325M). In Today’s Episode You Will Learn: How Dave made his way into the world of SaaS with Salesforce, came to be CMO at Business Objects and now running his own SaaS company as CEO at Host Analytics? What does David believe is the single most important metric in SaaS? How should SaaS companies structure the first four lines of their financial statements? Why is retention and renewal not always an accurate sign of customer satisfaction? How does Dave look to analyse churn? What is the post-mortem? What is more important, logos or expansion? If a startup’s churn is too high, what is the top 3 things they should do? Why must you have a “standard taxonomy” for churn? How can you construct this? How does David think about taking existing customer and up-selling them? How does he view this in contrast to cross-sell? Does Dave agree with David Skok on the need for more than 1 variable pricing mechanism? Why does Dave not encourage usage based pricing? How does Dave analyse the benefits of multi-year contracts paid upfront? How does this distort TCV and inflate the figures? Does upfront payment misalign the provider and the consumer, in terms of care and support? With that in mind, how does David view billing frequency? Contract durations? 60 Second SaaStr What does Dave know now which he wishes he had known at the beginning? What is the 90 day rule? Why is it important? How much ARR should a good sales rep add in relation to comp? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Dave Kellogg 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

Scot Chisholm is the Founder & CEO @ Classy, the world's leading fundraising platform for nonprofit organizations As a result they have raised close to $50m in VC funding from the likes of Salesforce Ventures, our friends at BullPen Capital, Mithril Capital and many more great investors. With support and funding like this, since 2011, Classy has helped more than 3,000 nonprofits and social enterprises raise hundreds of millions of dollars and be named to "The World's Most Innovative Companies in Social Good" and to the "100 Brilliant Companies" by Entrepreneur Magazine. As for Scot, he is also a prolific angel investor, investing out of a fund called Mixture that includes investments in Change.org, inDinero, Iodine, Casetext and more. In Today’s Episode You Will Learn: How Scot made his way into the world of SaaS and how a “pub crawl” came to be the founding story for Classy? What have been the key learnings for Scot in raising $50m for Classy, in an industry that is maybe not so sexy for investors? Why did Scot choose to raise both the seed and A round from angels? What advice would Scot give to aspiring founders, looking to raise? How has Scot seen the evolution of his sales team? What are the key inflection points in the scaling when elements tend to break? How important is it to segment the sales team? When should this be done? At what speed is optimal? How does Scot evaluate startups looking to move upmarket? How does the decision to move upmarket change the internal decision-making with regards to product roadmap and strategy? How does it change the role of CEO in the organisation? How does Scot look to balance the attainment of short term objectives with holding the vision for the future? How far is too far to plan ahead? How should founders think about investing in areas of the business ahead of time? 60 Second SaaStr What does Scot know now that he wishes he had known when he started? Challenges as a first time CEO/entrepreneur? The key challenges of building a SaaS company in San Diego? 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 Scot Chisholm 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 Organ, Founder & CEO at Influitive. Influitive helps B2B companies mobilize their army of advocates for more rapid and profitable revenue growth. They have raised close to $50m in VC funding from some of the best in the business including the likes of Lightspeed, First Round Capital, prior guest Cindy Padnos @ Illuminate and Nick Mehta @ Gainsight, just to name a few. Prior to Influitive, Mark was the founding CEO of Eloqua, growing the business to over 150 people, hundreds of clients and a major presence around the world in 7 years. Eloqua was eventually bought by Oracle in 2012 for a reported $810m. In Today’s Episode You Will Learn: How Mark made his way into the world of SaaS, came to found Eloqua and then what the catalyst was for the founding of Influitive? How did Mark make the decision to make profitability a goal? How did Mark communicate his desire to focus on profitability and unit economics over aggressive growth to his investors? What type of SaaS startups should consider this route more? To what extent is “landing whales” crucial to getting to cash flow positive? What are some of Mark’s big learnings in how to attain those “whales”, having done it so successfully before with Eloqua? Where do most founders go wrong and how should they approach pricing whales? Why does Mark believe paying sales reps on signing misaligns incentives? Why does he believe it is optimal to pay half on signing and half on cash being received? How do you communicate that to your sales team? To what extent should SaaS startups consider debt financing as a respectable and appropriate form of company financing? What type and stage of SaaS company does debt make perfect sense for? When is it wrong in the lifecycle to take debt? 60 Second SaaStr What hire does Mark wish he had made earlier? What does Mark know now that he wishes he had known at the beginning? Pros and cons of running a SaaS startup not in Silicon 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 Mark Organ 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

Mike Dauber is a General Partner @ Amplify Partners, the fund that backs technical founders, building technical products for technical buyers. Their portfolio consists of the likes of DataDog, Fastly, Engagio and many more incredible companies. As for Mike, prior to joining Amplify he spent more than six years at Battery Ventures, where he lead early-stage enterprise investments on the West Coast. While at Battery, he was on the Boards of Cask, Duetto, Interana, and Platfora (acquired WDAY). Mike also lead Battery’s investment in Vera, which is also in Amplify’s portfolio. He also previously invested in Splunk (SPLK) and RelateIQ (acquired CRM). As a result of this success, Mike was named to Forbes’ Midas Brink List in 2014. In Today’s Episode You Will Learn: How Mike made his way into the world of early stage enterprise investing with Battery and came to be a GP with Amplify? What does Mike mean when he says he looks for “practitioner founders”? What are the benefits of these types of founders? Why do they find product market fit faster? Does this tunnel vision not sometimes mean a lack of naivete, which can be good? Why does Mike believe that hiring sales people is like being thirsty? How can founders discover the optimal cadence for expanding the sales team? Why must founders differentiate between customers and money? Why does Mike believe that everyone needs to find their Hobbesian advisor? What characteristics should this person have? How can you find this advisor? What should their incentives be? Why does Mike believe that founders need to set the hook for VCs in the first meeting? How does this compare to how founders traditionally pitch? What should they look for in those early VC meetings? 60 Second SaaStr Why does Mike disagree with deal attribution in VC? Cyber investing: Should you invest if not a domain expert? Is enterprise investing spreadsheet investing? 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 Mike Dauber 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

Vineet Jain is the Founder & CEO @ Egnyte, the startup that delivers smart content collaboration in the cloud or on-premises. They have raised over $60m in VC funding from the likes of Kleiner Perkins, Google Ventures and one of our favourites here, Mike Maples @ Floodgate. Prior to Egnyte, Vineet founded and successfully built Valdero, a supply chain software solution provider, funded by KPCB, MDV and Trinity Ventures. Before that, Vineet held a variety of senior operational positions at KPMG and Bechtel. In Today’s Episode You Will Learn: How Vineet made his way into the world of SaaS and came to found his second startup in Egnyte? Vineet states that it is not all about top line growth, how does he look to satiate VC appetitie for growth with this mentality? Why does he think that we should discuss EBITDA margins more often within business models in Silicon Valley? Considering this conservative approach, how does Vineet determine when is the right time to put the “pedal to the metal” and raise a large round of funding and really look to gain the market? What metrics suggest product market fit to this extent? Why does Vineet argue that land and expand is all wrong? What alternative does Vineet offer for those looking to sell to enterprise? How does Vineet evaluate “The Rule of 40% For A Healthy SaaS Company”? What are the inherent flaws in this model? How can this model be gamed by posting enormous growth figures? What figures should startups input into this ratio? 60 Second SaaStr What does Vineet know now that he wishes he had known earlier? How long is long enough to give someone who is not performing? What hire does Vineet wish he had made earlier? 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 Vineet Jain 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

Max Yoder is the Founder & CEO @ Lessonly, the modern learning software used by teams to translate important work knowledge into Lessons that accelerate productivity. They have raised funding from the likes of former ExactTarget CMO Tim Kopp, OpenView Ventures and New York Times Bestseller Jay Baer just to name a few of the impressive figures involved. Fun tact; they are based in Indianapolis and so Max brings a fantastic perspective on scaling and operating a growing SaaS business outside Silicon Valley. In Today’s Episode You Will Learn: How Max made his way into the world of startups and came to found Lessonly, one of the hottest SaaS startups outside of Silicon Valley? Max has previously stated that ‘SaaS scaling happens in 3 stages’. What are those stages? What is the most challenging stage? How does the CEO need to transition with each stage? How does Max view the scaling of the team? Why does Max think it is bad to give large and often inflated titles in the early days? How can CEOs most effectively look to place people in the right place to ensure the most productive of scaling? What does Max most look for in potential Lessonly employees? Why is it so fundamental that candidates have experienced some form of professional hardship before? How does Max view the role of the board in the scaling of a SaaS organisation? What are the components that make the best boards? What are the components that make the best board members? 60 Second SaaStr What one hire does Max wish he had made sooner? What SaaS reading material can Max not live without? Pros and Cons of running a SaaS startup outside 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 Max Yoder 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

Stacey Epstein is the CEO @ Zinc, the secure communications platform for workers in front of customers, not computers. They have backing from some of the best in SaaS investing including the likes of Jason Green @ Emergence, CRV with George Zachary and GE Ventures. Prior to Zinc, Stacey was CMO at Banjo. Before Banjo, Stacey was CMO at ServiceMax where she helped fuel 5 consecutive years of triple-digit growth. Finally, before ServiceMax, Stacey was the Vice President of Global Marketing Communications at SuccessFactors. During her tenure with SuccessFactors, Stacey pioneered the marketing function in 2005, and was instrumental in the company’s successful IPO in 2007, which led to a $3.4B acquisition by SAP in 2010. In Today’s Episode You Will Learn: How Stacey made her way from Executive Assistant working for another Executive Assistant before moving to CMO and today as CEO? What were the fundamental lessons Stacey took from her career as CMO to now being CEO/ What were some of the hardest elements of the transition? What role should the CEO play in the marketing strategy and execution? What do CEO’s most often get wrong about CMO’s?What is the optimal and most efficient working relationship between CEO and CMO? How does Stacey create alignment and strong and successful communication between the traditionally conflicting sales and marketing? How does transparency help drive better business results? How can one look to instill these values and communication standards on inherited organisations they they did not found? Are there any drawbacks to transparency and communication? 60 Second SaaStr What hires does Stacey wish she had made earlier? What can females do to master the art of negotiating? Recruiting in the valley today, how tough and top tips? When is the right time to hire your CMO? 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 Stacey Epstein 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 the Founder & CEO @ Safegraph, the startup that is unlocking the world’s most powerful data so that machines and humans can answer society's toughest questions. They have backing from likes of Naval Ravikant and prior guests of the show including SignalFire, IDG Ventures and David Rodnitzky just to name a few. Prior to Safegraph, Auren has an astonishing 5 successful exits under his belt with one being, LiveRamp (sold to Acxiom for $310m in 2014). If that was not enough, Auren is also a prolific angel investor with a portfolio including the likes of ThumbTack, Rainforest QA, Brightroll and Groupon. In Today’s Episode You Will Learn: How Auren made his way into the world of SaaS and came to found his 6th SaaS startup in Safegraph? Auren has said before there are two types of successful sales people, what are these two types and what are their character profiles? What type of company should have each different profile? How does each profile interact differently with the rest of the company? Why does Auren take the contrarian view and saying that highering your price is not always the right answer? In what markets is it right to higher or lower your price? When is it the wrong time? What percentage of revenue should sales and marketing be at a healthy SaaS startup? Why does Auren believe that you can actually grow faster by having fewer employees? In what situation and start does this work and when does it not? ? Why does Auren believe that the CEO should never delegate HR? What does Auren mean when he says the best HR professionals are real capital allocators? 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 Auren Hoffman 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

Promise Phelon is the CEO @ TapInfluence, bringing the first ever influencer marketing platform to the Fortune 1000. Under Promise’s leadership the company has enjoyed a 300% increase in revenue in 2015 alone, they made the successful transition from a services to a SaaS model and were successful in raising a fantastic $14m Series B. Prior to TapInfluence, Promise was the Founder and CEO at 2 startups, one of which, The Phelon Group, grew to 8 figure revenues and was successfully acquired in 2009. Before that, Promise got her start at BEA systems. In Today’s Episode You Will Learn: How Promise made her way into the world of SaaS and came to be at BEA systems, one of the most exciting companies in the valley at the time? How does Promise view the importance of building long lasting relationships with colleagues? How does Promise suggest is the right way to leave a job and sustain the best communication and relationship with former employers and colleagues? What does Promise mean when she states the importance of upward empathy? What are the benefits of installing this in your organisation? What is the right way to breed a culture of upward empathy? How does Promise differentiate between ‘advocate’ and ‘mentor’? What is the right way to attain each of these? At what point in one’s career is the right time to have each of these? What does Promise believe is the formula for making the successful transition from a services based business to a SaaS business? How can one make the change without significant customer churn and revenue loss? 60 Second SaaStr What does Promise know now that she wishes she had known at the beginning? How does motivating people differ when outside of the valley? Should customer success be able to upsell? 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 Promise Phelon 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

Ashu Garg is a General Partner @ Foundation Capital whose portfolio includes the likes of Uber, Lending Club, Adroll and Netflix, just to name a few. As for Ashu, at Foundation he has led investments and naming just a few of them here, in the likes of Conviva, Localytics and TubeMogul, later going public in 2014. Prior to Foundation, Ashu was the General Manager for Microsoft’s online advertising business. In Today’s Episode You Will Learn: How Ashu made his way from completing to the Rubik's cube as a kid in 25 seconds to being a leading SaaS VC? How does Ashu really define scaling a SaaS company? What does product market fit really look like with regards to ARR growth? What are the 3 fundamentals that SaaS founders have to nail if they are to scale to $30m+ ARR? Why does Ashu believe it is so important to have a single insertion point? What does this mean for SaaS founders? What does Ashu advise first time founders making their first foray into the world of SaaS? How should they think about obtaining and building an ecosystem of mentors? How should they manage weaknesses within their own skill sets? Does Ashu believe with Aaron Levie @ Box, “anyone can learn to be a great CEO”? Where do technical founders most often struggle? What can be done to help them go from 0-1 on customer acquisition? Where do business led founders most often struggle? How must they think of the engineering element as a core part of the founding team? 60 Second SaaStr What does Ashu know now that he wishes he had known at the beginning? Chats: Fad in the enterprise or here to stay? Biggest inflection points and breaking points in SaaS company growth? 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 Ashu Garg 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

Kurt Bilafer is the CRO @ WePay, the most complete payments solution for platforms. To date, they have raised close to $75m in VC funding from some of the best in the business including Max Levchin and August Capital just to name a few. As for Kurt himself, prior to WePay he has had experience both in startups and large corporations with his founding of Pilot Software, sold to SAP in 2007, where he spent a further 7 years holding titles such as a Global Vice President of Sales and Director of Strategic Accounts. In Today’s Episode You Will Learn: How did Kurt make his way into the world of SaaS? What were Kurt’s big takeaways from seeing the internal machinations of SAP? What is the one metric that guides Kurt’s thinking? How can you calculate your “magic number” for your business? Why must SaaS founders switch from activity based metrics to KPI’s? How does Kurt assess scalability and repeatability of revenues? What is a reasonable ratio for sales and marketing expense to revenue? Why should SaaS founders focus on the LPI of “time to money”. How can they look to optimize this? How has Kurt seen the enterprise sales cycles change since his time with SAP? How does Kurt assess conflict within the sales and marketing teams and customer success and product teams? How can managers look to implement an element of prioritization into what sales teams submit to product teams? 60 Second SaaStr What does Kurt know now that he wishes he had known at the beginning? What is the worst piece of SaaS advice that Kurt commonly hears being given out? What should one look for in their VP of Sales? What mistake does Kurt see most in the world of SaaS? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Kurt Bilafer 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

Jens Nylander is the Founder and CEO @ Automile, the startup that makes fleet and asset management much much easier. They have backing from some of the best in the business including Godfather of SaaS himself Jason Lemkin, the wonderful team at Point Nine, Justin Kan and Dawn Capital in London. As for Jens, he really is a serial entrepreneur with past endeavours including creating Sweden’s largest music player and founding Jays, the manufacturer and developer of innovative headphones that went public and is listed on the NASDAQ. In Today’s Episode You Will Learn: How did Jens make his way into the world of SaaS and come to found Automile? How does Jens look to build a repeatable scalable sales process with Automile? What are the core infrastructure requirements needed to make the process as automated as possible? How does Jens evaluate selling into the SMB market? How does Jens look to optimise the onboarding process to maximise conversion? How does Jens look to minimise churn with a market as potentially unstable as SMB’s? Why does Jens prefer technology minded sales teams? What benefits do they bring in terms of process to the sales cycle? What should founders look for in potential new engineering led sales teams? Jens is increasing transparent, posting numerous figures on Twitter, what are the benefits of such transparency? How does that help the team to achieve the wider goal? Are there any cases, such as fundraising or exits, where transparency has negative consequences? 60 Second SaaStr What was the hardest element of leaving Europe to go big in the US? What does Jens know now that he wishes he had known at the beginning? What hires does Jens wish he had made earlier? 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 Jens Nylander 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 Loughlin is a Partner @ Accel in San Francisco, one of the leading funds with prior investments in the likes of Facebook, Dropbox, Atlassian, Slack and many more incredible companies. Prior to Accel, Steve was the CEO and co-founder of RelateIQ, later named SalesforceIQ following the acquisition of the company by Salesforce in 2014 for $390 million. Steve was also president and CEO of Affinity Circles, a professional social network that connected more than 18 million professionals. Steve has also advised or invested in the likes of Palantir Technologies, Addepar, and Roam Analytics. In Today’s Episode You Will Learn: How Steve made his way into the world of SaaS with the founding of RelateIQ and then came to be a Partner at Accel on the other side of the table? Why does Steve believe the hardest balance a founder has to consider is the balance between building for the future and building for the present? How can this short to long term dichotomy be considered effectively by the team? RelateIQ was early to the AI/ML landscape, what does Steve think they did so right with RelateIQ? Does Steve agree that for an enterprise ML play to be interesting it must fundamentally change the go to market strategy? What were the key learnings from working so closely with Marc Benioff on the Salesforce exec team? What is it about the internal structure and operations of Salesforce that make it the massively profitable behemoth that it is today? Having been a founder himself and now a VC, how does Steve look to help founders specifically? Where has Steve found that early stage founders need the most help? Where do VCs proclaim to help the most but really do not at all? 60 Second SaaStr What is the worst advice Steve often hears being given? What is something that Steve has changed his mind radically on over the last few years? What is Steve’s favourite SaaS reading material? What does Steve 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 Steve Loughlin 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

May Habib is the Founder & CEO @ Qordoba, the best platform for building truly localized products across apps, websites and marketing content. It is the fastest, most scalable way to grow from one market to many. We do also want to say a big congratulations to May for recently raising a fantastic Series with the likes of Upfront Ventures and Rincon Partners leading the round. Prior to founding Qordoba, May was Director of M&A at Mubadala and an investment banker at Lehmann Brothers and Barclays in New York. May has also been named to the 30 Under 30 and CEO of the Year award. In Today’s Episode You Will Learn: How May made her way from North Lebanon to founding one of the hottest early stage SaaS companies on the West Coast? May has quadrupled her MRR growth since last year through ‘turning her SDR’s into the smartest people in the space’. What does this mean? How can this be done and replicated? What “SDR best practices did May follow that damaged her? May has a unique approach to scaling prospect search, how does this play out Does May agree with Mark Suster with regards to always calling high on customer outbound? Why does May think there is only value in outbound to seriously qualified leads? Why does May believe that startups are wrong to think that they have to start at SMB and then move up to enterprise? How can startups immediately start with enterprise? What advice does May have in terms of asking for those big ACV’s as a small startup? What advice did May receive during her fundraising that she found particularly jarring? What other than funds does May believe fundraising can be particularly good for? 60 Second SaaStr What does May know now that she wishes she had known at the beginning? What is May’s favourite SaaS reading material? Hardest moment in the journey with Qordoba? 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 May Habib 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

Nicolas Dessaigne is the Founder & CEO @ Algolia, the most reliable platform for building search into your business. Just last week they raised $53m in funding led by Accel with participation from Jason Lemkin @ SaaStr, Point Nine Capital, AppDynamic’s Jyoti Bansal, Intercom’s Des Traynor and InVision’s Clark Valberg and more incredible investors. In Today’s Episode You Will Learn: How Nicolas made his way to YC and came to found Algolia? What are the key things that change when you cross the 10m in ARR milestone? What have been the fundamental learnings in the march to $10m in ARR? Jason Lemkin has said before that ‘the first 10 unaffiliated customers you get is the first sign of pre-success’. Does Nicolas agree with him here? When are the first signs of pre-success for Nicolas? Does Nicolas agree with Jason that $1m-$2m in ARR is always the hardest for a scaling SaaS startup? Which element did Nicolas find most challenging? How has Nicolas seen himself change and develop as a leader with these inflection points? What are the fundamental to building a successful developer community? What have Algolia done to do this so successfully? What mistakes do other startups normally make in their pursuit of this? 60 Second SaaStr What hires does Nicolas wish he had made earlier? What does success look like for Nicolas with Algolia? What does Nicolas 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 Nicolas Dessaigne 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 Carson is the Founder & CEO @ Treehouse the startup that teaches you to code and learn the skills needed to launch a new career. They have backing from some of the best investors in the business including the likes of Social Capital, Greylock Partners and then notable individuals such as Reid Hoffman, Josh Elman and Mark Suster just to name a few. As for Ryan, prior to Treehouse he was the creator of famous The Future of Web Apps Conference, showing his unparalleled access to the top tier of West Coast founders. Due to the success of the conference, Ryan later sold the event to another events company. In Today’s Episode You Will Learn: How Ryan made his way into the world of startups and came to found Treehouse? How does Ryan think all founders can build a truly diversified pipeline for developer talent? How does Ryan detect the seeds of potential in young engineers? How does he nurture them to grow and fit the desired role? How does Ryan approach regrettable and non-regrettable churn? What is the dunning process? Why is it so important to instantly increase retention and reduce churn? Does Ryan agree with Jason Lemkin that the hardest element of SaaS scaling is the $1-2m phase? Does Ryan agree with Jason in suggesting that your first 10 unaffiliated customers is the first sign of product market fit? Ryan has previously said, ‘as a founder, there is one thing you need, otherwise you will quit’. What is the one thing? Why is it so important? 60 Second SaaStr Why does Ryan know now that he wishes he had known when he started? What is Ryan’s favourite SaaS reading material? Freemium in SaaS: What are the pros and cons? 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 Carson 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

Jeetu Patel is Senior Vice President of Platform and Chief Strategy Officer of Box where he leads the Box Platform organization, driving the strategy of the platform business and developer relations. He also oversees the corporate strategy and development organization for Box. Before joining the company, Patel was General Manager and Chief Executive of EMC's Syncplicity business unit. Prior to EMC, Patel was president of Doculabs, a research and advisory firm focused on collaboration and content management across a range of industries. In Today’s Episode You Will Learn: How Jeetu made his way into the world of SaaS and came to be one of the key executives at Box? What are Jeetu’s 3 tips to startup founders looking to build high performing teams? Why does Jeetu believe that team sizes must always remain small? What are the inflection points in team size when dynamics change? What does Jeetu argue that founders must pursue really hard problems? What are the benefits of this when hiring new people to the team? How does Jeetu balance between visionary hard problems and unrealistic? What does Jeetu mean when he says, ‘do things that do not scale so you can do things that sustainably scale? What are some examples of how this has been done effectively? Where do most startups go wrong in scaling sustainably? 60 Second SaaStr What does Jeetu believe that most around him do not? Fave SaaS reading material? Why businesses will find the rules of the future very different to the rules of the past? 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 Jeetu Patel 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

Laura Bilazarian is the Founder & CEO @ Teamable, the startup that allows you to recruit the best talent from your network. They have raised funding from some stellar investors including the likes of True Ventures and SaaStr. As for Laura, she started out her career on Wall St before making forays into the world of Vietnamese hotel building and being a National Rugby Champion. Laura has also spent time with the likes of Fairmount Partners where she worked on dozens of M&A transactions to large public companies. In Today’s Episode You Will Learn: How did Laura make her way from Wall St to rugby captain to founder of SaaS startup, Teamable? Why does Laura believe that “you should always be premium”? What are the benefits to this? How does this affect how Laura views both freemium versions of products and free trials? Why does Laura believe that you have to “create an outbound sales culture as early as possible”? Why is this? Does this change according to the differing customer profiles? How can SaaS businesses aid in the closing of their clients? What can they do to make this process as seamless and easy as possible? What are the requirements for this process? Why does Laura believe there are only ‘2 ways to hire’? What are those 2 ways? What methods of inbound applications must be ignored? How can founders ensure continued quality when hiring at scale? 60 Second SaaStr What does Laura know now that she wishes she had known at the beginning? What is Laura’s fave SaaS reading materials? Competitive advantages of being a female CEO? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Laura Bilazarian 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 Suster is Managing Partner at Upfront Ventures which he joined in 2007, having previously worked with Upfront for nearly 8 years as a two-time entrepreneur. Before joining Upfront Mark was Vice President, Product Management at Salesforce.com following its acquisition of Koral, where Mark was Founder and CEO. Prior to Koral, Mark was Founder and CEO of BuildOnline, a European SaaS company that was acquired by SWORD Group. Mark is also the writer of one of my favourite VC blogs, Both Sides Of The Table which is a centre piece to the whole VC community and is a must read for all interested in entrepreneurship and VC. In Today’s Episode You Will Learn: How Mark made his way into the world of startups and came to invest in SaaS with Upfront today? What are 4 reasons why startups should prioritise professional services in the early days? Why do most VCs disagree with this? How did Salesforce do this right in their period of hyper-growth? How should early stage startups approach the topic of pricing? How can they evaluate whether to call high or low? What are the pros and cons of doing both? Mark has previously discussed the importance of finding your champion in the buying process. How can startups determine whether your champion is a decision-maker? What questions can you ask to find this out? What changes as a SaaS business scales? What are the key inflection points of company development? How does Mark view the amount B2B startups are raising today? How does Mark evaluate responsible and right spend? 60 Second SaaStr What should your first sales reps be really good at? How has Mark seen early stage SaaS startups go wrong most often? IPO markets, frothy or fantastic? What does Mark know now that he wishes he had known before? 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 Mark Suster 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