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? Read the full transcript on our blog. If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr

Jon 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? Read the full transcript on our blog. If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Jon Lee

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? Read the full transcript on our blog. If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Chetan Puttagunta

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? Read the full transcript on our blog. If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Rob Reid

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

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

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

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

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

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