The Official SaaStr Podcast: SaaS | Founders | Investors

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

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

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

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

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

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

Jason VandeBoom, Founder and CEO of ActiveCampaign, shares insights on his journey from a small business to a leading SaaS platform. He strongly believes in starting with SMBs, explaining how it fosters better product feedback and team dynamics. VandeBoom discusses the right timing for hiring a VP of Sales and why funding isn’t always necessary for team scaling. He emphasizes the importance of customer engagement and maintaining a product-first mindset, debunking myths about pricing models and funding in the SaaS landscape.

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

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

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