Jason M. Lemkin 🦄
The Official SaaStr Podcast: SaaS | Founders | Investors
The Official SaaStr AI Podcast. How to scale with the best in AI + B2B. cloud.substack.com
Author
Jason M. Lemkin 🦄
Category
Podcast website
Latest episode
Jul 10, 2026
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Episodes
SaaStr 203: Why Every Startup Should Bootstrap At Some Stage, Why Transparency In Pricing Is Not Always Optimal & Why We Have To Embrace That Service Is An Essential Part of SaaS Today with Krish Subramanian, Founder & CEO @ Chargebee 03.12.2018 29:11
Krish Subramanian is the Founder & CEO @ Chargebee , the startup that lets you go beyond billing, payments and recurring invoices — to delivering subscription experiences that "wow". To date, Chargebee have “wowed” some of the world’s leading VCs to the tune of $24m including the likes of Insight Venture Partners, Tiger Global and Accel Partners. As for Krish, under Krish’s leadership the team has...
SaaStr 202: Intercom COO Karen Peacock on Lessons Learned Running A $2.2Bn Line of Business at Intuit, The Most Important Metric You Probably Aren't Tracking & Why, When and How To Hire Your COO 26.11.2018 36:57
Karen Peacock is the COO @ Intercom, the company that provides a new and better way to acquire, engage and retain customers. To date, Intercom have raised over $240m in VC funding from some of the very best in VC including GV, Kleiner Perkins, Bessemer, ICONIQ and then individuals such as Mark Zuckerberg, John Collison, Biz Stone and Andy McLoughlin. As for Karen, prior to Intercom, she spent an i...
SaaStr 201: How To Prioritise Your Sales Pipeline, Why You Should Spend Your Time on the 10% Least Likely Leads & Why The Secret To Success In Sales Is "Calls Between The Calls" with Hannah Willson, VP Sales @ Rainforest QA 19.11.2018 28:03
Hannah Willson is the VP of Sales @ Rainforest QA , the on-demand QA solution that allows companies to discover problems that affect the customer experience before the code hits production. To date, Rainforest have raised over $40m in funding from some of the very best in SaaS including the legendary Byron Deeter @ Bessemer, Jason Lemkin @ SaaStr, Marc Benioff himself, Andreesen Horowitz and YC. A...
SaaStr 200: Should SaaS Startups Start At SMB and Scale To Enterprise or Vice Versa, What It Takes To Make The Transition From CTO To CEO & The Right Way To Think About SaaS Pricing Today With Brad Birnbaum, Founder & CEO @ Kustomer 12.11.2018 34:45
Brad Birnbaum is the Founder & CEO @ Kustomer , the first intelligent platform for customer experience that enables you to know everything about every customer. To date Brad has raised over $38m in funding for Kustomer from some of the very best in the SaaS business including Tomasz Tunguz @ Redpoint, Ed Sim @ Boldstart, Canaan Partners, Box Group and Social Leverage just to name a few. Previously...
SaaStr 199: Betterment Founder, Jon Stein on The 3 Key Roles For A SaaS CEO, How To Retain Startup Culture As You Scale Past Startup Stage & The Most Telling Questions In Candidate Interviews To Stress Test Culture-Fit 05.11.2018 27:26
Jon Stein is the Founder & CEO @ Betterment , the online financial advisor built for people who refuse to settle for average investing. To date, Jon has raised $275m in VC funding with Betterment from the likes of Bessemer Ventures Partners, Menlo Ventures, Kinnevik and Francisco Partners, just to name a few. Prior to founding Betterment, Jon spent 4 years as a consultant at First Manhattan Consul...
SaaStr 198: Decision-Making in B2B Marketing; Instinct or Data-Driven, How To Create True Alignment Between Sales and Marketing & Why Sometimes You Have To Throw The Marketing Playbook Out The Window with Maria Pergolino, CMO @ Anaplan 29.10.2018 33:42
Maria Pergolino is the CMO @ Anaplan , the company that allows you to accelerate decision-making with effective planning. To date, Anaplan have raised over $299m in funding from the likes of Meritech, Salesforce Ventures, Shasta, DFJ Growth and more incredible names. As for Maria, prior to Anaplan, Maria was Senior Vice President of Global Marketing and Sales Development at Apttus, where she direc...
SaaStr 197: Partnerships: When Is The Right Time, What is The Right Partnership, How To Determine Between An Individual That Can Scale with The Company vs One That Cannot & How To Make Fast Decisions When You Don't Have Data To Lean on with Cristina Cordo 22.10.2018 33:31
Cristina Cordova leads the Payments Partnerships and Platform Partnerships teams at Stripe , the new standard in online payments that handles billions of dollars of business every year for forward thinking businesses around the world. To date, Stripe has raised over $680m in funding from some of the very best in the business including Sequoia, Founders Fund, General Catalyst, Thrive, CapitalG, Kle...
SaaStr 196: Stripe COO Claire Hughes Johnson on How The Best Leaders Inspire with Confidence and Stability, The Key To Successful Decision-Making & How To Hire Quality Teams At Scale 15.10.2018 30:02
Claire Hughes Johnson is the COO @ Stripe , the new standard in online payments that handles billions of dollars of business every year for forward-thinking businesses around the world. To date, Stripe has raised over $680m in funding from some of the very best in the business including Sequoia, Founders Fund, General Catalyst, Thrive, CapitalG, Kleiner Perkins and Tiger Global. As for Claire, pri...
SaaStr 195: How To Truly Understand The Politics of Selling to Enterprise, Why Current Org Charts Are Upside Down and What Your Customer Success Team Has To Be Obsessed with Doing with Dan Reich, Founder & CEO @ Troops.ai 01.10.2018 30:16
Dan Reich is the Founder & CEO @ Troops.ai , the startup that is the ultimate slackbot for sales teams. To date, Dan has raised over $17m in VC funding with Troops from many friends of the show including Felicis Ventures, Founder Collective, First Round, Nextview, Susa Ventures and even Slack. As for Dan, he is also the Co-Founder and President of TULA , a private equity backed health and beauty b...
SaaStr 194: ARR Is A Lagging Not A Leading Indicator, The Metrics You Need to Focus On, The Secret To Success In Selling To Developers, Why You Should Delay The Buildout of Customer Success Teams & How Small Numbers In SaaS Can Deceive You with Steve Newm 24.09.2018 32:27
Steve Newman is the Founder & CEO @ Scalyr , the startup that helps your devops team solve more problems in less time with log monitoring and analysis in seconds. Steve has raised over $27.5m in funding with Scalyr from many friends of the show including Susa Ventures, Bloomberg Beta, Shasta and GV. As for Steve, prior to Scalyr, he was the Founder of Writely which was acquired by Google to become...
SaaStr 193: When Does ABM Make Sense and How To Execute The Strategy Effectively, Why Marketing Must Be Held Accountable To A Number Tied Directly To Revenue and What Makes The Truly Special CMOs with Joe Chernov, CMO @ Robin Powered 17.09.2018 32:29
Joe Chernov is the Chief Marketing Officer at Robin , the startup that simplifies scheduling, visibility and management of meeting rooms, desks and people in your workplace. To date, Robin have raised over £9m in funding from some of our dear friends in the form of BoldStart, Accomplice and FirstMark, just to name a few. As for Joe, prior to Robin he was the CMO @ Insight Squared where he led the...
SaaStr 192: Why Multi-Year Deals Are Not All Good, What Whatever Funding You Think You Will Need Double It & The Challenges of Building A Company and A Category Simultaneously with Michael Katz @ mParticle 10.09.2018 29:51
Michael Katz is the Founder & CEO @ mParticle , the customer data platform that integrates all of your data and orchestrates it across channels, partners and systems. To date, Michael has raised over $75m in funding with mParticle from the likes of Social Capital, Greylock Partner, GV, Battery Ventures and more great names. Prior to founding mParticle, Mike was the Founder & CEO @ Interclick, wher...
SaaStr 191: Salesloft Founder Kyle Porter on Scaling A SaaS Business to $40m ARR Outside of Silicon Valley, Pivoting a Product Generating $7m in ARR & How To Fundamentally Create Cohesion In A Leadership Team 04.09.2018 32:14
Kyle Porter is the Founder & CEO @ Salesloft, the leading sales engagement platform delivering a better sales experience. To date, Salesloft have raised over $75m in funding from some of the best in the business including Emergence, Insight Venture Partners, Techstars and even LinkedIn. As for Kyle, he has led the team from 4 employees in 2014 to over 320 today where they have also been awarded At...
SaaStr 190: Why SaaS Founders Should Not Sell Their Products in The Early Days, How Founders Can Build Relationships with Enterprise CIOs and The Right Way To Think About Discounting and Pilots with Ed Sim, Founding Partner @ Boldstart Ventures 27.08.2018 31:32
Ed Sim is the Founder & General Partner @ Boldstart Ventures , one of the leading players in early stage SaaS investing. Their MO, to be a first check VC for enterprise founders and they have backed the likes of GoToMeeting (acq by Citrix), LivePerson (IPO, NASDAQ), Divide (acq by Google), Kustomer, Snyk and BigID just to name a few. Ed is also a cofounder of MState , a growth lab for enterprise b...
SaaStr 189: When to Go Large on Go-To-Market, How To Scale Company Culture with Your Team & Why Discounting is Evidence of Not Communicating Your USPs Successfully with Craig Walker, Founder & CEO @ Dialpad 20.08.2018 28:28
Craig Walker is the Founder & CEO @ Dialpad , the startup that provides a business phone system for the modern workplace. To date, Craig has raised over $120m in VC funding with Dialpad from some of the best in the business including Iconiq, Andreesen Horowitz, Google Ventures, Felicis and Bill Marris’s Section 32. Prior to Dialpad, Craig was an EiR @ Google Ventures and founded and product manage...
SaaStr 188: Why The Best CEOs Are Inspirational A******s, How To Optimise Decision-Making within Your Organisation & The Benefits of Being Old In SaaS with Fouad ElNaggar, Founder & CEO @ Sapho 13.08.2018 40:38
Fouad ElNaggar is the Founder & CEO @ Sapho , the only employee experience portal designed for the digital workforce. To date, Ray has raised over $27m in funding with Sapho from some real favourites of ours including Ray @ Caffeinated, Felicis, Uncork, Bloomberg Beta, Clark Landry and Howard Lindzon @ Social Leverage, just to name a few. Prior to founding Sapho, Fouad was the Chief Strategy Offic...
SaaStr 187: Point Nine's Christoph Janz on Making Venture Capital More Human, WTF Really Is Product Market Fit & The Leading Indicators of Scaling and Repeatable Customer Acquisition Channels 06.08.2018 37:42
Christoph Janz is the Managing Partner @ Point Nine Capital , one of Europe’s leading early stage funds with a portfolio that includes the likes of ZenDesk, Algolia, Delivery Hero, Revolut, Contentful and many more incredible companies. Before that, he co-founded two Internet startups ( DealPilot.com in 1997 and Pageflakes in 2005). In 2008 he became an angel investor and discovered Zendesk, Clio,...
SaaStr 186: From Greylock To $1.55Bn Acquisition, Adaptive Insights CEO, Tom Bogan on How The Best CEOs Hire and Retain Their Best Talent, How To Think About Gross Margin with Scale & The One Metric All SaaS Founders Must Ultimately Focus On 30.07.2018 30:37
Tom Bogan is the CEO of Adaptive Insights , the company that proves a new generation of business planning software for finance and beyond. Prior to their reported $1.55Bn acquisition to WorkDay, Adaptive Insights raised over $175m in VC funding from the likes of Bessemer, Salesforce Ventures, Norwest Venture Partners and many more incredible investors. Prior to Adaptive Insights, Tom was a partner...
SaaStr 185: Moat CEO, Jonah Goodhart on How To Scale A Logo Machine In the Early Days & Why Brand and North Star Should Drive All Decision Making 23.07.2018 33:58
Jonah Goodhart is the CEO @ Moat , the SaaS analytics and intelligence company focused on transforming brand advertising online. Prior to their acquisition by Oracle for a reported $850m Moat raised over $67m in VC funding from the likes of Insight Venture Partners, Founders Fund, Mayfield, Founder Collective, SV Angel and more incredible names. Prior to founding Moat, Jonah was the founding inves...
SaaStr 184: Step by Step Guide To Scaling Your Sales Team, Why Founders Need To Spend More Time On Top of Funnel & Why Discounting Is A Great Tool with Sam Blond, Chief Sales Officer @ Brex 16.07.2018 30:43
Sam Blond is Chief Sales Officer @ Brex, the startup that provides corporate cards for startups. To date they have raised over $57m in funding from the likes of Y Combinator, Peter Thiel, Max Levchin, Yuri Milner, Elad Gil and many more incredible names. Prior to Brex, Sam Was Chief Revenue Officer at Rainforest QA. Before Rainforest, Sam saw firsthand the hypergrowth scaling of Zenefits as VP of...
SaaStr 183: Intercom CEO, Eoghan McCabe on The Right Way To Structure Your Org Chart, The Secret To Scaling From SME To Enterprise Successfully & How To Create A Culture of Experimentation Without Fear 09.07.2018 48:58
Eoghan McCabe is the Co-Founder & CEO @ Intercom , one of the fastest growing saas companies of the day providing a new and better way to acquire, engage and retain customers. Due to their phenomenal growth they have raised over $240m in funding from some of the best in the world including Kleiner Perkins, Social Capital, Bessemer and Index, just to name a few. As for Eoghan, prior to co-founding...
SaaStr 182: Marketo CEO, Steve Lucas on What Makes A Truly Great SaaS CEO Today, The Top Considerations You Must make Before Going To Enterprise & Why The Way We Sell Has To Fundamentally Change 02.07.2018 31:31
Steve Lucas is the CEO @ Marketo , the world leader in marketing automation for companies of any size. Prior to their IPO and eventual sale to Vista Equity partners for $1.79Bn they raised over $100m in VC funding from the likes of Battery Ventures, IVP, Mayfield and Lead Edge Capital. As for Steve, prior to joining Marketo, he served in many leadership positions at SAP, Salesforce, Microsoft, Bus...
SaaStr 181: How To Gain Enterprise Clients As A Startup, How To Approach Multi-Year and Prepaid Deals with Those Mega Companies & How To Balance Fast Growth Expectations with Profitability with Jerry Jao, Founder & CEO @ Retention Science 25.06.2018 31:20
Jerry Jao is the Founder & CEO @ Retention Science , the startup that brings intelligence to your marketing automation through artificial intelligence that delivers a personalized customer experience, at scale. To date, Jerry has raised over $10m in VC funding with Retention Science from great friends of the show in Forerunner Ventures, Upfront Ventures, Clark Landry, Andy Rankin and more fantasti...
SaaStr 180: David Skok on Why You Should Not Focus On CAC/LTV In The Early Days, What Is The Right Way To Analyse Sales Rep Productivity & The Leading Indicators Early Stage VCs Use to Assess Product Market Fit 18.06.2018 30:58
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 successf...
SaaStr 179: What It Means To Be An ARR First SaaS Company, The Most Commonly Misunderstood SaaS Metrics & Why Renewals Does Not Mean Happy Customers with Dave Kellogg, CEO @ Host Analytics 11.06.2018 30:05
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, G...
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