Shows / The Official SaaStr Podcast: SaaS | Founders | Investors
The Official SaaStr Podcast: SaaS | Founders | Investors
The Official SaaStr AI Podcast. How to scale with the best in AI + B2B.
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Episodes
The Official SaaStr Podcast: SaaS | Founders | InvestorsThe Latest 20VC + SaaStr: Was $3B Really Left on the Table, Broken CEO Comp, and Why VCs Are Worse Than Public Markets
The latest 20VC + SaaStr: The Figma IPO Breakdown: $3B Left on the Table, Broken CEO Comp, and Why VCs Are Worse Than Public Markets This week, Brian Halligan…
The Official SaaStr Podcast: SaaS | Founders | InvestorsFrom $30M to $11B: The ServiceTitan Playbook - CRO Ross Biestman's Masterclass on Vertical SaaS
Ross Biestman joined ServiceTitan in 2018 as employee #354 when the company was doing less than $30M ARR. As Head of Sales, he helped scale the vertical SaaS…
The Official SaaStr Podcast: SaaS | Founders | InvestorsAI in GTM Efficiency: The Playbooks from Databricks, Monday.com and Benchling
How three high-growth companies are actually implementing AI across their revenue operations — and what it means for your AI-informed GTM strategy today. The…
The Official SaaStr Podcast: SaaS | Founders | InvestorsAI and Cybersecurity: How Rubrik’s Co-Founder Built a $1B+ ARR Platform While Joining the AI Revolution
Lessons from Arvind Nithrakashyap, Co-Founder and CTO of Rubrik, on scaling cyber resilience platforms, building multiple product curves, and implementing AI…
The Official SaaStr Podcast: SaaS | Founders | InvestorsAI and the Bottom Line with Canva's CCO: How They Built a $7B Enterprise Motion on 16 Billion AI Interactions
Rob Giglio, Canva's Chief Customer Officer, shares the playbook for scaling from 170M to 230M monthly active users while building enterprise sales without…
The Official SaaStr Podcast: SaaS | Founders | InvestorsSaaStr Live: How Wiz's CMO Built a $32B Marketing Machine (Without Any Marketing Experience)
The Most Unconventional CMO Story in B2B Raaz Herzberg joined Wiz as employee #5. She led product for 2.5 years. Then their CEO asked her to take over…
The Official SaaStr Podcast: SaaS | Founders | InvestorsThe $4.5B Board Meeting: Inside Snowflake’s AI Transformation and the CEO Who Bet His Company on Their Platform
Inside Snowflake’s Board Meetings: How AI is Reshaping Enterprise Data and the Future of B2B Partnerships We had a lot of fun at SaaStr AI Summit 2025 with a…
The Official SaaStr Podcast: SaaS | Founders | InvestorsThe HubSpot AI Playbook: How Yamini Rangan Is Leading the Most Aggressive AI Transformation in B2B
The HubSpot AI Playbook: How Yamini Rangan Is Leading the Most Aggressive B2B AI Transformation HubSpot's CEO came to SaaStr + AI Summit to do a deep and…
The Official SaaStr Podcast: SaaS | Founders | InvestorsPerplexity's CBO: Speed is The New Moat in AI Sales
Perplexity's CBO Dmitry Shevelenko joined Sam Blond ex-CEO of Brex at 2025 SaaStr + AI Summit for a deep dive on AI and Sales. More on the full session coming…
The Official SaaStr Podcast: SaaS | Founders | InvestorsAI Adoption: 5 Hard Truths About the Fastest Technology Transformation in History With Aaron Levie, CEO Box
We’ll do deep dives on all the SaaStr + AI Summit 2025 speakers soon! We wanted to kick it off with some of the key insights with Box CEO Aaron Levie and IBM…
The Official SaaStr Podcast: SaaS | Founders | InvestorsAI and the Future of Enterprise: A SaaStr Deep Dive with Marc Benioff
"The Last Generation of Human-Only CEOs: Marc Benioff's Bold Vision for the AI-Augmented Enterprise" Marc Benioff was kind enough to join SaaStr for the first…
The Official SaaStr Podcast: SaaS | Founders | InvestorsThe Real Data on What it Takes to Go Big and Eventually IPO with Meritech Capital
Want to know what it really takes to go public today? Let’s dive into the fascinating data and insights from Meritech Capital’s Alex Clayton and Cathy Choi…
The Official SaaStr Podcast: SaaS | Founders | InvestorsThe Playbook for Going Upmarket with Stripe’s CBO and Checkr’s COO
Want to know when to move upmarket and how to actually pull it off? Jeanne Dewitt Grosser (Chief Business Officer at Stripe) and Lindsey Scrase (COO at Checkr)…
The Official SaaStr Podcast: SaaS | Founders | InvestorsHow Tooey Courtemanche Built a $1B+ ARR Construction SaaS Empire Over 23 Years
What does it take to build and scale a vertical SaaS giant over two decades? According to Tooey Courtemanche, CEO and Founder of Procore, it’s about focus…
The Official SaaStr Podcast: SaaS | Founders | InvestorsThe Future of AI in SaaS Sales with Henry Schuck, CEO of ZoomInfo and SaaStr CEO Jason Lemkin
SaaStr CEO Jason Lemkin joined ZoomInfo’s as its opening guest alongside ZoomInfo CEO Henry Schuck. Along with co-host Ben Salzman, Jason and Henry discuss the…
The Official SaaStr Podcast: SaaS | Founders | InvestorsHow to Hire a Great VP of Sales Today: The New, Latest Edition with Jason Lemkin (Video + Pod)
What are the top 10 mistakes founders are still making today when hiring their VP of Sales? SaaStr CEO and Founder, Jason Lemkin, has done numerous surveys now…
The Official SaaStr Podcast: SaaS | Founders | Investors5 Interesting Learnings from Monday at $1 Billion in ARR
So Monday is just a freight train right now. It just keeps scaling and scaling. It’s now crossed $1B in ARR, still growing a stunning 34% … with 22% Free Cash…
The Official SaaStr Podcast: SaaS | Founders | InvestorsTop 10 Go-To-Market Mistakes Founders Make Today with SaaStr CEO Jason Lemkin
If you’ve read SaaStr or have been around for the last decade, you might be familiar with some of the repeated GTM mistakes founders tend to make, but the…
The Official SaaStr Podcast: SaaS | Founders | InvestorsThe Top 16 Rookie Errors Pitching VCs
Pitching VCs is like anything. You’ll get better at it over time. Later, you’ll even get great at it. Once you know how it works, it’s not even that hard to…
The Official SaaStr Podcast: SaaS | Founders | InvestorsWhat I Learned Selling My Company for $130M with Harry Glaser Founder of Periscope Data and ModelBit
A little while back, Harry Glaser sold his SaaS analytics startup, Periscope Data, for $130M. It was a difficult, punishing, and rewarding experience. At a…
The Official SaaStr Podcast: SaaS | Founders | InvestorsFour Sales Compensation Tactics for Consumption-Based GTM with MongoDB’s SVP of Sales Ops
A Story About A Cobra Meghan shared a fable. Once upon a time, there was a village with a cobra problem. There were too many cobras, and they were a menace…
The Official SaaStr Podcast: SaaS | Founders | InvestorsHitting Hypergrowth: How To Take Your SaaS Company from $25M to $100M and Beyond with Amplitude’s CEO, Spenser Skates
As you grow from nothing to $100M and beyond, you will run into a unique set of challenges at every stage. Spenser Skates, CEO and co-founder at Amplitude took…
The Official SaaStr Podcast: SaaS | Founders | InvestorsCRO Confidential: How to Sell in a Hyper-Competitive Space with Apollo CRO Leandra Fishman
How do you sell against the competition or become a market leader in a very crowded space? SaaStr’s CRO Confidential podcast host Sam Blond chats with the CRO…
The Official SaaStr Podcast: SaaS | Founders | InvestorsSeed May Still Be Strong, But There's No Bounce Back at Series A: Redpoint's Data and More
So Redpoint Ventures published some of the slides they recently presented to their Limited Partners (their own investors) here. There's a ton of good data…
The Official SaaStr Podcast: SaaS | Founders | InvestorsHow to Take Care of Yourself as a Founder
Dear SaaStr: How Do You Take Care of Yourself As a Founder? Quiet quitting, feeling sorry for yourself, working 30 hours a week, etc. — that doesn’t really…
The Official SaaStr Podcast: SaaS | Founders | InvestorsA Checklist: 10 Signs You Shouldn’t Hire a Sales Rep -- or VP of Sales
So you’re hiring your first few sales reps in the early days? Before you have a great VP of Sales? It’s an interesting time. Leads are precious, everyone is a…
The Official SaaStr Podcast: SaaS | Founders | Investors5 Interesting Learnings from Okta at $2.5 Billion in ARR
So Okta is one of our favorite SaaS and Cloud leaders. The story is super inspiring. Founder CEO Todd McKinnon was VP of Engineering at Salesforce and left to…
The Official SaaStr Podcast: SaaS | Founders | Investors6 Questions Founders Should Ask Themselves to Drive Value from Generative AI with Base10 Partners
Generative AI is a platform shift where models can take inputs such as text, image, audio, video, and code and generate new content into any of the modalities…
The Official SaaStr Podcast: SaaS | Founders | Investors5 Interesting Learnings from Braze at $500,000,000 in ARR
So Braze is one of the quiet winners in today’s SaaS and Cloud world. At $500m in ARR, they’re growing a strong 33% and trading at about $6 Billion, so they’re…
The Official SaaStr Podcast: SaaS | Founders | InvestorsA Look Back: The Top 10 Learnings From Ben Chestnut, CEO of Mailchimp
As we gear up for SaaStr Europa 2024 in London on 4-5 June and SaaStr Annual 2024 in the SF Bay Area on September 10-12, we wanted to take a look back at some…
The Official SaaStr Podcast: SaaS | Founders | InvestorsCRO Confidential: Bringing Product-Led and Sales-Led Growth Together For Go-To-Market Success with Giancarlo Lionetti, CRO of Zapier
In this latest episode of CRO Confidential, Sam Blond, Partner at Founders Fund and former CRO at Brex, sits down with the CRO of Zapier, Giancarlo Lionetti…
The Official SaaStr Podcast: SaaS | Founders | InvestorsSaaStr 393: 3 Secrets to Selling Up-Market with the Leaders of Stripe, DocuSign and Lever
The journey for a company to move upmarket can be daunting and varies widely depending on the internal and external factors that inspire a shift in…
The Official SaaStr Podcast: SaaS | Founders | InvestorsSaaStr 392: 10 Simple Steps To Help Any Sales Exec Close More with SaaStr CEO and Founder Jason Lemkin
In today's SaaStr insider episode SaaStr CEO Jason Lemkin shares 10 Simple Steps To Help Any Sales Exec Close More. This is a public episode. If you would like…
The Official SaaStr Podcast: SaaS | Founders | InvestorsSaaStr 391: The Secrets to Bootstrapping to $5M ARR in Less than a Year with Martha Bitar, CEO @ Flodesk
Learn how Flodesk bootstrapped to $5M in ARR by focusing on customer-driven growth: from kickstarting growth by empowering new customers to share, to creating…
The Official SaaStr Podcast: SaaS | Founders | InvestorsSaaStr 390: How To Crush It With Interactive Content, What Type, Where and When To Use It Most Efficiently and Where Many People Make Mistakes with Randy Rayess, Founder @ Outgrow
Randy Rayess is the Co-Founder @ Outgrow, a growth marketing platform that enables marketers to build interactive content/tools to increase customer engagement…
The Official SaaStr Podcast: SaaS | Founders | InvestorsSaaStr 389: How To Really Disrupt the Big Guys With Free with Mikael Cho, CEO @ Unsplash and Kinsey Grant, Business Editor and Podcast Host @ Morning Brew
Mikael Cho, CEO of Unsplash shares his lessons learned from starting Unsplash as a side project and growing it to a market leader, and disrupting an industry…
The Official SaaStr Podcast: SaaS | Founders | InvestorsSaaStr 388: Okta CMO, Ryan Carlson on How To Measure Marketing Attribution Effectively, Why People Think About Category Creation Incorrectly Today & How You Have To Think Through The Product vs The Company Story
Ryan Carlson is the CMO @ Okta, the leading independent provider of identity for the enterprise. Prior to their incredibly successful IPO in April of 2017…
The Official SaaStr Podcast: SaaS | Founders | InvestorsSaaStr 387: Where Product Development is Going in 2021 with Nick Mehta, CEO @ Gainsight and Jason Lemkin, CEO @ SaaStr
In this CEO to CEO catch up, Nick Mehta and Jason Lemkin discuss how to do product extensions, how to sell a second product, and where product development…
The Official SaaStr Podcast: SaaS | Founders | InvestorsSaaStr 386: How to Win When There are 1000 Players in Your Market with Adam Blitzer, EVP & GM @ Salesforce Digital Marketing Cloud
How do you compete in a tough marketplace with thousands of other competitors? Join Adam Blitzer as he shares insights from launching a company in an already…
The Official SaaStr Podcast: SaaS | Founders | InvestorsSaaStr 385: How To Approach Core Product Decisions in SaaS, Why Storytelling is a Lost Art in SaaS & How Product and Marketing Can Work Together Most Efficiently with Paul Rosania, Founder & CEO @ Balsa
Paul Rosania is the Founder & CEO @ Balsa, the company that recognises that builders move the world forward and so they are building the best second screen for…
The Official SaaStr Podcast: SaaS | Founders | InvestorsSaaStr 384: When to Launch a Second Product with Dharmesh Shah CTO and Co-Founder @ Hubspot and Jason Lemkin, CEO @ SaaStr
We caught up with one of the SaaStr community’s favorite speakers, Dharmesh Shah CTO and co-founder of Hubspot on lessons learnings launching a second product…
The Official SaaStr Podcast: SaaS | Founders | InvestorsSaaStr 383: Growing Product and Engineering Orgs from Zero to IPO with Nick Caldwell, VP of Engineering @ Twitter, and Tomasz Tunguz, Managing Director @ Redpoint Ventures
Nick Caldwell has built and grown product and engineering organizations at PowerBI (0 to 300 engineers), Reddit (500M MAU) and Looker ($2.7B sale to Google)…
The Official SaaStr Podcast: SaaS | Founders | InvestorsSaaStr 382: What's Next For B2B and Cloud Events in 2021 with Amelia Ibarra, SVP & GM @ SaaStr, and Alon Alroy, Co-Founder & CMO @ Bizzabo
In today's SaaStr Insider, SaaStr SVP & GM, Amelia Ibarra, sits down with Alon Alroy, Co-Founder & CMO at Bizzabo on What's Next For the Future of B2B Events…
The Official SaaStr Podcast: SaaS | Founders | InvestorsSaaStr 381: Churn is dead. Long Live Net Dollar Retention Rate with Dave Kellogg, Principal @ Kellogg Consulting
There are a lot of problems with calculating churn rates. Moreover, public companies don't generally release churn rates. Learn what they are and how to…
The Official SaaStr Podcast: SaaS | Founders | InvestorsSaaStr 380: How To Effectively Sell Into Mid-Market, Why SEO Is The Best Kept Secret In SaaS & How To Show Credibility To Enterprise Customers as a Startup
Ryan Sandler is the Co-Founder and CEO @ Truework, the company that gives employees control over employment, income and other identity data. To date, Ryan has…
The Official SaaStr Podcast: SaaS | Founders | InvestorsSaaStr 379: The Top 10 Mistakes Founders Make When Hiring Their First Sales Team with SaaStr CEO and Founder Jason Lemkin
From how many reps to hire, to compensation models, here are the top 10 mistakes founders make when hiring their first sales teams and how to avoid them. This…
The Official SaaStr Podcast: SaaS | Founders | InvestorsSaaStr 378: The 5 Things That Kill Startups After Their Seed Rounds and How to Avoid them with Michael Seibel, CEO @ Y Combinator
Investment can create more problems than it solves and founders may trick themselves into thinking they have product-market fit when they don't. Michael…
The Official SaaStr Podcast: SaaS | Founders | InvestorsSaaStr 377: Hashicorp CEO Dave McJannet on Scaling Remote Teams; What Breaks and When, How To Successfully Execute Multi-Product Strategies and How Leadership Style Evolves with Company Stage
Dave McJannet is the CEO @ Hashicorp, one of the fastest-growing enterprise companies of our time providing consistent workflows to provision, secure, connect…
The Official SaaStr Podcast: SaaS | Founders | InvestorsSaaStr 376: 10 Mistakes the CEO of ZoomInfo Made on His Journey to IPO with Henry Schuck, CEO @ ZoomInfo and Jason Lemkin, CEO @ SaaStr (Part 2)
In part two, ZoomInfo founder and CEO Henry Schuck shares how he built a business from scratch and grew it into one of the most successful IPOs of the 21st…
The Official SaaStr Podcast: SaaS | Founders | InvestorsSaaStr 375: What Being a Founder Taught Me About Leadership - Lessons from GitHub’s COO, Erica Brescia
GitHub’s COO, Erica Brescia, shares her experiences and lessons learned from her former life on the front lines of being a co-founder of her own company, and…
The Official SaaStr Podcast: SaaS | Founders | InvestorsSaaStr 374: 10 Mistakes the CEO of ZoomInfo Made on His Journey to IPO with Henry Schuck, CEO @ ZoomInfo and Jason Lemkin, CEO @ SaaStr (Part 1)
ZoomInfo founder and CEO Henry Schuck shares how he built a business from scratch and grew it into one of the most successful IPOs of the 21st century—and what…
The Official SaaStr Podcast: SaaS | Founders | InvestorsSaaStr 373: The State of the Cloud 2020, The COVID Beneficiaries Edition with Byron Deeter and Elliott Robinson of Bessemer Venture Partners
Bessemer's 5th Annual State of the Cloud Report returns for a definitive look at the cloud industry today. Byron Deeter and Elliott Robinson, partners at…
The Official SaaStr Podcast: SaaS | Founders | InvestorsSaaStr 372: Sales Kick-Off Week: How To Prepare, How To Structure, How To Organise Content, How To Keep Teams Engaged with Latane Conant, CMO @ 6Sense
Latane Conant is the Chief Marketing Officer at 6Sense, the company that allows you to achieve predictable revenue growth by identifying accounts looking for…
The Official SaaStr Podcast: SaaS | Founders | InvestorsSaaStr 371: Learning from the Lows, How Mailchimp Navigated Economic Uncertainty with Ben Chestnut, CEO @ Mailchimp and Jason Lemkin, CEO and Founder @ SaaStr
It’s no secret that businesses today are struggling with an unpredictable economy. In this session, Mailchimp Co-founder and CEO Ben Chestnut will share the…
The Official SaaStr Podcast: SaaS | Founders | InvestorsSaaStr 370: Automation, The Digital Transformation Accelerator with Jennifer Tejada, CEO @ PagerDuty
As organizations race to achieve relevance and a competitive edge in the digital era, automation is fueling the fight. Join PagerDuty’s CEO, Jennifer Tejada…
The Official SaaStr Podcast: SaaS | Founders | InvestorsSaaStr 369: How to Hire an A-Player VP Sales and Scale Your Team with SaaStr CEO and Founder Jason Lemkin and the Co-founder and CEO of HireSweet, Robin Choy
In today’s SaaStr Insider episode, SaaStr CEO and Founder Jason Lemkin and the Co-founder and CEO of HireSweet, Robin Choy, share their experiences building…
The Official SaaStr Podcast: SaaS | Founders | InvestorsSaaStr 368: 5 Insights for Consumerization of the Enterprise with Scott Belsky, CPO and EVP @ Adobe Creative Cloud
Success in the Enterprise means ensuring consumerization is a part of your strategy. Scott Belsky, CPO, EVP of Creative Cloud at Adobe will explore key tactics…
The Official SaaStr Podcast: SaaS | Founders | InvestorsSaaStr 367: Zoom's Head of Global Sales Operations on Sales Ops vs Revenue Ops, The Biggest Areas of Operational and Strategic Debt for Sales Teams Today & The Importance of Documentation and The Dangers of Dirty Data
Hilary Headlee is Head of Global Sales Operations and Enablement @ Zoom. Prior to joining Zoom, Hilary was VP of Global Sales Operations and Productivity @…
The Official SaaStr Podcast: SaaS | Founders | InvestorsSaaStr 366: Digital Transformation At Warp Speed with Jason Lemkin, CEO and Founder @ SaaStr, and Aaron Levie, CEO, Co-founder and Chairman @ Box
The buzz that accompanies digital transformation trends is infinite. Cut through the noise with Aaron Levie, CEO of Box and Jason Lemkin, CEO & Co-founder of…
The Official SaaStr Podcast: SaaS | Founders | InvestorsSaaStr 365: The Office of the Future, How Everything's Changed and What 2021 Will be Like with Justin Bedecarre, CEO @ HelloOffice and Jen Nguyen, Founding Partner @ TEAMWERC
Centralized HQs with all the perks and amenities “under one roof” have traditionally been used as recruiting tools to attract and retain top talent. In this…