The Official SaaStr Podcast: SaaS | Founders | Investors

This week Canva Co-Founder and COO Cliff Obrecht joined Harry Stebbings, Rory O’Driscoll and Jason with honest, unfiltered insights on scaling to 240 million users, navigating AI transformation, and preparing for public markets. Canva’s CoFounder Joins 20VC + SaaStr on The Coming IPO, Where AI Works Today, Employee Liquidity, Figma’s IPO, and Much More! After 13 years building Canva into a $4 bill...

We had a great one this week — Marc Benioff joined Harry, Rory, and Jason on 20VC+SaaStr this week to deliver one of the most grounded and passionate takes on AI we’ve heard from any enterprise leader. In a market fueled by AGI promises and $10 billion funding rounds, Salesforce CEO’s cut through the hype while revealing his company is quietly building a billion-dollar AI business — by focusing on...

When you think about Product-Led Growth (PLG) success stories, few companies exemplify the model better than Calendly. Founded in 2013 by Tope Awotona, Calendly has grown from a simple scheduling tool to a scheduling powerhouse that's touched "double digits" of the world's billion knowledge workers - meaning over 100 million people have used the platform at some point. At SaaStr Annual + AI Summit...

Gusto co-founders Josh Reeves (CEO) and Eddie Kim (CTO) came to SaaStr AI Summit to share their journey building “Gus,” an AI assistant now used by hundreds of thousands of small businesses. Rather than chasing AI trends, they focused on solving real compliance pain points for small business owners navigating complex regulatory requirements across 50+ different state and local jurisdictions. Their...

The latest 20VC x SaaStr episode with Harry Stebbings, Jason Lemkin, and Rory O’Driscoll is here! The team is discussing Databricks’ $100B valuation, the coming IPO tsunami, CoreWeave’s massive debt raise, AI infrastructure spending that could hit trillions, the return of SPACs as a bubble signal, and why AI tool consolidation will happen faster than anyone expects Bottom Line Up Front Harry Stebb...

At SaaStr's packed AI Summit 2025 , Box CEO Aaron Levie and IBM VP of AI Raj Datta did a deep dive together with SaaStr's Jason Lemkin on how B2B companies should think about AI agents. With 10,000 attendees—a massive jump from last year—the energy around AI agents was electric. Here are the top 10 learnings from their convo: 1. AI Agents Represent a Fundamental Shift from Software to Digital Labo...

How We Built ChatGPT Enterprise's Sales Team from Absolute Zero: The Complete Playbook with Maggie Hott, GTM Leadership at OpenAI About Maggie: Maggie Hott has spent 15 years building go-to-market teams at four unicorns that collectively represent over $50B in market value. She started as the 2nd SDR at Eventbrite, became the first sales hire at Slack (helping scale from $50M to $1B ARR and a $27B...

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 (Co-Founder & Executive Chairman of HubSpot) joins the regular crew of Harry Stebbings, Rory O’Driscoll, and Jason Calacanis for an inside look at IPO dynamics, CEO compensation, and the current state of public markets. The Bottom Line Up Fr...

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 platform from Series B to IPO, growing revenue to over $860M ARR and achieving an $11B market cap. Before ServiceTitan, Ross spent nearly a decade in enterprise software sales, serving companies like Bloomberg, United Airlines, and Sprint. A...

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 AI transformation in go-to-market isn't coming — it's here. But unlike the broad promises we've been hearing, the real story is in the specifics. How are actual revenue leaders at scale implementing AI today? What's working, what isn't, and w...

Lessons from Arvind Nithrakashyap, Co-Founder and CTO of Rubrik, on scaling cyber resilience platforms, building multiple product curves, and implementing AI across both products and operations. Company Snapshot: * Founded: January 2014 (11 years) * Current ARR: $1.09B+ (Q1 FY2025) * Growth Rate: 39% YoY ARR growth, 47% revenue growth * NPS Score: 80 (exceptionally high for enterprise software) *...

Rob Giglio, Canva's Chief Customer Officer, shares the playbook for scaling from 170M to 230M monthly active users while building enterprise sales without compromising company culture. Top 5 Takeaways 1. PLG-to-SLG is Far Easier Than SLG-to-PLG Going from product-led growth to sales-led growth is significantly easier than the reverse. Companies with strong PLG foundations have rich product usage d...

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 marketing. Her response? "No. What are you talking about?" Today, Wiz is in the process of being acquired for a stunninga $32 billion by Google. And Raaz just shared exactly how she built their marketing engine from zero marketing experience to hype...

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 rare look inside Snowflake’s boardroom! We featured an unprecedented dynamic: Jeremy Burton sits on Snowflake’s board while simultaneously running Observe, a company built 100% on Snowflake’s platform. Together with Snowflake’s CEO, Sridhar R...

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 honest dive on how she's transforming the company into an AI-first $2.75B+ ARR B2B leader. And what it means for the future of B2B software. The January 2023 Pivot That Changed Everything HubSpot had spent four months meticulously planning your 2...

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 soon but this deep dive on being prepared for meeting prospects in the Age of AI was super interesting. The 90-Minute Meeting Prep is Dead Here's a hard truth every CRO, VP of Sales, AE and founder needs to hear: You have no excuse to not be...

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 VP AI Raj Datta: The Numbers Don’t Lie – ChatGPT Hit 500M Users in Just ~2 Years Let’s start with the cold, hard metrics that SaaS leaders seem to underestimate: AI adoption is happening at an unprecedented velocity. As Aaron Levie, CEO of Bo...

"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 time to do a truly deep dive on what AI means in business software today. From how quickly humans will be replaced in some functions ... to how slow some traditional enterprises will be to change. It's a good one. Top 5 Unexpected Learnings:...

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, who have helped guide dozens of companies through successful IPOs over the past 25 years. First, let’s address a common misconception: while many founders dream of going public, the reality is that only about 20 SaaS companies manage to IPO ea...

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) have done it multiple times at companies like Google Cloud, Stripe, and Checkr. They came to SaaStr Annual to share what they’ve learned about making the move to go more enterprise actually work. A Bit About Our Enterprise Leaders Jeanne De...

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, perseverance, and a relentless commitment to customer success. In a recent conversation with SaaStr CEO and Founder Jason Lemkin, Tooey shared insights into his 23-year journey as CEO of Procore , the leading SaaS platform for construction mana...

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 transformative power of AI within SaaS and the evolving dynamics that are reshaping the landscape of software as a service. There’s recruiting and there’s people building. On the topic of building SaaS companies, Henry kicks off the convers...

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 that confirm that a startling 70% of first VPS hires still don’t make it . In this post, we’ll delve into the common pitfalls founders encounter when hiring a VP of Sales. Reflecting on twelve years of SaaStr’s hiring lessons, we’ll take a...

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 Flow margins! That’s as good as it gets in SaaS, folks.  Jaw dropped. What are the secrets?  A few, but 2 stand out: * Going multiproduct early * 70% of their customers are outside of tech.  So they’ve been immune from most “macro” impacts...

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 world of hiring, people, scaling, and workplace expectations are significantly different today than they were before March 2020. SaaStr Founder and CEO, Jason Lemkin, shares the top GTM mistakes founders make today and some cheat codes to avoid...