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.
cloud.substack.com
Episodes
The Official SaaStr Podcast: SaaS | Founders | InvestorsTop 5 Learnings from Vercel’s COO: 10 SDRs Down to 1, a $5K-a-Year Lead Agent, and 93% of Support Cases Handled by AI
Vercel used to have 10 people qualifying inbound leads. Six weeks after it turned on an agent, it had one. The agent doing the rest of the work costs under…
The Official SaaStr Podcast: SaaS | Founders | InvestorsDatabricks CRO Ron Gabrisko: 5 Interesting Learnings on Selling at a $190B AI Company: Flat SDR Headcount, 6-10% Reply Rates, and Free Seats That Unlocked Consumption
Ron Gabrisko joined Databricks as CRO when it was doing under $1M in ARR. Databricks is now a ~$190 billion company doing $7B+ ARR growing at a rate like we’ve…
The Official SaaStr Podcast: SaaS | Founders | InvestorsThe Agent-Led Growth Playbook: A 10-Minute Inbound Booking, a 46-of-50 AEO Score, and Why First-Party Data Beats Every Signal Tool | The Agents #017
We ran a live edition of The Agents this week to walk through our agent-led growth stack as it stands today. We talked about “ask your agent instead of your…
The Official SaaStr Podcast: SaaS | Founders | InvestorsOwner.com Did an AI Rebuild to Accelerate Past $100M ARR. The 7 Top Lessons, and What It Takes to Copy Them
Adam Guild CEO of Owner.com gave one of the more useful operator talks at SaaStr AI 2026 this year: three years of rebuilding Owner.com around AI, from a…
The Official SaaStr Podcast: SaaS | Founders | InvestorsKlaviyo’s CEO on Building at $1.5B ARR With Agents: “Dark Factory,” Composer, and Why Every Single Employee Had to Hit L3 by June
Klaviyo co-founder and co-CEO Andrew Bialecki came to SaaStr AI to walk through how a 2,300-person public company builds AI products. Not the vision deck. The…
The Official SaaStr Podcast: SaaS | Founders | InvestorsClaude Became Our AI VP of Product. We Moved 10 Years Off Marketo for $14. Our Agent Killed a $10K App in an Hour: The Agents #010
Amelia and I just shipped Episode #010 of The Agents. Same setup as always: three humans, 21+ agents in production, an 8-figure B2B + AI business, revenue…
The Official SaaStr Podcast: SaaS | Founders | Investors$500M ARR, 60 Engineers, Cash-Flow Positive: How Higgsfield Actually Runs, With CEO Alex Mashrabov
We use Higgsfield almost every day at SaaStr AI. If you’ve watched any of our short videos, the intro to The Agents with me and Amelia, the event promos, the…
The Official SaaStr Podcast: SaaS | Founders | InvestorsDatabricks' Co-Founder Arsalan Tavakoli: Every Software Monopoly Falls in the Next 24 Months
Databricks is now running at a stunning $6.9B revenue run-rate, growing 80%+ year over year, with AI products alone past a $1.7B run-rate and net retention…
The Official SaaStr Podcast: SaaS | Founders | InvestorsHow To Build Your Own AI VP of Marketing: The Full 10K Playbook From SaaStr AI 2026
At SaaStr AI 2026, Amelia Lerutte, SaaStr’s Chief AI Officer, took five months of running 10K, SaaStr’s AI VP of Marketing, distilled what worked into a spec…
The Official SaaStr Podcast: SaaS | Founders | InvestorsAmjad Masad and Me: The AI Agents We Actually Built, and What Replit's Founder Thinks Comes Next
We we fortunate enough to get Amjad Masad, co-founder and CEO of Replit, on stage live at SaaStr AI 2026 to react in real time to the agents we run SaaStrAI…
The Official SaaStr Podcast: SaaS | Founders | InvestorsSnowflake’s CMO Runs Marketing for 700 People. She Starts Her Day By Talking to Her Data, Not a Dashboard.
Denise Persson runs marketing for Snowflake. That’s a 700-person org, new-business pipeline she’s personally accountable for, and a level of compliance and…
The Official SaaStr Podcast: SaaS | Founders | Investors$400M ARR With Under 200 People: What Lovable’s Head of Growth Elena Verna Says Actually Works in B2B Now
When Elena Verna, Head of Growth at Lovable, took the stage at SaaStr AI 2026, she’d just hit her one-year anniversary at the company. She also walked through…
The Official SaaStr Podcast: SaaS | Founders | InvestorsThe Agents Episode #006: We Run SaaStrAI on 3 Humans and 21+ AI Agents. Here’s Every Agent, Agent by Agent, With the Numbers.
The Agents is our weekly podcast on how we deploy and run AI agents at SaaStr, and how to do it yourself. We run SaaStr AI on 3 humans and 21+ AI agents. At…
The Official SaaStr Podcast: SaaS | Founders | InvestorsHow Owner.com’s CRO Is Closing $2M+ in ARR Per Rep With AI: 5 Things You Can Steal
At SaaStr AI 2026, Kyle Norton, CRO of vertical AI leader for restaurants Owner.com, walked through how his team is generating outcomes that look almost…
The Official SaaStr Podcast: SaaS | Founders | InvestorsThe Agents Episode #005 is Out! Our 2 AI VPs Cost $257/Month, a Website Willed Itself Into Becoming an Agent, and QBee Sent 83 Personalized Emails at 12:20am
Amelia and I just recorded Episode 005 of The Agents. We both got the cost number completely wrong. Our AI VP of Marketing (10K) and our AI VP of Customer…
The Official SaaStr Podcast: SaaS | Founders | InvestorsHow Anthropic Rebuilt Its Sales Org From Scratch When Demand Went Vertical: 54% of New Enterprise Logos Now Come Self-Serve
When Claude Opus 4.6 shipped in December 2025, Anthropic’s commercial team came back from winter break to find demand had gone vertical. They hadn’t hired for…
The Official SaaStr Podcast: SaaS | Founders | InvestorsTragedy Apps, Database Deletions, AI PR Pitches I Block on Sight, and Why We’re Hiring a Marketer to Report to an AI Agent: The Agents #004 is Out!
Amelia and I just shipped Episode #004 of The Agents. Same setup: three humans, 20+ agents, revenue went from -19% to +47% YoY, and every week we get into…
The Official SaaStr Podcast: SaaS | Founders | InvestorsOur Own AI Agent Deleted Amelia, HubSpot Gave Us a Zero, and 100 Days Since I Opened Canva: The Agents Episode #002
Amelia and I just released Episode #002 of The Agents. Same deal as always: three humans, 20+ agents, revenue went from -19% to +47% YoY, and every week we…
The Official SaaStr Podcast: SaaS | Founders | InvestorsIntroducing “The Agents”: A New Weekly Show Where We Share Everything Happening With Our 20+ AI Agents in Production. The Good, The Bad, and The Broken.
We get asked about our agents probably 50 times a week. CEOs of public companies. Founders just deploying their first AI SDR. RevOps leaders trying to figure…
The Official SaaStr Podcast: SaaS | Founders | InvestorsThe Top 10 Things to Know Before You Deploy Your First AI SDR With Jason Lemkin and Chief AI Officer Amelia Lerutte
We’ve now been running AI SDR agents for 10+ months at SaaStr: * We use four different vendors in daily rotation (Artisan, Salesforce AgentForce, Qualified…
The Official SaaStr Podcast: SaaS | Founders | InvestorsWe Have 30 AI Agents in Production. Here Are the Top 5 Issues No One Talks About
We’ve been running AI agents in production at SaaStr for about 10 months now. What started as a couple of experiments has turned into almost 30 agents and…
The Official SaaStr Podcast: SaaS | Founders | InvestorsMike Cannon-Brookes CEO Atlassian on Why B2B Software Isn’t Dead, Why CEOs Need to Stop Whining, and What Actually Matters Now
We did a deep dive on 20VC x SaaStr this week with Mike Cannon-Brookes, co-founder and CEO of Atlassian. Atlassian just put up an incredible quarter of…
The Official SaaStr Podcast: SaaS | Founders | InvestorsInference is the New Sales & Marketing Spend
High inference costs are OK—if they make your product so viral and so competitive it almost sells itself Here’s the counterintuitive insight that’s reshaping…
The Official SaaStr Podcast: SaaS | Founders | InvestorsFrom 1 AI Agent to 20+: The Reality of Managing Multiple AI Agents Across Your GTM
There’s a growing wave of AI agent skepticism on LinkedIn right now. And some of it is earned. A lot of founders bought an AI SDR, didn’t train it, and got…
The Official SaaStr Podcast: SaaS | Founders | InvestorsIf Growth Isn't Accelerating, You're Not an AI Company. And 9 Other Hard Truths for B2B in 2026.
If Growth Isn’t Accelerating, You’re Not an AI Company. And 9 Other Hard Truths for SaaS in 2026. I had a great conversation with the TBPN crew the other day…
The Official SaaStr Podcast: SaaS | Founders | Investors“The Dumbest Idea I’ve Ever Heard” — How Own Became a $2B Salesforce Acquisition
A SaaStr AI deep dive with Sam Gutmann, CEO of Own, on building a billion-dollar backup company by saying “no” to almost everything. He joined Harpinder Singh…
The Official SaaStr Podcast: SaaS | Founders | InvestorsWhy Most B2B Companies Are Failing at AI (And How to Avoid It) with Intercom’s CPO
Paul Adams is Chief Product Officer at Intercom, leading Product Management, Product Design, Data Science, and Research. He joined when Intercom was just a…
The Official SaaStr Podcast: SaaS | Founders | InvestorsHow Filevine Went from SaaS to AI-Native at $200M+ ARR — And Now Makes More Revenue from AI Than SaaS (A Roadmap for the Rest of Us)
Ryan Anderson, CEO of Filevine, shared their AI transformation playbook at SaaStr AI London. Here’s the thing: their new AI revenue now exceeds their SaaS…
The Official SaaStr Podcast: SaaS | Founders | InvestorsHow Personio’s CRO Built an AI-Powered Go-To-Market in Just 6 Months: 5 Lessons and 5 Mistakes
Philip Lacor is the CRO of Personio, a $3B+ HR and payroll platform with 1,500 employees, 15,000 customers, and a 400-person sales team. He shared their AI…
The Official SaaStr Podcast: SaaS | Founders | InvestorsThe Present and Future of AI in Sales and GTM A Deep Dive with Jason Lemkin and Kyle Norton, CRO at Owner
Jason Lemkin led the seed round via SaaStr Fund in unicorn Owner.com, an AI solution revolutionizing how small restaurants manage their business. Kyle Norton…
The Official SaaStr Podcast: SaaS | Founders | InvestorsWe Deployed 20+ AI Agents and Replaced Our Entire Human SDR Team. Here's What Actually Works. (Video + Pod)
At SaaStr AI London, Amelia and I went deep on our AI SDR journey. We shared all our data, all the emails we’ve sent, all the performance metrics—everything…
The Official SaaStr Podcast: SaaS | Founders | InvestorsNo, Inbound Isn't Dead. The GTM Playbook Isn't Broken. But Your Moats Are Shrinking to Months.
I did an open AMA at SaaStr London last week, a classic part of each SaaStr AI event. But this one was different. It was urgency to the max. The room was…
The Official SaaStr Podcast: SaaS | Founders | Investors6 Months of AI SDRs: What's Worked, How They Brought In $1M+ in 90 Days, and the Real Data Everyone's Asking For
After deploying 5 AI SDRs across inbound, outbound, and follow-up—here’s the actual numbers, unexpected learnings, and what it really takes to make them work…
The Official SaaStr Podcast: SaaS | Founders | InvestorsThe First $100,000,000 ARR at Datadog: How Founder CEO Olivier Pomel Built a Customer-Centric Observability Giant
Ahead of SaaStr AI London on Dec 1-2 (See you there!) we’re taking a look back at some of our favorite sessions from our European events. It was so great when…
The Official SaaStr Podcast: SaaS | Founders | Investors20VC x SaaStr This Week: Why Most VCs Need to Step Aside, What’s Really Defensible Today, and How to Actually Attach to AI Revenue
We’re back! Harry, Rory and Jason! The venture capital playbook is broken. Not bent — broken. In the latest 20VC x SaaStr episode, Harry Stebbings, Jason…
The Official SaaStr Podcast: SaaS | Founders | InvestorsThe Reality of Managing 10 AI Agents in Production: What We’ve Learned Building Our AI-First Revenue Team at SaaStr
By the end of Q3, we’ll had 10 distinct AI agents running in production at SaaStr. 20 if you including less critical ones. Not as a tech experiment or…
The Official SaaStr Podcast: SaaS | Founders | InvestorsHow to Price Your AI-First Product: The Death of SaaS Pricing and the Rise of Transactional Models with Defy Ventures’ Medha Agarwal
Medha Agarwal is a Partner at Defy VC, where she focuses on investments in AI-first and vertical SaaS companies. She shares insights at SaaStr AI Summit 2025…
The Official SaaStr Podcast: SaaS | Founders | InvestorsThe Top 10 Mistakes I See In The VP of Sales Hiring Process
So we’ve spent a ton of time over the years on SaaS talking about hiring a great VP of Sales / CRO . Not only because it really matters, but because hiring the…
The Official SaaStr Podcast: SaaS | Founders | InvestorsWhy Only "WTF" Products Can Survive Today with Brett Queener Partner at Bonfire Ventures
Brett Queener is Partner at Bonfire Ventures, a $1B AUM seed-stage fund writing $3-4M checks into application software companies. He was employee #70 at…
The Official SaaStr Podcast: SaaS | Founders | InvestorsFrom Zero to Eight Figures in 18 Months: Decagon CEO’s Playbook for AI-Native SaaS Growth. And Why They Partnered With Accel
A SaaStr Annual + AI Summit conversation with Jesse Zhang, CEO of Decagon, and Sarah Ittelson, Partner at Accel Decagon Today: The Numbers Behind the Hype…
The Official SaaStr Podcast: SaaS | Founders | InvestorsWhat Every B2B Founder Needs to Know About AI in Go-To-Market Right Now With Jason Lemkin
The State of AI + Software: Where It’s Going - Fast This deep dive is from Jason Lemkin at the LIVE AI Workshop Wednesday. Sign up here for the next one. I was…
The Official SaaStr Podcast: SaaS | Founders | InvestorsFrom Zero to 20 AI Agents in 10 Months: The SaaStr Playbook for Actually Deploying AI Agents That Work
A deep dive into the playbook, lessons learned, and brutal truths about deploying 20+ AI agents into production — that actually work. During Dreamforce Jason…
The Official SaaStr Podcast: SaaS | Founders | InvestorsFrom Zero to "Replit Fluent": How 9 Apps and 500,000 Users Taught Me to ‘Vibe’ Apps Into Production
I think after 100+ days and with 9 apps vibe coded into production with @replit used over 500,000 times we’re just getting going. And … I think key to that is…
The Official SaaStr Podcast: SaaS | Founders | Investors10 Ways Sales is Different in Vertical SaaS with Mangomint’s VP of Sales Marchelle Mooney
Marchelle Mooney, VP of Sales at Mangomint joined us at 2025 SaaStr Annual + AI Summit for one of our best deep dives on sales and GTM in vertical SaaS yet…
The Official SaaStr Podcast: SaaS | Founders | InvestorsVC Funding in the AI Era: What’s Actually Getting Funded in 2025 and Why Your B2B Startup Might Be Left Behind with Jason Lemkin
The VC fundraising landscape has completely transformed in the last 18 months, and most founders still don’t realize just how dramatically the rules have…
The Official SaaStr Podcast: SaaS | Founders | Investors20VC x SaaStr This Week: Are Burn Multiples BS in an AI World? Plus Sam Altman’s $1TRN Energy Problem, Zuck’s AI Strategy Crisis & The Great PE Reckoning
We’re back! Our latest deep dive with Jason Lemkin (SaaStr), Rory O’Driscoll (Scale Venture Partners), and Harry Stebbings (20VC). And come join the team LIVE…
The Official SaaStr Podcast: SaaS | Founders | InvestorsEnterprise Partnerships Bootcamp: How to Land, Scale, and Win with Linear’s COO, Omni’s CEO, Theory Ventures’s Tunguz, and Vesey Ventures
Tomasz Tunguz of Theory Ventures brought together a strong panel at SaaStr Annual and AI Summit for a deep dive on enterprise partnerships. An Enterprise…
The Official SaaStr Podcast: SaaS | Founders | InvestorsSaaStr Labs: Replit v3 ... Our Latest AI SDR Crushes It ... And 300,000 AI Startup Valuations
This week: * How the new Replit v3 is the Future: Agents Managing Agents, For Real * How our 4th AI “BDR” helps close deals 24x7, and is much better than a…
The Official SaaStr Podcast: SaaS | Founders | Investors20VC + SaaStr is Back!! NVIDIA’s $100B OpenAI Investment, H-1B’s $100K Fee Impact on Startups, and Is “Triple Triple Double Double” Really Dead?
Harry, Rory and Jason are back! We’re witnessing an unprecedented capital concentration in AI with NVIDIA’s $100B OpenAI investment creating a fascinating…
The Official SaaStr Podcast: SaaS | Founders | InvestorsThe GTM Playbook for Building a $300M+ ARR Business: Lessons from ClickUp’s COO Gaurav Agarwal
How to scale from startup to $300,000,000+ ARR by mastering the fundamentals of go-to-market strategy Building a billion-dollar B2B business isn’t about…
The Official SaaStr Podcast: SaaS | Founders | InvestorsThe Real Learnings From 1,000,000 AI Conversations with Clones of Brian Halligan, Lenny Rachitsky, Keith Rabois, and Jason Lemkin
The technical and product insights from Dara Ladjevardian’s AI cloning experiment at SaaStr Annual + AI Summit. The Clone Performance Reality Check When Dara…
The Official SaaStr Podcast: SaaS | Founders | Investors20VC x SaaStr Is Back!! Elon's $1 Trillion Pay Package, OpenAI's $10B Secondary, Sierra's $10B Valuation & The Great AI M&A Wave
We're back on 20VC + SasStr with Harry Stebbings, Jason Lemkin, Rory O'Driscoll, and special guest Jeff Lawson (Founder & Former CEO, Twilio) Bottom Line Up…
The Official SaaStr Podcast: SaaS | Founders | InvestorsWhy Anthropic, Cursor & FAL Ditched Traditional Sales Playbooks: The New Go-to-Market for Technical Teams and Product-Led Growth
From the SaaStr Annual / AI Summit – How three breakout AI companies rewrote the rules of enterprise sales. And see everyone at 2026 Annual + AI Summit May…
The Official SaaStr Podcast: SaaS | Founders | InvestorsB2B at Scale: Hard-Won Lessons from Cliff Obrecht on Building Canva from $0 to $4B ARR
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…
The Official SaaStr Podcast: SaaS | Founders | InvestorsThe Latest 20VC+SaaStr: Benioff Joins — And Delivers $1B+ AI Revenue; Anthropic Demand is Insatiable; AI Following Up With 1,000,000+ Leads at Salesforce
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…
The Official SaaStr Podcast: SaaS | Founders | InvestorsFrom 100M+ Free Users to $1M Enterprise Deals: The Calendly Playbook for Hybrid PLG Success - Insights from CEO Tope Awotona
When you think about Product-Led Growth (PLG) success stories, few companies exemplify the model better than Calendly. Founded in 2013 by Tope Awotona…
The Official SaaStr Podcast: SaaS | Founders | InvestorsHow Gusto Built “Gus” – Their AI Assistant Serving 400K+ Small Businesses: Lessons from the Trenches
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…
The Official SaaStr Podcast: SaaS | Founders | InvestorsThe Latest 20VC+SaaStr: Databricks Hits $100B, CoreWeave’s $11B Debt Gamble, and Why We’re All Living in the AI Bubble
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…
The Official SaaStr Podcast: SaaS | Founders | InvestorsAI Agents in B2B: Top 10 Learnings from Aaron Levie, CEO of Box and IBM's VP of AI
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…
The Official SaaStr Podcast: SaaS | Founders | InvestorsHow We Built ChatGPT Enterprise's Sales Team from Absolute Zero: The Complete Playbook with Maggie Holt, Head of GTM
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…