The Official SaaStr Podcast: SaaS | Founders | Investors

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 packed with founders, CROs, and marketers who all seemed to be wrestling with the same existential questions: Is inbound dead? Is the GTM playbook broken? Will AI agents replace my entire team? Should I just give up and become a forward deployed...

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 Six months ago, we had essentially zero AI SDRs at SaaStr. Today, we’re running five specialized AI agents that have sent nearly 20,000 outbound messages, closed over $1M in revenue, and fundamentally changed how we think about sales develop...

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 Olivier Pomel, founder CEO of Datadog, joined us as they crossed $100,000,000 ARR in a candid conversation it would be harder to do today post-IPO. The First $100,000,000 ARR at Datadog: How Olivier Pomel Built a Customer-Centric Monitoring...

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 Lemkin, and Rory O’Driscoll dissect why even Sequoia is making dramatic leadership changes, why seed investing at $50M pre-money might not work anymore, and what it actually takes to build venture returns in the age of AI. This isn’t your typical...

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 marketing stunt, but as core members of our revenue and operations team. The lineup looks like this: Revenue Team: * 3 AI SDRs handling each of ticket inquiries, sponsor outreach, and sales support (these are different workflows, training, etc) * 2...

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 from the front lines of AI-first product pricing, exploring why traditional SaaS models are declining in favor of transactional pricing, how to choose the right pricing structure for your business, and strategies for capturing value from labo...

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 wrong VP of Sales can set you back a year — or longer. So I thought I’d come back to the classic topic and make a list of the Top 10 Mistakes I See Founders Make When Hiring a VP of Sales: #1. Hiring a VP of Sales Who Never Really Understan...

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 Salesforce.com, where he built go-to-market, launched the AppExchange, and helped scale the company from its earliest days. Previously, he worked at Siebel Systems (the fastest-growing software company of its era) and ran a B2B startup (SmartRecr...

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 Founded in late 2023—just months after GPT-4’s release—Decagon has become one of the fastest-growing AI companies in history. The company builds AI customer service agents for large enterprises, automating conversations that previously required...

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 talking to a founder recently who’s running at $50 million ARR. Classic SaaS guy turned AI guy. And he’s going to scale from $50M to $100M with just five sales reps and a team of AI agents. In the old days, at $50 million, you’d probably ha...

A deep dive into the playbook, lessons learned, and brutal truths about deploying 20+ AI agents into production — that actually work. During Dreamforce Jason (CEO) and Amelia (Chief AI Officer) at SaaStr dropped by Qualified’s office for a deep dive on its AI Agents and top learnings with Kraig Swensrud (Founder & CEO, Qualified) The Bottom Line Up Front If you’re a CMO, CRO, or founder and you ha...

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 that I’m now “Replit Fluent”. What does that mean? It’s a state where I know how to vibe well enough (without a developer), and I know the app and its capability and limits well enough, that I can basically see any app I want to build in my...

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. Marchelle brings a unique perspective to vertical SaaS sales—she’s a former hairdresser and salon owner who transitioned into SaaS sales leadership. At Mangomint, she leads sales for a deep vertical SaaS platform serving salons and spas. Her j...

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 changed. After analyzing 1,000 VC pitch decks and calculating 400,000+ startup valuations on SaaStr.ai , and having countless conversations with both sides of the table, the data is unambiguous: traditional paths to venture funding have essential...

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 at SaaStr AI London, Dec 1-2!! More here . Bottom Line Up Front The classic venture playbook is almost … no more. * Traditional SaaS metrics like burn multiples—once the gold standard for evaluating capital efficiency—are being rendered obso...

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 Partnerships Bootcamp: How to Land, Scale, and Win with Linear, Omni, Theory Ventures, and Vesey Ventures. * Christina Cordova – Chief Operating Officer at Linear, the purpose-built tool for planning and building products. Previously spent 7.5 ye...

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 human at it * How our new SaaStr.ai Startup Valuation Calculator processed 300,000+ AI startup valuations in less than 30 days. And how disruptive (and just plain cool) the new Replit v3 is. At SaaStr, we’ve gone from having essentially zero A...

Harry, Rory and Jason are back! We’re witnessing an unprecedented capital concentration in AI with NVIDIA’s $100B OpenAI investment creating a fascinating circular money machine, while new H-1B visa fees threaten startup talent acquisition and the venture funding landscape shifts dramatically toward mega-rounds for a tiny number of companies. The era of “founder friendly” has become somewhat hollo...

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 finding secret hacks or silver bullets. They don’t last or scale. It’s about mastering fundamental principles and being willing to reinvent yourself every six months to a year as you scale. Gaurav Agarwal , COO of ClickUp came to SaaStr Annual + A...

The technical and product insights from Dara Ladjevardian’s AI cloning experiment at SaaStr Annual + AI Summit . The Clone Performance Reality Check When Dara Ladjevardian, CEO of Delphi.ai, ran 1 million simulated conversations with digital versions of Brian Halligan (Chairman and founding CEO HubSpot), Lenny Rachitsky , Keith Rabois and Jason Lemkin, the most interesting findings weren’t about t...

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 Front Rory O'Driscoll: Tesla's trillion-dollar pay package for Elon is a board betting everything on doubling down - they believe without him, the stock drops 75% overnight. It's intellectually coherent but terrifying risk concentration. Jason...

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 12-14 2026 and SaaStr AI London Dec 2-3! Speaker Bios Talia Goldberg – Partner, Bessemer Venture PartnersTalia leads AI investments at Bessemer and has been at the forefront of understanding how AI companies break traditional SaaS metrics and b...

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...