The Official SaaStr Podcast: SaaS | Founders | Investors

High inference costs are OK—if they make your product so viral and so competitive it almost sells itselfHere’s the counterintuitive insight that’s reshaping how the smartest AI founders think about unit economics:Your inference costs aren’t your gross margin problem. They’re your CAC replacement.The companies growing fastest right now—Cursor crossing $1B ARR with ~300 employees and no traditional marketing, Lovable hitting $300M ARR with zero paid acquisition—aren’t sweating inference costs. They’re leaning into them. They’re treating compute as their primary growth investment, not their primary ma...

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 garbage results. Then they posted about how “AI agents don’t work.”But here’s what we know after 8 months of running 20+ agents across our entire go-to-market at SaaStr — with just 3 humans and a dog: $4.8 million in additional pipeline sourced by agents. $2.4 million in closed-won revenue. Deal volume more than doubled. Win rates nearly doubled. And none of it cannibalized our existing inbound.It works. Bu...

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, and we covered a lot of ground — from the state of the SaaS market to PE exits to vibe coding to how agents are already reshaping how software gets bought and sold. I wanted to pull together the key themes here, because I think founders need to hear some of this, even if it’s uncomfortable.Let me walk through the big takeaways.1. If Growt...

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 (Partner, Innovation Endeavors) to share the whole story — and his top mistakes.And come hear 200+ stories like this at SaaStr AI Annual May 12-14 in SF Bay!!Top 5 Takeaways1. The CEO who dismissed “Backup for Salesforce” as “the dumbest idea I’ve ever heard” went on to build the category leader.Sam literally stopped a board meeting to call out how stupid he thought the idea was. Si...

Paul Adams is Chief Product Officer at Intercom, leading Product Management, Product Design, Data Science, and Research. He joined when Intercom was just a 14-person company after first advising the startup, and has been on the executive team ever since. Before Intercom, Paul held leadership, product, and UX roles at Facebook (Ads, Platform) and Google (Gmail, Docs, YouTube)—he was on Google’s mobile team when the iPhone launched. He’s the author of the best-selling book Grouped on social software design and co-hosts the podcast Intercom on Product with co-founder Des Traynor.When C...

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 revenue on a quarter-over-quarter basis. This is the roadmap.The Filevine Story: 10 Years of Grinding, Then AI Changed EverythingRyan Anderson didn’t set out to build a $3 billion legal tech company. He set out to stop waking up at 3am in a cold sweat.As a young trial lawyer in the early 2010s, Anderson was drowning. Deadlines piled up. Assignments disappeared. He’d lie awake convinced he’d m...

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 transformation journey at SaaStr AI London — and the learnings are a masterclass for any revenue leader trying to figure out how to actually deploy AI in GTM.We’re all hearing about AI-native companies crushing it. Replit, Gamma, Harvey.But what if you’re running a real B2B company? One with 400 salespeople, 15,000 customers, and years of accumulated process debt?That’s exactly where Personio was in May 2024 when the...

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 joined shortly thereafter, and after a slow few months, Kyle rocketed the org to almost $100m ARR in just a few years -- with growth accelerating at scale. Both Kyle and Jason have shared AI agents, learnings, and more on their AI agent journey and Kyle sat down with Jason on the very latest in AI for GTM. Kyle now manages a 100+ human AI-infused sales team and Jason and Amelia at SaaStr...

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. And the response was overwhelming.But here’s the thing: the #1 objection we kept hearing was “Yeah, but this won’t work for me. I don’t have your scale. I don’t have your data. I don’t have 10 years of history.”That’s simply not true.If you have customers, if you have revenue, if you have a database of any size—AI agents will...

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 engineer?Most of the anxiety I’m seeing in the market right now is based on a false narrative. A dangerous “woe...

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 workSix 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 development.The results look incredible on paper: 6.7% outbound response rates (double the industry average), $1M+ closed in 90 days from our inbound agent alone, and 20% of our event ticket sales now coming from AI.</p...

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 GiantFrom zero lines of code to 700 employees and doubling revenue annually, Datadog CEO Olivier Pomel shares the counterintuitive strategies that built one of the most customer-obsessed co...

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 venture conversation about “exciting trends.” This is three investors with $3+ billion in combined AUM telling you what’s actually working, what’s spectacularly failing, and why the old playbook...

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 AI BDRs qualifying inbound leads and nurturing prospects through our funnel* 1 AI RevOps agent tracking and managing our partner pipelineOp...

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 labor budgets instead of software budgets.Top 5 Takeaways* Transactional pricing is replacing traditional SaaS at an accelerating rate. The fundamental shift is driven by AI’s ability to complete tasks end-to-end, enabling companies to...

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 Understands Your Product During The Interview ProcessOk I know some even many w...

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 (SmartRecruiters) from pre-revenue to $100M ARR. He writes about the changing software industry in real-time at his Substack.He came to SaaStr Annual + AI Summit for a deep dive on AI and Product.Brett’s...

A SaaStr Annual + AI Summit conversation with Jesse Zhang, CEO of Decagon, and Sarah Ittelson, Partner at AccelDecagon Today: The Numbers Behind the HypeFounded 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 human support teams.The Growth Trajectory:* Founded: Late 2023* Time to Eight Figures ARR: ~18 months* Team Size: ~100 people (and scaling rapidly)* Location: 100% in-person team* Custom...

The State of AI + Software: Where It’s Going - FastThis 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 have at least 100 sales reps. Why? Because to get from $50M to $100M, you need...

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 FrontIf you’re a CMO, CRO, or founder and you haven’t deployed at least one AI agent by Halloween 2025, you’re already behind. Not “might fall behind” — you’re already behind. “Every VC I know where a startup...