SaaStr AI Annual 2026 kicks off tomorrow, May 12, at the San Mateo Event Center, and the agenda has gotten deeper, sharper, and more operator-led than at any SaaStr in our history. Three days, hundreds of sessions, and a wave of new additions we want to make sure you don’t miss before you build your schedule tonight.
Here are 20 of the newest, sharpest sessions on the calendar. Founders, CROs, CCOs, and investors getting brutally honest about what is actually working with AI agents, and what is not.
In no particular order.
1. State of the Agents | Jason Lemkin (CEO, SaaStr) + Amelia Lerutte (CAIO, SaaStr)
Thursday, May 14
The opening keynote of Day 3, and the most-requested session on the agenda. A frank, data-backed look at where agents are actually delivering ROI in B2B today, where they are still stuck in pilot purgatory, and what changes between now and the end of 2026.
2. Pilot Purgatory Is Over: Why It’s Time to Commit to Agents | Sarah Kennedy (VP Marketing, Google Cloud & Google Workspace)
Thursday, May 14
Google Cloud’s marketing leader makes the case that the pilot era is finished. If your agent is still in a slide deck instead of in production, you are already behind. A pragmatic look at how to move from “we’re evaluating AI” to “agents own this workflow.”
3. The Agent Flywheel: How to Win Distribution When AI Agents Pick the Product | Lavanya Shukla (VP Growth and AI, CoreWeave)
Thursday, May 14
What happens to GTM when the buyer is an agent, not a human. Distribution, ranking, and discoverability all change when the customer is software. The new SEO conversation, taken seriously.
4. Inside the AI Economy: What Stripe’s Data Reveals on How Top AI Companies Approach Growth, Monetization, and Agents | Maia Josebachvili (CRO of AI, Stripe)
Tuesday, May 12
Stripe powers 86% of the Forbes AI 50, so they see how the fastest-growing AI companies actually operate. Maia shares the patterns: how top AI companies monetize earlier, sell globally by default, and the role agents are starting to play in commerce.
5. The AI Investing Memo Has Changed: What Scale Is Looking for Now vs. 18 Months Ago | Rory O’Driscoll (Partner, Scale Venture Partners)
Tuesday, May 12
Rory has been writing checks since the 90s (Bill, Box, DocuSign) and has watched hundreds of AI pitches in the last two years. He breaks down exactly what has changed in the AI investment memo: the metrics that matter now that real usage data exists, the categories that are overfunded, and which AI companies pattern-match to the durable winners of past cycles.
6. AI-Native GTM 101: The 5 Calls Founders and CROs Have to Get Right | Kyle Norton (CRO, Owner.com)
Wednesday, May 13
Owner.com’s AEs produce 3x the revenue of traditional reps. Kyle walks through the five make-or-break decisions that separate AI-native GTM orgs from teams that just bolted a copilot onto a broken process: what to automate first, how comp plans need to change, and what AI-native hiring actually looks like.
7. CRO Summit: We Deployed AI Agents Across Our Sales Org. Here’s What Broke, What Worked, and What We’d Do Differently | Philip Lacor (CRO, Personio), Ghazi Masood (CRO, Replit), Jennifer Lawrence (CRO, Red Panda)
Tuesday, May 12
Three CROs from three very different stages, all post-deployment, telling the truth about what blew up the first time they shipped agents into a real sales org. The most useful conversation for any sales leader who has stopped asking “should we” and started asking “how.”
8. CRO Summit: Comp Plans, Headcount, Margins. What Changes in Sales When AI Delivers the Outcome | Sam Blond (Co-Founder & CEO, Monaco)
Tuesday, May 12
If an agent books the meeting, qualifies the lead, and writes the follow-up, who gets paid? The first session at SaaStr to seriously work through the comp, headcount, and margin math of AI-delivered outcomes.
9. I Was a VC at Founders Fund. I Saw 200 AI Sales Startups. Then I Built My Own. Here’s What Everyone Gets Wrong | Sam Blond (Co-Founder & CEO, Monaco)
Wednesday, May 13
A founder who saw 200 AI sales pitches from inside Founders Fund, then went and built one. The pattern of what every deck got wrong, and the small number of things that actually predicted which AI sales companies would scale.
10. Your AI Agent Will Get You Sued. Here’s How We Fixed Ours | Sivanne Fishel (VP Client Success, Papaya Global) + Hagit Ben-Tzur (Director of Product Experience, Papaya Global)
Thursday, May 14
Papaya Global ships agents into HR and global payroll, where a single hallucination is a regulatory event in 160 countries. The session every product leader putting agents in front of customers needs to attend before legal forces them to.
11. Nobody Wants More AI Chat: How We Built AI That Grew Our Revenue 78% YoY and Performs Real Work Across HR, IT, and Finance | Luke Prokopiak (Product Lead, Rippling)
Wednesday, May 13
Most AI in workforce software stops at the chat window. Rippling shows a live walkthrough of agents that take a business question, ground the answer in the company’s Employee Graph, and stage real operational work for review and approval. The shift from chat to action, with a real revenue number attached.
12. Stop Buying AI Chatbots: Build Your Own Internal Assistant | Simon Farshid (CEO, Assistant-UI)
Wednesday, May 13
A direct counter to the “buy a vendor chatbot” reflex. When the build is genuinely cheaper, faster, and better, and a working framework for deciding which side of that line your use case sits on.
13. What AI-Powered GTM Actually Looks Like: What Happens When Marketing Leaders Go All-In on AI | Denise Persson (CMO, Snowflake) + Amelia Lerutte (CAIO, SaaStr AI)
One runs marketing for a $50B+ public company with a team of 700. The other runs AI across SaaStr with 30+ agents in production. Both have stopped talking about AI-powered GTM and started actually running it. Not a panel about what marketing could look like with AI. Two operators comparing notes on what they have deployed, what is working, what flopped, and what they are building next.
14. From Prompt to Revenue: How AI Agents Are Rewriting the Commerce Stack | Adam Mawdesley (CRO, Shoplazza)
Thursday, May 14
Commerce was already being rewritten by AI search and AI shopping agents. Adam walks through what that means for merchants, conversion, and the next generation of the commerce stack.
15. Why Connected AI Agents Win More Deals: A Live Walkthrough of Agentforce Sales + Slack in Action | Christina Hastings (Product Marketing, Agentforce Sales Lead, Salesforce)
Wednesday, May 13
A live walkthrough, not a demo deck. Salesforce shows connected agents doing top-of-funnel research, eliminating the pre-call scramble in Slack, and replacing manual CRM work with conversational prompts. The clearest picture yet of what “connected agents” actually means in production.
16. AI Agents 101: How to Deploy Your Own Digital Clone or Agent (Bring Your Laptops!) | Jason Lemkin (CEO & Founder, SaaStr AI)
Tuesday, May 12
Jason spends $500K a year on AI tools and built one that beats most of them in 25 seconds for $0.20. A live, on-stage build of an internal AI VP of Marketing, no engineering background required. Bring a laptop, leave with an agent.
17. FDE (CCO) Summit: The Game Changed. 5 Counterintuitive Moves for Building Customer Success in AI Hypergrowth | Monica Perez (Head of Customer Success, Lovable)
Wednesday, May 13
Lovable is one of the fastest-growing AI companies in the world, and their head of CS is rewriting the CSM playbook in real time. Five moves that look wrong on paper and are working in practice.
18. FDE (CCO) Summit: Your Customers Don’t Need a CSM. They Need an Engineer | Ryan Seams (VP Customer Solutions, AssemblyAI)
Wednesday, May 13
The Forward Deployed Engineer model is taking over customer success at AI-native companies. Ryan on what changes when the customer needs implementation help, not a quarterly business review.
19. FDE (CCO) Summit: 7 Metrics for the AI Era. How to Measure Success When Software Delivers Outcomes, Not Features | John Gleeson (Founder & General Partner, Success Venture Partners)
Wednesday, May 13
NRR, GRR, and logo retention were built for a feature-based world. When software delivers outcomes, the scorecard changes. Seven new metrics for the AI era from one of the most respected operators in customer success.
20. The State of Vertical AI: Opportunities, Threats, and What It Actually Takes to Win | Jeremy Kaufmann (Partner, Scale Venture Partners) + operators from Inspiren and GC AI
Thursday, May 14
Foundation model companies are pushing into legal, health, and every vertical in between. Investors and operators inside legal and health AI on whether vertical AI moats are real, where the value lives, and what it actually takes to win when GPT-6 ships in your category.
Plus the Pitch Comp, the Vibe Coding MasterClass, and the Influencer Track
Honorable mentions worth a slot on your schedule:
- Vibe Coding MasterClass with Replit. Live builds Wednesday and Thursday, in front of the room.
- SaaStr AI 2026 Pitch Comp. 20+ top startups across all three days. The first time you’ll see Plexe AI, Personal AI, Cardinal, Opsin, Phinite, Pebble, Qodex, Yolk, Scalestack and others on a SaaStr stage.
- Building a 1B View Influencer Program (Powered by AI) with Koby Conrad, CEO & Founder, Sunflower. For any marketing leader who has been told to “do influencer” without a real playbook.
See You at the San Mateo Event Center Tomorrow
The full agenda, with every speaker, room, and session time, is at SaaStAiAnnual.com
If you haven’t grabbed a pass yet, May 12-14 in San Mateo is the most concentrated week of B2B + AI operator content on the calendar this year. We will see you there.
