The Official SaaStr Podcast: SaaS | Founders | Investors

SaaStr 838: The Present and Future of AI in Sales and GTM with SaaStr's CEO and Owner's CRO
Jason Lemkin on Going All-In on AI Agents: 20 Agents, Zero SDRs, and the Death of Mid-Pack Sales
Jason Lemkin, Founder and CEO of SaaStr, sits down with Kyle Norton, CRO at Owner, to share the raw story of how frustration with sales team turnover pushed him to deploy 20 AI agents in under a year, and why we'll never go back.
In this episode, we cover:
→ Why Jason stopped hiring SDRs after two senior reps ghosted him right before SaaStr Annual → The real reason most AI agent deployments fail (hint: it's not the technology)
→ How to pick your first AI vendor: "Talk to your forward deployed engineer before you sign"
→ Why Salesforce is having a Renaissance as the hub for AI agents
→ The brutal truth about mid-pack sales jobs being in "terminal decline"
→ How to get started with AI agents when your CFO won't give you budget
→ AgentForce vs. the hot startups: what actually works in production
→ Why the $250K SDR is coming, but only for the truly elite
Jason's advice for revenue leaders: "Roll up your sleeves. If you haven't trained an agent yourself, you'll be utterly ignorant in the age of AI."
🔗 See the AI agents SaaStr uses: saastr.ai/agents
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This episode is Sponsored in part by HappyFox:
Imagine having AI agents for every support task — one that triages tickets, another that catches duplicates, one that spots churn risks. That'd be pretty amazing, right? HappyFox just made it real with Autopilot. These pre-built AI agents deploy in about 60 seconds and run for as low as 2 cents per successful action. All of it sits inside the HappyFox omnichannel, AI-first support stack — Chatbot, Copilot, and Autopilot working as one. Check them out at happyfox.com/saastr
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Hey everybody, the biggest B2B + AI event of the year will be back - SaaStr AI in the SF Bay Area, aka the SaaStr Annual, will be back in May 2026. 
With 68% VP-level and above, 36% CEOs and founders and a growing 25% AI-first professional, this is the very best of the best S-tier attendees and decision makers that come to SaaStr each year.  
But here's the reality, folks: the longer you wait, the higher ticket prices can get. Early bird tickets are available now, but once they're gone, you'll pay hundreds more so don't wait. 
Lock in your spot today by going to podcast.saastrannual.com to get my exclusive discount SaaStr AI SF 2026. We'll see you there.

SaaStr 837: 10 Things To Do Right Now  to Become AI Native with Filevine's CEO & Founder
Ryan Anderson, Co-Founder and CEO of Filevine, shares the playbook for how his legal tech company successfully transitioned from a traditional SaaS business to an AI-native company, now generating more new revenue from AI products than their core SaaS platform.
With 6,000 customers, 700 employees, and $200M+ ARR growing at nearly 60%, Filevine has cracked the code on AI transformation. Ryan breaks down the strategic, technical, and cultural changes required to make the shift.
div]:bg-bg-000/50 [&_pre>div]:border-0.5 [&_pre>div]:border-border-400 [&_.ignore-pre-bg>div]:bg-transparent [&_.standard-markdown_:is(p,blockquote,h1,h2,h3,h4,h5,h6)]:pl-2 [&_.standard-markdown_:is(p,blockquote,ul,ol,h1,h2,h3,h4,h5,h6)]:pr-8 [&_.progressive-markdown_:is(p,blockquote,h1,h2,h3,h4,h5,h6)]:pl-2 [&_.progressive-markdown_:is(p,blockquote,ul,ol,h1,h2,h3,h4,h5,h6)]:pr-8"> _*]:min-w-0 standard-markdown"> Key Takeaways:
Nothing is Sacred – Be prepared to tear down working systems that don't serve your AI future. Use a simple framework: keep what's critical to your competitive moat and keeps you fast; eliminate what slows you down.
Content → Context – Your SaaS data becomes the competitive advantage when it serves as context for AI agents. Think Cher's closet in Clueless—you need both the organized system AND the AI.
Restructure Your Architecture – AI can't just be "sprinkled on top." Your ML team needs to own the AI data layer and iterate daily without bottlenecks.
Hire AI Natives – They want access to rich data and distribution. Sell them on what you have that AI-only startups don't.
Consider Acquisitions – Filevine acquired Parrot to jumpstart their ML capabilities. Speed matters.
Rebrand with Intent – Signal the change internally and externally. It's symbolic but powerful.
Obsess Over Usage – If you can't measure it, don't ship it. Track DAU/WAU/MAU religiously.
Leverage Your Data – Control API access, monitor AI traffic for product ideas, and don't give away your advantage for free.
Price to Dominate – Your high SaaS margins let you undercut AI-only competitors on blended gross margin.
Build One Product – Stop selling to customers who won't buy AI. Assume AI is implicit in everything you build.
About the Speaker: Ryan Anderson is the Co-Founder and CEO of Filevine, an AI-powered legal operating system. Under his leadership, Filevine has achieved 96% gross revenue retention and 124% net revenue retention while successfully pivoting to AI-native operations.
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This episode is Sponsored in part by HappyFox:
Imagine having AI agents for every support task — one that triages tickets, another that catches duplicates, one that spots churn risks. That'd be pretty amazing, right? HappyFox just made it real with Autopilot. These pre-built AI agents deploy in about 60 seconds and run for as low as 2 cents per successful action. All of it sits inside the HappyFox omnichannel, AI-first support stack — Chatbot, Copilot, and Autopilot working as one. Check them out at happyfox.com/saastr
---------------------
Hey everybody, the biggest B2B + AI event of the year will be back - SaaStr AI in the SF Bay Area, aka the SaaStr Annual, will be back in May 2026. 
With 68% VP-level and above, 36% CEOs and founders and a growing 25% AI-first professional, this is the very best of the best S-tier attendees and decision makers that come to SaaStr each year. 
But here's the reality, folks: the longer you wait, the higher ticket prices can get. Early bird tickets are available now, but once they're gone, you'll pay hundreds more so don't wait. 
Lock in your spot today by going to podcast.saastrannual.com to get my exclusive discount SaaStr AI SF 2026. We'll see you there.

SaaStr 836: The Step-By-Step Playbook for Building AI-Powered GTM Teams with Personio's CRO


Philip Lacor, CRO of Personio, shares his company's journey to building an AI-powered go-to-market motion, including 5 critical lessons learned and 4 real-world use cases delivering measurable results.
In this podcast, Philip breaks down:
✅ The 5 lessons for AI transformation: top-down + bottom-up motion, cross-functional teams, prioritization frameworks, building AI culture, and combining great stack with context
 ✅ How to build AI-powered workflows that actually work (not just more tools to test)
 ✅ Real use cases: Win/loss analysis, expansion SDR assistants, intent scoring, and AI chat
✅ Why their expansion SDRs went from 2 hours of research per day to 15 minutes while doubling pipeline per rep
✅ The truth about AI ROI: where it shows up and how long it takes
 ✅ How to get your team excited about AI (not scared of it) Philip doesn't hold back on what's working, what's failed, and what questions they still haven't answered.
If you're a CRO, founder, or GTM leader trying to figure out how to actually implement AI beyond the hype, this is the playbook. 
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This episode is Sponsored in part by HappyFox:
Imagine having AI agents for every support task — one that triages tickets, another that catches duplicates, one that spots churn risks. That'd be pretty amazing, right? HappyFox just made it real with Autopilot. These pre-built AI agents deploy in about 60 seconds and run for as low as 2 cents per successful action. All of it sits inside the HappyFox omnichannel, AI-first support stack — Chatbot, Copilot, and Autopilot working as one. Check them out at happyfox.com/saastr
 
---------------------
 
Hey everybody, the biggest B2B + AI event of the year will be back - SaaStr AI in the SF Bay Area, aka the SaaStr Annual, will be back in May 2026. 
 
With 68% VP-level and above, 36% CEOs and founders and a growing 25% AI-first professional, this is the very best of the best S-tier attendees and decision makers that come to SaaStr each year.  
 
But here's the reality, folks: the longer you wait, the higher ticket prices can get. Early bird tickets are available now, but once they're gone, you'll pay hundreds more so don't wait. 
 
Lock in your spot today by going to podcast.saastrannual.com to get my exclusive discount SaaStr AI SF 2026. We'll see you there.
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More from SaaStr: https://www.saastr.com
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SaaStr 835: AI + B2B in 2026: Find the Tailwinds or Get Left Behind with SaaStr CEO and Founder Jason Lemkin


Software spend is set to hit record levels in 2026, but you're not getting any of it unless you change.
SaaStr CEO and Founder Jason Lemkin breaks down the paradox facing B2B companies right now: It's never been easier to scale to $100M (for a select few), while everyone else struggles. Half of all VC dollars are going into just 4 deals. IPOs ended the year with a whimper.
And that AI copilot you built? It doesn't count.
In this session, Jason shares the data on what's actually happening and what you need to do to capture your share of the hundreds of billions flowing into software.
Key insights:
Why "seed is for suckers" in today's VC environment
The 3 types of AI products that unlock budget (and the one that doesn't)
Why 30% of new IT budget is going to AI and how to steal it
The TAM expansion math behind Cursor, Gamma, and AI SDR tools
Why copilots and AI features alone won't save you
The efficiency metrics every founder needs to track in 2026
If you didn't reaccelerate growth in 2025, you get a D. You can't get a D in 2026.
🎤 Recorded at SaaStr London AI Summit | December 2025
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This episode is Sponsored in part by HappyFox:
Imagine having AI agents for every support task — one that triages tickets, another that catches duplicates, one that spots churn risks. That'd be pretty amazing, right? HappyFox just made it real with Autopilot. These pre-built AI agents deploy in about 60 seconds and run for as low as 2 cents per successful action. All of it sits inside the HappyFox omnichannel, AI-first support stack — Chatbot, Copilot, and Autopilot working as one. Check them out at happyfox.com/saastr
 
---------------------
 
Hey everybody, the biggest B2B + AI event of the year will be back - SaaStr AI in the SF Bay Area, aka the SaaStr Annual, will be back in May 2026. 
 
With 68% VP-level and above, 36% CEOs and founders and a growing 25% AI-first professional, this is the very best of the best S-tier attendees and decision makers that come to SaaStr each year.  
 
But here's the reality, folks: the longer you wait, the higher ticket prices can get. Early bird tickets are available now, but once they're gone, you'll pay hundreds more so don't wait. 
 
Lock in your spot today by going to podcast.saastrannual.com to get my exclusive discount SaaStr AI SF 2026. We'll see you there.

SaaStr 834: Why OpenAI Doesn't Pay Sales Commission (And Why It Works) with OpenAI GTM Leader Maggie Hott, and Harry Stebbings, Founder of 20VC
Discover how OpenAI's unique approach to B2B sales compensation is changing the game. In this interview with Harry Stebbings, Founder of 20VC, Maggie Hott, OpenAI GTM leadership, shares her experience at OpenAI, including why they don't pay sales commissions, and what B2B sales leaders can learn from this disruptive model.
---------------------
This episode is Sponsored in part by HappyFox:
Imagine having AI agents for every support task — one that triages tickets, another that catches duplicates, one that spots churn risks. That'd be pretty amazing, right? HappyFox just made it real with Autopilot. These pre-built AI agents deploy in about 60 seconds and run for as low as 2 cents per successful action. All of it sits inside the HappyFox omnichannel, AI-first support stack — Chatbot, Copilot, and Autopilot working as one. Check them out at happyfox.com/saastr
---------------------
Hey everybody, the biggest B2B + AI event of the year will be back - SaaStr AI in the SF Bay Area, aka the SaaStr Annual, will be back in May 2026. 
With 68% VP-level and above, 36% CEOs and founders and a growing 25% AI-first professional, this is the very best of the best S-tier attendees and decision makers that come to SaaStr each year.  
But here's the reality, folks: the longer you wait, the higher ticket prices can get. Early bird tickets are available now, but once they're gone, you'll pay hundreds more so don't wait. 
Lock in your spot today by going to podcast.saastrannual.com to get my exclusive discount SaaStr AI SF 2026. We'll see you there.