SaaStr 839: Why Most SaaS Companies Will Fail at AI (And How to Avoid It) with Intercom's CPO

The Brutal Truth About Transforming a SaaS Company into an AI Company

Intercom's Chief Product Officer, Paul Adams, shares the unfiltered story of how they transformed from a struggling SaaS company with 5 quarters of declining growth into an AI-first company with a breakthrough product (Fin) that now handles 1M+ customer resolutions per week.

What You'll Learn:

• Why AI transformation requires "refounding" your entire company - not just adding AI features
• The self-harming decisions you must make to win (including parting ways with ~33% of your team)
• How to go from 0 to 6,000+ AI customers with 65% average resolution rate
• Why demos ≠ products and the "marketing overhang" problem
• The complete shift in how you build software (empirical evaluation vs. traditional product development)
• Why designers now ship code to production at Intercom
• How the buyer has changed (hint: it's no longer just the department head)

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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 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

---------------------

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.

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Key Takeaways:

1. 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.
2. 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.
3. 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.
4. Hire AI Natives – They want access to rich data and distribution. Sell them on what you have that AI-only startups don't.
5. Consider Acquisitions – Filevine acquired Parrot to jumpstart their ML capabilities. Speed matters.
6. Rebrand with Intent – Signal the change internally and externally. It's symbolic but powerful.
7. Obsess Over Usage – If you can't measure it, don't ship it. Track DAU/WAU/MAU religiously.
8. Leverage Your Data – Control API access, monitor AI traffic for product ideas, and don't give away your advantage for free.
9. Price to Dominate – Your high SaaS margins let you undercut AI-only competitors on blended gross margin.
10. 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

📺 Subscribe for more AI & SaaS insights

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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.

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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 833: AI and the Death of the 2021 Sales Playbook with SaaStr CEO and Founder Jason Lemkin Join SaaStr CEO and Founder Jason Lemkin from SaaStr London as we tackle pressing topics in AI and sales during an engaging AMA session.

From discussing the evolution of inbound vs. outbound sales to detailing the transformative impact of AI on sales roles and outbound strategies, this session covers it all.

Learn about the importance of product expertise for selling AI solutions, the rise of AI SDRs, and why knowing your top three problems is crucial for effective outbound marketing. Plus, discover insights on the rapidly improving capabilities of AI agents and their implications for competitive moats. Whether you're a sales professional, marketer, or tech enthusiast, this episode is packed with actionable insights and future trends in the AI landscape.

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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 professionals, 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 832: How to Use AI to Hyper-Customize Go-To-Market at Scale with SaaStr's CEO and Chief AI Officer

In this episode from SaaStr AI London 2025, SaaStr CEO and Founder Jason Lemkin and SaaStr's Chief AI Officer, Amelia Lerutte discuss the implementation and optimization of AI SDRs within various business contexts. They focus on key AI agents used for sales processes, data aggregation, and the customization of outbound and inbound messages. Real-world results, like increased email response rates, are highlighted along with practical steps for setting up and training AI SDRs. They also offer advice on selecting the right vendors, the importance of human oversight, and leveraging AI to improve qualification and customer interactions. Key takeaways include how AI can handle more interactions consistently and efficiently and the role of AI in augmenting human sales capabilities.

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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 831: How We Use 20+ AI Agents for Marketing & Go-to-Market with SaaStr's Chief AI Officer and CEO & Founder

Join us for part two of our series on leveraging AI tools for Go-To-Market in B2B/SaaS. In this episode, SaaStr's CEO and Founder Jason Lemkin, and SaaStr's Chief AI Officer, Amelia Lerutte discuss the importance and current state of AI in marketing, highlighting their key tech stack and tools. They share their experiences and insights in utilizing these tools for creating personalized marketing collateral, automating content repurposing, and optimizing email campaigns with AI. Learn about the convergence of sales and marketing tools, the future of AI in go-to-market strategies, and how specialized AI agents can dramatically improve your outreach, lead generation, and content creation processes.

--------------------- This episode is Sponsored in part by Salesforce: Connect data, automate busywork and empower teams like nobody's business with the one platform that grows with you, every step of the way. Learn how Salesforce works for Startups at salesforce.com/smb.

---------------------

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 830: 6 Months Later, How Our AI SDRs Actually Work as AI Runs GTM with SaaStr's CEO and Chief AI Officer

In this episode, SaaStr CEO and Founder Jason Lemkin and SaaStr's Chief AI Officer, Amelia Lerutte delve into their journey of integrating AI into our go-to-market strategy over the past six months. Starting with just one AI agent before SaaStr Annual in May, we've scaled to roughly 20 core agents by November, covering various use cases across marketing, sales, customer support, and operations.

Together they discuss the specifics of our AI implementations, the tools we have deployed, including Artisan, Qualified, and Salesforce's AgentForce, and share valuable insights on their performance, benefits, and challenges. Tune in to learn about the unexpected outcomes, the time and management required, and the significant impact on our efficiency and revenue.

--------------------- This episode is Sponsored in part by Salesforce: Connect data, automate busywork and empower teams like nobody's business with the one platform that grows with you, every step of the way. Learn how Salesforce works for Startups at salesforce.com/smb.

---------------------

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

SaaStr 829: A Hands-On Guide to SaaStr's New AI Tools with SaaStr CEO and Founder Jason Lemkin

We delve into the functionalities of our SaaStr AI tools, including the AI Mentor, which has been engaged over 100,000 times, providing answers to various startup-related queries. You'll see a demonstration of how our AI VC tools, including a startup valuation calculator, pitch deck analyzer, and benchmarking tool, work effectively to help startups understand their valuations, get honest feedback on pitch decks, and connect with VCs. Additionally, explore our newly launched VC matchmaking system and other AI agents that have been integral in automating and enhancing SaaStr's operations. Experience these tools firsthand and discover how they can add value to your startup journey. Visit SaaStr.ai to access these tools for free and see the comprehensive suite of AI agents that we use. 00:00 Introduction and Overview 00:14 Exploring SaaStr AI Tools 01:15 Deep Dive into Digital Jason 04:20 AI VC Tools and Fundraising 05:26 Startup Valuation Calculator 06:07 Pitch Deck Analyzer 16:16 Benchmarking Your Startup 18:51 VC Matchmaking and Research 21:58 Conclusion and Q&A

--------------------- This episode is Sponsored in part by Salesforce: Connect data, automate busywork and empower teams like nobody's business with the one platform that grows with you, every step of the way. Learn how Salesforce works for Startups at salesforce.com/smb.

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If you're serious about B2B and AI, you need to be in London this December.

SaaStr AI London is bringing together more than 2,000 leaders and founders for two days of practical advice on scaling into the new year.

We'll have speakers flying in from OpenAI, Wiz, Clay, Intercom, and all your favorite SaaS companies, including yours truly with Harry Stebbings for a live 20VC podcast. It'll be fun, and it's all in the heart of London.

Don't miss out: get your tickets with my exclusive discount by going to podcast.saastrlondon.com

---------------------

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.