Managing 1-2 AI agents? Easy. Managing 20+? That's a different game entirely.
After 9+ months running nearly 30 AI agents in production at SaaStr, we've learned what actually breaks at scale - and nobody's talking about it. This isn't about deployment tips or vendor selection. This is about the brutal realities that only emerge when you're juggling 20+ agents generating $1M+ in revenue.
1. The Context Switching Tax
Managing 20 agents = managing 20 employees who all speak different languages. Each needs daily 1-on-1s. The math doesn't work: 20 agents Ă 20 min = 6.7 hours/day, but you only have 3-4 hours of capacity.
2. The New Agent Blackout Period
Every new agent costs you 2 weeks of chaos. While onboarding Monaco, Artisan's response rates dropped 3% because contacts went stale. You can only safely add 1.5 agents per month max - any faster and you're running in place.
3. The AI Agent Succession Planning Crisis
You're the single point of failure for $1M+ of AI-driven revenue. Only 2-5% of your team could manage these agents. What happens when you get hit by a bus? Go on vacation? Leave the company?
4. The Agent as Truth-Teller
"You're 56% behind target. Block 3 hours tomorrow or adjust your goal." Your agents don't sugarcoat. They have all the data and they'll roast you every day. Is that helpful or demoralizing? We still don't know.
5. The Compliance/Security Drift
You ran a security audit in January. It's now February. You've shipped 40 updates. Did you re-audit? Probably not. Your security posture is degrading in real-time while you iterate at AI speed.
BONUS #6: You Lose Patience with Humans
After managing agents that respond instantly and work 24/7, humans feel painfully slow. "What do you mean you don't know the answer? My agent knows instantly." This makes you worse at managing actual people.
Sales/Outbound: Artisan, Monaco, Agent Force
Inbound: Qualified
RevOps: Momentum, Attention
Marketing: 10K (custom AI VPM), Gamma, Opus Pro
Customer Support: HappyFox
Internal: SaaStr Sponsors portal (custom vibe-coded)
Amelia Lerutte - Chief AI Officer, SaaStr
Jason Lemkin - Founder & CEO, SaaStr
The uncomfortable truth: Managing 20+ agents makes you worse at managing humans. You get used to instant execution, no pushback, 24/7 availability, and perfect memory. Then humans feel... inefficient.
Maybe the future isn't "how many agents can I add" but "how deep can I go with the ones I have."
Subscribe for weekly AI deployment content from the trenches. No theory. No vendor pitches. Just what actually works (and breaks) at scale.
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Hey everybody - we are LESS THAN 90 DAYS out from the biggest B2B and AI event of the year. SaaStr Annual is coming back to the SF Bay Area this May, and if you're not registered yet, what are you waiting for?
This is where the real deals get done. 68% VP-level and above. 36% CEOs and founders. 25% AI-first professionals. This isn't a conference, this is THE room where S-tier decision makers show up to figure out what's next.
But here's the deal: ticket prices go up FAST. Like, actually hundreds. Don't be that person who waits and then pays full price.
Lock in your spot TODAY. Go to podcast.saastrannual.com and use my exclusive discount for SaaStr AI SF 2026.
May is closer than you think. See you there.
---------------------
This episode is Sponsored in part by HappyFox:
Imagine having AI agents for every support task â one that triages tickets, another that catches duplicates, one that spots churn risks. Thatâd 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 â Chatbot, Copilot, and Autopilot working as one. Check them out at happyfox.com/saastr
SAASTR 843: Software Stocks Have Massively Crashed. Here's What Founders Need to Know.
SaaStr founder and CEO Jason Lemkin joins the TBPN show for a wide-ranging conversation on the state of SaaS, AI, and venture capital.
Jason shares how he shrunk his team from 15 to 3 people by going all-in on AI agents, why he's lost patience with companies that haven't re-accelerated growth, and the real economics behind running large-scale events. He breaks down why PE has "said goodbye to B2B," how vibe coding is flooding the market with competitors, and what's making the IPO window both exciting and treacherous. Plus: why the agent that closed a $100K deal on a Saturday night matters more than any demo day pitch, and how AI discoverability is quietly reshaping how businesses choose their software stack.
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This episode is Sponsored in part by HappyFox:
Imagine having AI agents for every support task â one that triages tickets, another that catches duplicates, one that spots churn risks. Thatâd 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 â 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 842: The 90/10 Rule for AI Agents: What to Build vs Buy with SaaStr's CEO and CAIO
SaaStr's Chief AI Officer, Amelia Lerutte, and SaaStr CEO & Founder Jason Lemkin break down SaaStr's evolving 90/10 rule for AI agents and apps: buy 90% off the shelf, build the 10% you can't find.
In this episode, they walk through two recently built tools: an internal AI VP of Marketing and an external-facing customer portal, and share the real trade-offs of deploying vibe coding apps into production.
Topics covered:
Why we replaced a paid SaaS tool with a vibe-coded app (and what pushed us over the edge) How Claude Cowork changed the game for building more complex apps
The role of writing a spec before vibe coding
Tackling single sign-on as a non-engineer
How we used Cowork to process 150+ customer contracts in hours instead of days
Lovable's data on what people are actually vibe coding
Maintenance costs and the hidden time suck of custom apps
Why zero AI in your product should scare you
The "jaw drop" test for SaaS products in 2026
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Tools & resources mentioned: Replit, Claude Cowork, Clerk, Lovable, Zapier, Salesforce, Monaco
đ See all the AI agents and tools we use: saastr.ai/agents
đ SaaStr Annual 2026 (May 12-14): saastrannual.com
đď¸ 20VCwith Harry & Jason & Rory: Drops every Thursday
#SaaStr #AI #VibeCoding #B2BSaaS #AIAgents #BuildvsBuy
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This episode is Sponsored in part by HappyFox:
Imagine having AI agents for every support task â one that triages tickets, another that catches duplicates, one that spots churn risks. Thatâd 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 â 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 841: Going From Blobs to Billions. Clay's Co-Founder Breaks Down Inbound, Outbound, and AI-Powered Sales.
Clay's Co-Founder Varun Anand takes the stage at SaaStr to break down how the company went from paying for claymation blobs before generating any revenue to powering growth workflows for companies like Cursor, Anthropic, and Figma. He explains why brand has always been core to Clay's identity, how their CFO roast videos and creative campaigns are actually capturing mindshare in a world where B2B marketing is painfully boring, and why he pushes back on the "use AI for everything" mentality that's taken over the industry.
Varun does a full live demo building an inbound qualification workflow from scratch using real audience volunteers, walking through everything from lead enrichment and waterfall data sourcing to AI-powered scoring, personalized meme generation, research brief creation, and CRM updates. He also brings audience members on stage to do live growth hacking for their actual business problems.
Beyond the product, this session goes deep on hiring. Varun shares the origin story of the GTM Engineer role, how it went from an internal job title for Clay's non-traditional sales team to the most in-demand position in B2B SaaS, and what he actually looks for when evaluating candidates (hint: it's creativity, not a traditional sales background). He talks about Clay's take-home process, work trials, why they hire generalists who commit to specific roles, and the surprising backgrounds of some of their best hires.
Whether you're building out your go-to-market motion, thinking about how to use AI without losing what makes your brand unique, or just trying to figure out what a GTM Engineer actually does, this session covers it all.
---------------------
This episode is Sponsored in part by HappyFox:
Imagine having AI agents for every support task â one that triages tickets, another that catches duplicates, one that spots churn risks. Thatâd 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 â 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 840: From 1 Agent to 20+: The Reality of Managing Multiple AI Agents Across Your GTM with SaaStr's CEO and CAIO
Eight months and 20+ AI agents later, what does managing a multi-agent GTM stack actually look like day to day?
SaaStr's CEO and Founder, Jason Lemkin, and SaaStr's Chief AI Officer, Amelia Lerutte, get candid about what's working, and what's not.
$4.8M in additional pipeline later, AI agents deployed across Go To Market have helped deal volume doubled and win rates double. But here's what nobody talks about on LinkedIn: the 15-20 hours per week each spent maintaining agents, the messy flows holding it all together, and why you still can't outrun your own AI.
They cover the 90/10 build vs. buy rule, why hyper-segmentation is the key to AI SDR success, what to demand from vendors before signing, and why bad context will always produce bad emails, whether a human or an AI writes them. Plus, they walkthrough how they built SaaStr's custom AI VP of Marketing agent to plan and execute every campaign for the year, grounded entirely in data.
If you've deployed your first agent and are thinking about what comes next, or you're skeptical the whole thing works at all, this one's for you.
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This episode is Sponsored in part by HappyFox:
Imagine having AI agents for every support task â one that triages tickets, another that catches duplicates, one that spots churn risks. Thatâd 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 â 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 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:
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This episode is Sponsored in part by HappyFox:
Imagine having AI agents for every support task â one that triages tickets, another that catches duplicates, one that spots churn risks. Thatâd 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 â 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 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:
â Why Jason stopped hiring SDRs after two senior reps ghosted him right before SaaStr Annual â The real reason most AI agent deployments fail (hint: it's not the technology)
â How to pick your first AI vendor: "Talk to your forward deployed engineer before you sign"
â Why Salesforce is having a Renaissance as the hub for AI agents
â The brutal truth about mid-pack sales jobs being in "terminal decline"
â How to get started with AI agents when your CFO won't give you budget
â AgentForce vs. the hot startups: what actually works in production
â 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."
đ 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 â one that triages tickets, another that catches duplicates, one that spots churn risks. Thatâd 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 â 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.
Key Takeaways:
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.
---------------------
This episode is Sponsored in part by HappyFox:
Imagine having AI agents for every support task â one that triages tickets, another that catches duplicates, one that spots churn risks. Thatâd 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 â 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:
â 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
â How to build AI-powered workflows that actually work (not just more tools to test)
â Real use cases: Win/loss analysis, expansion SDR assistants, intent scoring, and AI chat
â Why their expansion SDRs went from 2 hours of research per day to 15 minutes while doubling pipeline per rep
â The truth about AI ROI: where it shows up and how long it takes
â 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 â one that triages tickets, another that catches duplicates, one that spots churn risks. Thatâd 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 â 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.
---------------------
More from SaaStr: https://www.saastr.com
đş Subscribe for more AI & SaaS insights
#AIinSales #GTM #SaaStr #AIAgents #SalesAI #RevenueOperations
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:
If you didn't reaccelerate growth in 2025, you get a D. You can't get a D in 2026.
đ¤ 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 â one that triages tickets, another that catches duplicates, one that spots churn risks. Thatâd 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 â 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 OpenAIâs 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 donât 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 â one that triages tickets, another that catches duplicates, one that spots churn risks. Thatâd 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 â 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 â one that triages tickets, another that catches duplicates, one that spots churn risks. Thatâd 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 â 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 â one that triages tickets, another that catches duplicates, one that spots churn risks. Thatâd 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 â 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
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This episode is Sponsored in part by Salesforce:
Connect data, automate busywork and empower teams like nobodyâs 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 â one that triages tickets, another that catches duplicates, one that spots churn risks. Thatâd 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 â 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 nobodyâs 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 â one that triages tickets, another that catches duplicates, one that spots churn risks. Thatâd 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 â 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
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This episode is Sponsored in part by Salesforce:
Connect data, automate busywork and empower teams like nobodyâs business with the one platform that grows with you, every step of the way. Learn how Salesforce works for Startups at salesforce.com/smb.
---------------------
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.
SaaStr 828: The AI Revolution in B2B: Insights from SaaStr CEO Jason Lemkin and SaaStr Chief AI Officer Amelia Lerutte, and Qualified's CEO Kraig Swensrud
Join Kraig Swensrud, founder and CEO of Qualified, as he sits down with Jason Lemkin, CEO & Founder SaaStr, and Amelia LeRutte, Chief AI Officer at SaaStr.
In this insightful discussion, they explore the current landscape of AI in business, including the challenges and opportunities of integrating AI agents into companies. From the importance of training to the pressures of staying ahead in AI adoption, this conversation offers actionable advice for both startups and established enterprises looking to innovate. Get ready to dive deep into the transformative power of AI in the go-to-market strategies and beyond.
---------------------
This episode is Sponsored in part by Salesforce:
Connect data, automate busywork and empower teams like nobodyâs 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 Intercom:
Fin is the #1 AI Agent for resolving complex queries like refunds, transaction disputes, and technical troubleshootingâall with speed and reliability. See how Fin can deliver the highest resolution rates and highest-quality customer experience at fin.ai/saastr.
---------------------
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.
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.
---------------------
This episode is Sponsored in part by Salesforce:
Connect data, automate busywork and empower teams like nobodyâs 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 Intercom:
Fin is the #1 AI Agent for resolving complex queries like refunds, transaction disputes, and technical troubleshootingâall with speed and reliability. See how Fin can deliver the highest resolution rates and highest-quality customer experience at fin.ai/saastr.
---------------------
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.
In this comprehensive session, SaaStr CEO and Founder Jason Lemkin dives into the latest trends and developments in AI, particularly in the go-to-market (GTM) sector. The session outlines how innovative AI tools are transforming businesses, from AI SDRs and BDRs to forward-deployed engineers. Leaders in the industry are pushing the boundaries, showing higher growth rates and superior marketing efficiency. We also discuss the importance of hands-on deployment and training of AI tools to achieve success, and analyze the current and future impact of AI on B2B companies. Tune in for detailed insights and learn how to stay ahead in the rapidly evolving world of AI.
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â¨â¨This episode is Sponsored in part by Salesforce:â¨â¨
Connect data, automate busywork and empower teams like nobodyâs 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 Intercom:â¨
Fin is the #1 AI Agent for resolving complex queries like refunds, transaction disputes, and technical troubleshootingâall with speed and reliability. See how Fin can deliver the highest resolution rates and highest-quality customer experience at fin.ai/saastr. ---------------------
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.
SaaStr 825: How the AI Era Has Directly Impacted Marketing and Sales with Snowflakeâs CMO and Founding CRO
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This episode is Sponsored in part by Salesforce:
Connect data, automate busywork and empower teams like nobodyâs 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 Intercom:â¨
ďżź
Fin is the #1 AI Agent for resolving complex queries like refunds, transaction disputes, and technical troubleshootingâall with speed and reliability. See how Fin can deliver the highest resolution rates and highest-quality customer experience at fin.ai/saastr.
---------------------
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.
SaaStr 824: VC in the AI Era - Exactly What's Getting Funded, Why & When with SaaStr CEO and Founder Jason Lemkin
---------------------
This episode of the SaaStr podcast is Sponsored by Salesforce:
Connect data, automate busywork and empower teams like nobodyâs 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 of the SaaStr podcast is Sponsored by Intercom:
ďżź Fin is the #1 AI Agent for resolving complex queries like refunds, transaction disputes, and technical troubleshootingâall with speed and reliability. See how Fin can deliver the highest resolution rates and highest-quality customer experience at fin.ai/saastr.
---------------------
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.
SaaStr 823: Is GTM Really Dead?! with SaaStr CEO Jason Lemkin
In this episode, Jason Lemkin, SaaStr CEO and Founder, addresses common misconceptions about traditional go-to-market strategies in the age of AI. Despite claims that outbound marketing, SEO, and old-school tactics are dead, the speaker highlights how leading AI companies are successfully employing these methods with minor tweaks. Drawing from the success stories of OpenAI, Notion, Dialpad, and others, the presenter emphasizes the importance of high-quality content, dynamic sales tactics, and the unmatched potential of AI-driven tools like AI SDRs. He also discusses the necessity of providing substantial ROI from day one and urges marketers to reassess and improve their strategies rather than dismiss them as obsolete. Finally, practical advice is given on optimizing sales and marketing efforts to tap into the booming AI budget effectively.
This episode is sponsored by:
Fin is the #1 AI Agent for resolving complex queries like refunds, transaction disputes, and technical troubleshootingâall with speed and reliability. See how Fin can deliver the highest resolution rates and highest-quality customer experience at fin.ai/saastr.
This episode is sponsored by:
You didnât create a startup to run a small business. Let Salesforce help you connect data, automate busywork and empower employees on the only platform youâll ever need, no matter how big you get. With smarter AI and built-in collaboration tools like Slack, the skyâs the limit. Learn how Salesforce works for startups at salesforce.com/smb.
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 while you still can by going to podcast.saastrlondon.comSaaStr 822: SaaStr's Top 10+ AI Agents: AI SDR, AI BDR, AI RevOps + More: The How, The Who, The Why with SaaStr CEO Jason Lemkin
Join us in this comprehensive deep dive into the use of AI agents within SaaStr's operations, as requested by many of our followers.
Led by SaaStr CEO and Founder, Jason Lemkin, and SaaStr Chief AI Officer, Amelia Lerutte, we'll detail our journey from having no AI at the start of the year to utilizing 20 different AI agents, including 11 core ones that we rely on daily.
Learn from our insights on our most utilized AI agents, their workings, actual data, and how we manage them for optimal results. Discover specific tools like Artisan, Qualified, Gamma, and Replit, and understand how they're integrated into our outbound, inbound, and sales processes.
This episode also covers how we've internally developed AI-powered solutions for speaker application reviews, content review, startup valuation, and more. If you're interested in bringing intelligent automation to your business, this session offers practical advice and firsthand experiences to guide you on your AI journey.
--------------------- This episode is brought to you by Intercom:
Fin is the #1 AI Agent for resolving complex queries like refunds, transaction disputes, and technical troubleshootingâall with speed and reliability. See how Fin can deliver the highest resolution rates and highest-quality customer experience at fin.ai/saastr.
---------------------
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.
SaaStr 821: Swapping Stories - Building AI-First Companies: Insights from Zapierâs CEO and Co-Founder Wade Foster
Join us for an in-depth conversation with Wade Foster, co-founder and CEO of Zapier, on the SaaStr AI Swapping Stories Podcast! Wade shares how Zapier is leading the way in AI-powered automation, the evolution from simple workflows to agentic systems, and why AI fluency is now a must-have for every new hire.
In this episode, we discuss:
Whether youâre a founder, operator, or just curious about the future of work, this episode is packed with actionable insights and inspiration.
And see you at Zapconnect next week (sign up here - it's free.)
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ďżź Fin is the #1 AI Agent for resolving complex queries like refunds, transaction disputes, and technical troubleshootingâall with speed and reliability. See how Fin can deliver the highest resolution rates and highest-quality customer experience at fin.ai/saastr.
---------------------
If you're serious about B2B and AI, you need to be in London this December 2nd and 3rd. 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.
SaaStr 820: The Complete Guide to Vibe Coding Without a Developer with SaaStr CEO and Founder Jason Lemkin
Join us in this episode as we dive into the world of vibe coding with a prosumer approach. SaaStr CEO and Founder Jason Lemkin shares his extensive journey of building production-ready applications without a developer, using platforms like Replit and Lovable. From initial excitement to hard-earned lessons, learn about the strengths, challenges, and key takeaways from creating and deploying vibe-coded apps. Discover why the hype around 'building an app in 20 minutes' is often misleading, and understand the importance of thorough planning, competitive research, and mastering your platform. Whether you're a founder, aspiring app creator, or tech enthusiast, this episode will provide valuable insights into the future of no-code and low-code development.
----------------------- This episode is sponsored by Intercom
ďżź Fin is the #1 AI Agent for resolving complex queries like refunds, transaction disputes, and technical troubleshootingâall with speed and reliability. See how Fin can deliver the highest resolution rates and highest-quality customer experience at fin.ai/saastr.
---------------------
If you're serious about B2B and AI, you need to be in London this December 2nd and 3rd. 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 podcast.saastrannual.com to get my exclusive discount SaaStr AI SF 2026. We'll see you there.