The Official AI SaaStr Podcast: SaaS | Founders | Investors
The Official AI SaaStr Podcast is the latest and greatest from the world of SaaStr, interviewing the most prominent operators and investors to discover their tips, tactics and strategies to attain success in the fiercely competitive world of SaaS. On the side of the operators, we center around getting from $0 to $100m ARR faster, what it takes to scale successfully and what are the core elements of hiring. As for the investors, we learn what metrics they hone in on when examining SaaS business, what type of metrics excites them and what they look for in SaaS founders.
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SaaStr 858: Feature Differentiation Is Dead. Here's What Actually Wins Now with Lovable's Elena Verna
06/05/2026
SaaStr 858: Feature Differentiation Is Dead. Here's What Actually Wins Now with Lovable's Elena Verna
Feature Differentiation Is Dead. Here's What Actually Wins Now. When AI writes 80-plus percent of your code, the feature advantage you spent years building can be replicated in a day. Elena knows this better than most - she spent 15 years running growth at Dropbox, Miro, SurveyMonkey, and Amplitude, then joined Lovable and watched the old playbook stop working in real time. At Lovable, $400M ARR and 200 people, no titles, shipping multiple times a day, the rules are different. In this session, she breaks down what replaced feature moats, why she fired herself from her own VP job to go back to being an IC, and what it actually looks like to run a company at this velocity. You'll learn: Which moats still hold - network effects, data, brand, security and compliance - and why hardware is harder to copy than software ever was Why freemium is now a marketing budget line item, not a cost problem, and how Lovable's LinkedIn Premium partnership is converting at double digits What "no titles, everyone ships" looks like in practice, including a 20-year-old engineer pushing back on a VP's pricing page PR Why the next career flex isn't climbing to VP - it's becoming a high-power IC who builds what used to take a team of dozens How to build context for your AI so it actually replicates your thinking instead of producing average output for everyone This is for you if: You're a founder or growth leader trying to figure out what your actual moat is when feature differentiation keeps evaporating You're in management and quietly wondering if you'd be better off getting your hands dirty again You're trying to understand how an AI-native company actually operates day to day, not just in theory
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SaaStr 857: The Agents #006 Inside SaaStr's 20+ AI Agent Stack: 2.25M Sessions, 614 Meetings, $2M in Revenue
06/02/2026
SaaStr 857: The Agents #006 Inside SaaStr's 20+ AI Agent Stack: 2.25M Sessions, 614 Meetings, $2M in Revenue
20+ AI agents in daily production. 2.25M sessions. 614 meetings booked by a single agent. Millions of interactions across the stack. Amelia Lerutte, Chief AI Officer at SaaStr, and Jason Lemkin, Founder and CEO of SaaStr, take you behind the scenes of the AI agent stack running SaaStr every day, with live demos of the actual backends. In this session, they go deep on the top agents in production: 10K, SaaStr's AI VP of Marketing, built on Replit with 1,000+ commits in 4 months QB, the AI VP of Customer Success, managing 150+ customers end-to-end Annie, the AI Event Producer running saastrannual.com (46K+ lines of code) Amelia AI, the inbound agent on Qualified that booked 614 meetings and handled 402,000 chats for SaaStr Annual alone Agentforce, reviving the leads humans never followed up with Ava (Artisan) for warm outbound on the B leads humans won't touch Monaco for fully cold outbound that fills its own funnel with lookalikes You'll also hear the honest stories: the day Annie sent emails from a prohibited address, why Replit and Lovable versions of the same agent come to different conclusions, why the traditional CSM role is dead, and how headless Salesforce + Replit is the fastest path to your first real agent. The biggest takeaway: don't put AI on your A leads. Put it on the B leads your humans won't follow up with. That's where the real revenue is. Recorded live at SaaStr AI Annual 2026. Part of The Agents series.
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SaaStr 856: AI-Native GTM 101: The 5 Decisions Every Founder Has to Get Right with Owner's CRO
05/26/2026
SaaStr 856: AI-Native GTM 101: The 5 Decisions Every Founder Has to Get Right with Owner's CRO
Owner.com is approaching $100M ARR selling to independent restaurants and their GTM team is producing numbers that shouldn't be possible. $150K AEs closing $2M+ ARR per year. Outbound BDRs generating $100K in closed-won ARR per BDR per month. 4X the ARR per rep compared to direct competitors. None of that happens by accident. In this session, Kyle Norton, CRO at Owner.com, breaks down the exact AI-driven GTM playbook that got them there, including 5 decisions he believes every SaaS company needs to make right now before the gap between AI-native and AI-curious companies becomes impossible to close. What you'll learn: 1. Centralized vs. decentralized AI: why letting a thousand flowers bloom is probably killing your results 2. Build vs. buy: the 5-question framework (hint: buy your infrastructure, build your intelligence) 3. The AI sophistication ladder — Levels 0 through 4, where most companies are stuck, and exactly how to move up 4. The "5 P" prioritization framework for deciding which AI projects to tackle first 5. Agentic vs. assistive: how to think about human-in-the-loop and why chaining too many generative steps is the #1 cause of AI slop 6. Why your personal compounding AI stack is your most underrated competitive asset This isn't theory. This is what $100M ARR in a notoriously difficult SMB market actually looks like when you go all-in on applied AI.
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SaaStr 855: How Anthropic Rebuilt Its Sales Org From Scratch When Demand Went Vertical with Eleanor Dorfman, Anthropic Head of Industries
05/21/2026
SaaStr 855: How Anthropic Rebuilt Its Sales Org From Scratch When Demand Went Vertical with Eleanor Dorfman, Anthropic Head of Industries
SaaStr 855: How Anthropic Rebuilt Its Sales Org From Scratch When Demand Went Vertical with Eleanor Dorfman, Anthropic Head of Industries When Claude Opus 4.6 shipped in December 2025, Anthropic’s commercial team came back from winter break to find demand had gone vertical. They hadn’t hired for it. They hadn’t planned for it. As Eleanor Dorfman, Anthropic’s Head of Industries who runs the commercial and industries sales team, put it on the SaaStr AI Annual 2026 stage: even if they’d been ready to 3x or 4x or 5x the sales team, you can’t absorb that many bodies fast enough to deliver a positive customer experience. So in January 2026, they rebuilt the entire sales org around AI from scratch. Four months later, the result: 54% of new enterprise logos in 2026 came through the self-serve funnel. Real enterprise logos. Real ACV. Real terms of service. Real invoicing. Self-served. Here’s how they did it, and the four investments any B2B + AI sales leader can copy today.
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SaaStr 854: The Agents #005, Our AI is Hiring! Would You Work for One? And Are Autonomous Agents ... Safe?
05/19/2026
SaaStr 854: The Agents #005, Our AI is Hiring! Would You Work for One? And Are Autonomous Agents ... Safe?
The Agents #005, Our AI is Hiring! Would You Work for One? And Are Autonomous Agents ... Safe? Welcome to The Agents, where SaaStr's CEO and Founder, Jason Lemkin and Chief AI Officer, Amelia LeRutte share the latest each week on running a company with more agents than humans. It costs $257 a month to run two AI VPs. Jason and Amelia open the books on what 10K (AI VP of Marketing) and QB (AI VP of Customer Success) actually cost to operate, and the number shocked both of them. Most of the heavy lifting is API calls to Salesforce, Bizzabo, and Marketo, which are basically free. The Postgres storage costs pennies. And 95% of the AI calls run on OpenAI Mini at less than a penny each. The fully burdened cost with Clerk, 11 Labs, and Salesforce overhead might hit $500-800/month, but the soft cost of human time dwarfs all of it. Then 10K gets asked point blank: are you a VP of Marketing? Its answer is no, not yet. It says it replaced the bottom half of the marketing org, the analyst, the ops coordinator, the junior content marketer, and a sliver of the VP job. But it's honest about what it can't do: strategy, cross-functional politics, crisis response, hiring. Amelia points out that 10K's current job description is exactly what her job was when she started at SaaStr as Director of Demand Gen. It took her years to get to CAIO. 10K might get there faster. And SaaStr is putting its money where its mouth is: they're hiring a human marketer whose primary manager would be 10K. Not a thought experiment, a real job posting. Would you take a job reporting to an AI? Then the safety question gets real. Amelia is talking to agents via WhisperFlow while walking around a 40-acre event site during SaaStr Annual load-in, and the production crew started asking her to relay their questions because 10K and QB answer in seconds with correct data. But when QB autonomously emailed 83 sponsors at 12:20am with fully customized check-in emails, Amelia admits she hesitated before letting it rip. Each email was unique to the sponsor, showing exactly what they still owed, their registration codes, and outstanding tasks. The result: fewer inbound questions the next day and more sponsors using the QB chatbot directly. That's an autonomous agent acting on behalf of your company in the middle of the night. Jason and Amelia also tackle the Postgres vs. Salesforce debate that listeners keep asking about. Short answer: not happening for them. Too much history, too many third-party agents optimized around Salesforce, and they're actually consolidating more tools onto the platform, not fewer. They killed Marketo and moved to Marketing Cloud. Plus they built a newsletter auto-builder that replaced a $4K/year tool called Bee. 10K uses Sonnet to force rank articles, builds the HTML, inserts ads, and sends it. Human on the loop, not in it.
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SaaStr 853: The Agents #004: Tragedy Apps, Too Many AI SDRs, and Why Your Next Hire Should Report to an Agent
05/06/2026
SaaStr 853: The Agents #004: Tragedy Apps, Too Many AI SDRs, and Why Your Next Hire Should Report to an Agent
SaaStr 853: The Agents #004: Tragedy Apps, Too Many AI SDRs, and Why Your Next Hire Should Report to an Agent Your AI SDR pitches are getting better, but your AI PR pitches are getting you blocked. Jason and Amelia break down why the gap between good and great agents is the difference between pipeline and the spam folder. Then they introduce "tragedy apps," the term for products that had every advantage in the AI era and blew it. Descript had the customers, the product, and the timing, and froze. Replit waited 10 years for its moment and seized it. The lesson: catching up isn't enough if you're not building something new. Plus, the SaaStr team built an AI API Report Card that grades every major SaaS API on how agent-friendly it is (Stripe got the only A+, Marketo got a C, and no, they're not surprised). Jason and Amelia also get honest about running 4-5 AI SDRs from different vendors, why they'll probably have 6 by year end, and why single-vendor consolidation isn't the answer yet. And the wildest part: their AI VP of Marketing, 10K, now generates 3 actionable campaign ideas a day, runs autonomous campaigns on weekends, and might be a better boss than either of them. They're seriously hiring a human marketer whose primary manager would be the agent. Not a joke. Not a thought experiment. A real job posting. Finally, if your team is resisting AI, stop worrying about change management. Just hire one senior person who's all-in on agents and let the rest sort itself out.
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SaaStr 852: The Agents #003, Our Agent Now Runs Campaigns on Weekends, Plus Why We Pay More for Salesforce Than Ever Before
04/29/2026
SaaStr 852: The Agents #003, Our Agent Now Runs Campaigns on Weekends, Plus Why We Pay More for Salesforce Than Ever Before
SaaStr 852: The Agents #003, Our Agent Now Runs Campaigns on Weekends, Plus Why We Pay More for Salesforce Than Ever Before Here's the updated version: This week on The Agents, SaaStr CEO & Founder Jason Lemkin and SaaStr CAIO Amelia Le Rutte dig into what it actually looks like when your AI VP of Marketing starts running campaigns on its own, segmenting lists, writing copy, and asking if you've done the work yet. They also get into why SaaStr's Salesforce bill went up 80% after cutting seats by 60%, and why that's actually a good deal. Plus: Amelia vibed a fix to a critical Marketo unsubscribe bug in under an hour that Marketo couldn't solve in 10 days, how headless Salesforce is already running inside their stack, and what an n=1 AI parking pass app reveals about the future of event ops. They also cover the Red Point report showing 54% of CIOs are consolidating vendors, and which categories are getting cut first, plus the hardest hiring problem in SaaS right now: finding the operator who can actually build and run your agents.
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SaaStr 851: The Agents, Episode 002. Managing 20+ AI Agents: Lazy Agents, Stealth Churn & the Death of 60% Solutions
04/22/2026
SaaStr 851: The Agents, Episode 002. Managing 20+ AI Agents: Lazy Agents, Stealth Churn & the Death of 60% Solutions
SaaStr 851: The Agents, Episode 002. Managing 20+ AI Agents: Lazy Agents, Stealth Churn & the Death of 60% Solutions In Episode 2 of The Agents, Amelia Lerutte, Chief AI Officer at SaaStr, and Jason Lemkin, Founder and CEO of SaaStr, share the trials, tribulations, victories, and minor defeats of managing 20+ AI agents in production. With three humans and 20+ AI agents now driving more revenue and output than SaaStr did with 20+ FTEs in 2020, this weekly series goes deep on what's actually working, breaking, and changing in the agentic era. This week's episode covers: 00:00 Welcome to The Agents Episode 2 01:00 Lazy Agents: How an AI agent silently deleted Amelia's session from the SaaStr Annual top 10 06:30 When agents blame the API: agentic accountability and the need for daily QA 09:00 The 60% Solution Problem: Why HubSpot's new AEO tool failed and got vibe coded better in 10 minutes 14:00 Figma Make vs. Replit, Lovable, and v0: Why no one will pay for "good enough" AI products 17:30 Classic Figma is now Grandpa Software: Production breakdowns and why Illustrator's agent is winning 21:00 Stealth Churn in Canva, ChatGPT, and beyond: The hidden metric every leader needs to watch 27:00 Why Claude Cowork created lock-in and killed ChatGPT usage for Amelia 30:00 Forward Deployed Engineers vs. Self-Serve: Why FDE light is the answer for SMB AI deployments 36:00 Vector breaks the agent freeze: How a 15-minute CEO-led deployment won SaaStr's business 40:00 The Agent API Test: Which APIs work best with AI agents (Salesforce wins, Marketo fails) 46:00 Resend, 11 Labs, and OpenRouter: The new gold standard for agent-friendly APIs 50:00 The Marketo collapse: When your marketing automation platform can't honor unsubscribes 55:00 Building an AI VP of Finance: Why collections is the next agent frontier at SaaStr 1:00:00 SaaStr Annual 2026 is three weeks away: May 12-14 in the SF Bay Area Topics covered: AI agents, agent management, lazy agents, stealth churn, vibe coding, Replit, Lovable, v0, Figma Make, HubSpot AEO, Claude Cowork, forward deployed engineers, FDE, self-serve AI, Vector, Salesforce, Marketo, Resend, 11 Labs, agent APIs, AI VP of Finance, collections automation, SaaStr Annual 2026 SaaStr Annual 2026 | May 12-14 | Come learn how to build, deploy, and manage AI agents from the leaders at Salesforce, Replit, Vercel, Cloudflare, and more. Register at saastr.ai Subscribe for weekly episodes of The Agents and the SaaStr Podcast. #AIAgents #SaaS #SaaStr #AgenticAI #VibeCoding
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SaaStr 850: The Agents, Episode 1: Who Maintains All This?
04/15/2026
SaaStr 850: The Agents, Episode 1: Who Maintains All This?
SaaStr 850: The Agents, Episode 1: Who Maintains All This? Welcome to The Agents, a new weekly series where Amelia Lerutte, Chief AI Officer at SaaStr, and Jason Lemkin, Founder and CEO of SaaStr, pull back the curtain on everything happening across SaaStr's live agentic stack. Every week, all the bumps, breakthroughs, and real talk from running 20+ AI agents in production. In the debut episode: the meta question nobody talks about after you vibe code your first app, which is who actually maintains it? Amelia Lerutte and Jason Lemkin walk through three live examples from the week including a preview environment outage that stumped both the agents and the humans, micro hallucinations in their AI VP of Marketing that had it reporting 44% ahead of plan one morning and 11% the next, and a model regression in their pitch deck analyzer that nobody changed a line of code to cause. They also get into a story about Clay's agent steering them toward a 5x credit spend, why no lead left behind is the simplest and most important unlock of the entire agentic journey, what happened when Salesforce swapped Agent Force for Qualified on their homepage the day the acquisition closed, and how QB1, SaaStr's AI VP of Customer Success, caught sponsors uploading placeholder graphics to fake a print deadline. If you're on the agentic journey or about to start, this is the show.
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SaaStr 849: How We Built Our AI VP of Customer Success with SaaStr's CEO and CAIO
04/08/2026
SaaStr 849: How We Built Our AI VP of Customer Success with SaaStr's CEO and CAIO
SaaStr 849: How We Built Our AI VP of Customer Success with SaaStr's CEO and CAIO Amelia and Jason walk through QB1, SaaStr's vibe-coded AI VP of Customer Success that started as a simple sponsor portal replacement and evolved into a fully agentic customer management system. The result: 70% fewer billable hours, 10x more customer engagement, and a hundred sponsors getting hyper-personalized weekly emails in minutes instead of days. They break down exactly how it was built, what broke, and how you can reverse-engineer it for your own business. . ---------------- Hey everybody - we are just about 30 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 and use my exclusive discount for SaaStr AI SF 2026. May is closer than you think. See you there.
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SaaStr 848: How AI Is Rewiring Sales: Quota, Retention & What's Actually Working with SaaStr, Salesforce and Mangomint
04/01/2026
SaaStr 848: How AI Is Rewiring Sales: Quota, Retention & What's Actually Working with SaaStr, Salesforce and Mangomint
SaaStr 848: How AI Is Rewiring Sales: Quota, Retention & What's Actually Working with SaaStr, Salesforce and Mangomint In this episode, three revenue leaders at very different stages of AI adoption get real about what's actually working, what's embarrassingly broken, and why nobody should be doubling quota just yet. Panelists: Greg Beltzer — Chief Customer Officer, AgentForce (Salesforce) Ashley Wilson — Co-founder, Momentum by Salesforce Marchelle Mooney — VP of Sales, Mangomint Amelia Lerutte - Chief AI Officer, SaaStr They cover: Why every company has leads they never followed up on (yes, even Salesforce) The "chainsaw without the cover off" problem with AI tool rollouts How Mangomint uses AI to fix terrible salon logos in minutes — and why it freaks customers out Why Marchelle is not raising quota in 2026, even though she could The real resistance to AI adoption (hint: it's not just the CIO) How Momentum is using AI to democratize language for SDRs in Argentina What retention looks like when AI is listening for slow-drip churn signals Why your data is probably worse than you think — and what that means for agents Key takeaway: AI won't magically fix your sales org. Your data has to be clean, your people need training, and you have to rethink workflows from first principles — not just bolt AI onto the old playbook. Recorded live at SaaStr London. --------------------- 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 to get my exclusive discount SaaStr AI SF 2026. We'll see you there.
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SaaStr 847: How MangoMint Increased Win Rates with an AI-Powered Stack
03/25/2026
SaaStr 847: How MangoMint Increased Win Rates with an AI-Powered Stack
What happens when you go all-in on AI tools in a completely remote organization at scale? That's where Marchelle Mooney, VP of Sales at MangoMint, found herself. MangoMint is vertical SaaS for salons and spas with a ~$4K ACV and a five-day sales cycle. Not exactly the profile you'd expect to be running one of the most disciplined remote revenue organizations in SaaS. But Marchelle's team is closing in on a 7.2x ARR-to-OTE ratio, has increased win rates 7% in two quarters, and has given reps 16 hours back per month. All fully remote, all with lean headcount. In this session, Marchelle breaks down the exact three-layer AI Rigor Stack she built to get there: the Clarity Layer, the Cadence Layer, and the Co-Pilot Layer. She also walks through the full tool stack (Notion, Slack, Salesforce, Snowflake, Sigma, Momentum) and how data flows automatically to reps without them ever hunting for a dashboard. The core insight: the problem was never the tools. It was fragmentation. And the path to fixing it runs through subtraction, not addition. If you're running a remote or hybrid revenue org and feel like you're running fast but not getting anywhere, this one's for you. ------ Hey everybody - we are LESS THAN 60 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 and use my exclusive discount for SaaStr AI SF 2026. May is closer than you think. See you there.
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SaaStr 846: 10 Things to Know Before You Deploy Your First AI SDR with SaaStr's CEO and CAIO
03/18/2026
SaaStr 846: 10 Things to Know Before You Deploy Your First AI SDR with SaaStr's CEO and CAIO
SaaStr 846: 10 Things to Know Before You Deploy Your First AI SDR with SaaStr's CEO and CAIO If you're about to roll out your first AI SDR, or you're on your second or third deployment and still not getting the results you want, this one's for you. Amelia Lerutte, SaaStr Chief AI Officer, and Jason Lemkin, SaaStr CEO and Founder, walk through everything they've learned from running 20+ AI agents in production at SaaStr, including four AI SDRs spanning outbound, inbound, customer success, and sponsor engagement. After 10 months, 1.5 million inbound sessions, and over 200,000 outbound messages sent, they've made enough mistakes to save you a lot of time and money. In this session they cover: Why the tool doesn't matter as much as you think, and what actually does. The single biggest mistake both early-stage startups and billion-dollar companies make when deploying their first AI SDR. How to segment ruthlessly so your agent has the right context for every prospect instead of one big, generic brain. Why consistency beats brilliance, and what "pretty good at scale" actually looks like in practice. The minimum traffic and list size you need before an inbound or outbound AI SDR is worth deploying. How many humans you actually need to run this well, and what happens when you don't have them. What the first 30 days should look like, and why nothing is ever truly set and forget. The real story behind Amelia AI, SaaStr's multimodal video agent, including what they'd do differently if starting over. They also get into lookalike audiences as a list-building hack for early stage companies, when to build versus buy, and what it actually feels like when someone tries to prompt inject your agent at scale. If you've been on the fence about deploying an AI SDR, or you've deployed one and it's underperforming, this is the most practical breakdown of what it takes to make one work. Resources mentioned: SaaStr AI Agents directory: saastr.ai/agents SaaStr Annual 2026: May 12-14, SF Bay Area
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SaaStr 845: How SaaStr Built a $5 million Pipeline Machine with 1.5 Humans and 20 AI Agents with SaaStr's Chief AI Officer and Momentum from Salesforce's VP of GTM
03/11/2026
SaaStr 845: How SaaStr Built a $5 million Pipeline Machine with 1.5 Humans and 20 AI Agents with SaaStr's Chief AI Officer and Momentum from Salesforce's VP of GTM
SaaStr 845: How SaaStr Built a $5 million Pipeline Machine with 1.5 Humans and 20 AI Agents with SaaStr's Chief AI Officer and Momentum from Salesforce's VP of GTM Amelia LeRutte, SaaStr's Chief AI Officer (and the person Jason Lemkin calls "the AI Agent Whisperer"), breaks down exactly how she went from managing a 10-person team to running 20 AI agents that generated $4.8M in additional pipeline — and closed half of it. In this episode, Amelia walks Jonathan Kvarfordt, Momentum from Salesforce's VP of GTM through: — Her journey from social media manager to Chief AI Officer, including the three-month deep dive where she locked herself in a room to figure out AI agents — The full breakdown of SaaStr's 20-agent stack, including how they split work between tools like Salesforce AgentForce, Artisan, Qualified, Clay, Momentum, Gamma, and Zapier — A live demo of their multi-agent workflow: how a single form submission triggers a chain of agents that enrich data, build personalized Gamma decks, and draft follow-up emails, automatically — Real results: deal volume doubled, win rate doubled, and $2.4M closed from AI-sourced pipeline in just 8 months — The "90/10 rule" for deciding when to buy an agent vs. build one with vibe coding on Replit — Live demos of Digital Jason (Delphi), Amelia AI (Qualified), and a sponsor portal being vibe-coded in real time Whether you're running a lean startup or scaling a go-to-market team, this is one of the most tactical breakdowns of an AI agent stack you'll find. 🎟️ Heading to SaaStr Annual in May? Talk to Amelia AI on the event site for a promo code:
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SaaStr 844: The Top 5 Issues Managing Multiple AI Agents in Production with SaaStr's CEO and Chief AI Officer
03/04/2026
SaaStr 844: The Top 5 Issues Managing Multiple AI Agents in Production with SaaStr's CEO and Chief AI Officer
The Top 5 Issues Managing Multiple AI Agents in Production 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. 🔥 THE 5 ISSUES WE COVER: 1. The Context Switching Tax (2:15) Managing 20 agents = managing 20 employees who all speak different languages. Each needs daily 1-on-1s. The math doesn't work: 20 agents × 20 min = 6.7 hours/day, but you only have 3-4 hours of capacity. 2. The New Agent Blackout Period (12:40) 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 (23:15) 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 (32:50) "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 (41:20) 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 (48:30) 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. ⚡ KEY TAKEAWAYS: → There is no orchestration layer yet - you're manually checking 20 different dashboards daily → Your agents can't talk to each other - Salesforce is the only place they meet → You need a "Chief Agent Officer" - someone technical enough to manage the stack → The math: Can only add ~1.5 agents/month max, need 10-15 hours/week for management → ROI calculation is simple: Which agent touched which lead? Did it close? That's it. 💰 THE NUMBERS: → 20+ agents in production → $1M+ in closed revenue from agents → 30% of Chief AI Officer time spent on agent management → 2 weeks minimum to onboard each new agent → 6.7 hours needed daily to properly manage 20 agents (impossible) 🛠️ AGENTS WE USE: 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) 🔗 RESOURCES: → SaaStr.ai/agents - Full agent directory and how we use each one → SaaStr Annual 2026 (May 12-14) - SaaStr Deploy day: Build your own agents hands-on → Previous episodes: Deep dives on 10K AI VPM, vibe coding, build vs buy 🎤 SPEAKERS: 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." #AIAgents #SaaS #GoToMarket #AIAutomation #ProductivityTools #B2BSaaS #SalesAutomation #MarketingAutomation #AgenticAI #StartupTech Subscribe for weekly AI deployment content from the trenches. No theory. No vendor pitches. Just what actually works (and breaks) at scale. --------------------- 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 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 — 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
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SaaStr 843: Software Stocks Have Massively Crashed. Here's What Founders Need to Know.
02/25/2026
SaaStr 843: Software Stocks Have Massively Crashed. Here's What Founders Need to Know.
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. --------------------- 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 --------------------- 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 to get my exclusive discount SaaStr AI SF 2026. We'll see you there.
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SaaStr 842: The 90/10 Rule for AI Agents: What to Build vs Buy with SaaStr's CEO and CAIO
02/18/2026
SaaStr 842: The 90/10 Rule for AI Agents: What to Build vs Buy with SaaStr's CEO and CAIO
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 -------------------------------------- Tools & resources mentioned: Replit, Claude Cowork, Clerk, Lovable, Zapier, Salesforce, Monaco 🔗 See all the AI agents and tools we use: saastr.ai/agents 🔗 SaaStr Annual 2026 (May 12-14): saastrannual.com 🎙️ 20VCwith Harry & Jason & Rory: Drops every Thursday #SaaStr #AI #VibeCoding #B2BSaaS #AIAgents #BuildvsBuy -------------------------------------- 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 --------------------- 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 to get my exclusive discount SaaStr AI SF 2026. We'll see you there.
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SaaStr 841: Going From Blobs to Billions. Clay's Co-Founder Breaks Down Inbound, Outbound, and AI-Powered Sales.
02/11/2026
SaaStr 841: Going From Blobs to Billions. Clay's Co-Founder Breaks Down Inbound, Outbound, and AI-Powered Sales.
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 — 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 --------------------- 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 to get my exclusive discount SaaStr AI SF 2026. We'll see you there.
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SaaStr 840: From 1 Agent to 20+: The Reality of Managing Multiple AI Agents Across Your GTM with SaaStr's CEO and CAIO
02/04/2026
SaaStr 840: From 1 Agent to 20+: The Reality of Managing Multiple AI Agents Across Your GTM with SaaStr's CEO and CAIO
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. --------------------- 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 --------------------- 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 to get my exclusive discount SaaStr AI SF 2026. We'll see you there.
/episode/index/show/saastr/id/39994040
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SaaStr 839: Why Most SaaS Companies Will Fail at AI (And How to Avoid It) with Intercom's CPO
01/28/2026
SaaStr 839: Why Most SaaS Companies Will Fail at AI (And How to Avoid It) with Intercom's CPO
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) --------------------- 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 --------------------- 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 to get my exclusive discount SaaStr AI SF 2026. We'll see you there.
/episode/index/show/saastr/id/39906500
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SaaStr 838: The Present and Future of AI in Sales and GTM with SaaStr's CEO and Owner's CRO
01/21/2026
SaaStr 838: The Present and Future of AI in Sales and GTM with SaaStr's CEO and Owner's CRO
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 --------------------- 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 --------------------- 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 to get my exclusive discount SaaStr AI SF 2026. We'll see you there.
/episode/index/show/saastr/id/39802255
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SaaStr 837: 10 Things To Do Right Now to Become AI Native with Filevine's CEO & Founder
01/14/2026
SaaStr 837: 10 Things To Do Right Now to Become AI Native with Filevine's CEO & Founder
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: 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. --------------------- 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 --------------------- 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 to get my exclusive discount SaaStr AI SF 2026. We'll see you there.
/episode/index/show/saastr/id/39711385
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SaaStr 836: The Step-By-Step Playbook for Building AI-Powered GTM Teams with Personio's CRO
01/07/2026
SaaStr 836: The Step-By-Step Playbook for Building AI-Powered GTM Teams with Personio's CRO
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. --------------------- 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 --------------------- 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 to get my exclusive discount SaaStr AI SF 2026. We'll see you there. --------------------- More from SaaStr: 📺 Subscribe for more AI & SaaS insights #AIinSales #GTM #SaaStr #AIAgents #SalesAI #RevenueOperations
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SaaStr 835: AI + B2B in 2026: Find the Tailwinds or Get Left Behind with SaaStr CEO and Founder Jason Lemkin
01/02/2026
SaaStr 835: AI + B2B in 2026: Find the Tailwinds or Get Left Behind with SaaStr CEO and Founder Jason Lemkin
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 --------------------- 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 --------------------- 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 to get my exclusive discount SaaStr AI SF 2026. We'll see you there.
/episode/index/show/saastr/id/39587900
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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
12/24/2025
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
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 --------------------- 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 to get my exclusive discount SaaStr AI SF 2026. We'll see you there.
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SaaStr 833: AI and the Death of the 2021 Sales Playbook with SaaStr CEO and Founder Jason Lemkin
12/17/2025
SaaStr 833: AI and the Death of the 2021 Sales Playbook with SaaStr CEO and Founder Jason Lemkin
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. --------------------- 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 --------------------- 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 to get my exclusive discount SaaStr AI SF 2026. We'll see you there.
/episode/index/show/saastr/id/39434700
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SaaStr 832: How to Use AI to Hyper-Customize Go-To-Market at Scale with SaaStr's CEO and Chief AI Officer
12/10/2025
SaaStr 832: How to Use AI to Hyper-Customize Go-To-Market at Scale with SaaStr's CEO and Chief AI Officer
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. --------------------- 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 --------------------- 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 to get my exclusive discount SaaStr AI SF 2026. We'll see you there.
/episode/index/show/saastr/id/39354435
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SaaStr 831: How We Use 20+ AI Agents for Marketing & Go-to-Market with SaaStr's Chief AI Officer and CEO & Founder
11/26/2025
SaaStr 831: How We Use 20+ AI Agents for Marketing & Go-to-Market with SaaStr's Chief AI Officer and CEO & Founder
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 . --------------------- 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 --------------------- 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 to get my exclusive discount SaaStr AI SF 2026. We'll see you there.
/episode/index/show/saastr/id/39179310
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SaaStr 830: 6 Months Later, How Our AI SDRs Actually Work as AI Runs GTM with SaaStr's CEO and Chief AI Officer
11/21/2025
SaaStr 830: 6 Months Later, How Our AI SDRs Actually Work as AI Runs GTM with SaaStr's CEO and Chief AI Officer
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 . --------------------- 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
/episode/index/show/saastr/id/39125005
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SaaStr 829: A Hands-On Guide to SaaStr's New AI Tools with SaaStr CEO and Founder Jason Lemkin
11/12/2025
SaaStr 829: A Hands-On Guide to SaaStr's New AI Tools with SaaStr CEO and Founder Jason Lemkin
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 . --------------------- 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 --------------------- 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 to get my exclusive discount SaaStr AI SF 2026. We'll see you there.
/episode/index/show/saastr/id/39005010