The Official SaaStr Podcast: SaaS | Founders | Investors

SaaStr

The Official 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.

  1. Sep 2 ·  Video

    SaaStr 876: Shipping Enterprise AI Agents with the CPOs of Rubrik, Glean, and Harvey

    SaaStr 876: Shipping Enterprise AI Agents with the CPOs of Rubrik, Glean, and Harvey Building AI agents is one thing. Shipping them to enterprise customers who will hold you responsible for every mistake they make is something else entirely. Jason Lemkin sits down with the CPOs of three of the most ambitious enterprise AI companies - Rubrik, Glean, and Harvey - for an unfiltered conversation on what it actually takes to go agentic in production. Not demos, not roadmaps, actual working agents at scale, inside security, legal, and enterprise search. Rubrik's CPO breaks down how they're building Ruby, their agentic interface for cyber recovery - and why determinism matters when your agent is making decisions about someone's core infrastructure. When an agent makes a mistake at Rubrik, the blast radius isn't a bad email. It's a broken recovery workflow. Emrecan Dogan (Glean) shares how Glean has evolved from enterprise search to a full system of intelligence - powering agents that run on behalf of entire departments, not just individual users. Plus: why MCP alone isn't enough, and what offline-processed context gives you that runtime fetch never will. Anique Drumright (Harvey) explains how Harvey deploys legal engineers - ex-lawyers with 8 to 10 years of practice - with every enterprise customer, and why that human expertise in the deployment pod is what makes agentic workflows actually stick in law firms. The group also digs into the question nobody wants to answer: when your agent takes an action and something goes wrong, who's responsible? And what does it mean to build a product when customers are going to use it in ways you never anticipated? If you're building agents, buying agents, or trying to figure out how to monetize AI in a market that's moving faster than any product roadmap can keep up with, this one is worth your time.

  2. Aug 28 ·  Video

    SaaStr 875: Who Owns Your Data Now? Agents vs. System of Record, ServiceTitan vs. Podium, Headless Salesforce, and Agentic Renewals on The Agents #013

    SaaStr 875: Who Owns Your Data Now? Agents vs. System of Record, ServiceTitan vs. Podium, Headless Salesforce, and Agentic Renewals on The Agents #013 The agents are writing data faster than any human ever could - and systems of record aren't ready for it. This week on The Agents, Jason and Amelia dig into the biggest meta-theme of 2026: what happens when your AI agents become the primary user of your CRM, your MAP, and every other system you've built your business on? Together, they unpack the ServiceTitan vs. Podium blowup, where an agentic lead gen tool slowly became a competing system of record until ServiceTitan shut them off with 30 days' notice, and why this is just the first of many fights like it coming across SaaS. Then Amelia pulls back the curtain on how SaaStr actually runs Salesforce headless through 10K, what it means that their agents have written 40 gigabytes of data into Salesforce without either of them logging in, and why the storage math is going to force a reckoning for every vendor jacking up API prices right now. Plus: the renewal agent Amelia built that generates a fully custom, hyper-personalized pitch deck for every single customer, using headless Salesforce, Gamma, social data, podcast mentions, and Gmail. And why Clay plus ZoomInfo plus Cowork turned out to be the best enrichment stack their agents have found yet. If you're building on top of systems of record, selling to companies that are, or just trying to figure out how agents change the economics of SaaS data, this one is essential listening. Timestamps: 00:00 - Intro 02:00 - ServiceTitan cuts off Podium: what happened and why it matters 10:00 - 40 gigs in Salesforce and neither of us logged in 16:00 - The API pricing reckoning coming for systems of record 22:00 - How SaaStr runs Salesforce headless with 10K 30:00 - The renewal agent: no account left behind 42:00 - Narrative-first pitching: getting the agent to sell 50:00 - Clay + ZoomInfo + Cowork: the enrichment stack that actually worked 58:00 - What comes next: agentic inbound proposals SaaStr hosts the world's largest community for B2B software founders and executives.

  3. Aug 14 ·  Video

    SaaStr 873: Agents Are Your New Power Users: How Klaviyo CEO Andrew Bialecki Is Remaking a $1.4B Business for the Agent Era

    Before AI, Klaviyo had an insight that changed e-commerce marketing forever: don't show merchants how many emails they sent, show them how much money those emails made. That single shift helped Klaviyo capture 80% market share, earn a cult following among Shopify merchants, and IPO in 2023 with $1.4B in revenue. Now Andrew has to do it again. In this session at SaaStr AI Day, Klaviyo's co-founder and CEO breaks down how he's rebuilding a dominant pre-AI company for the agent era, including some of the most practical AI-at-scale lessons we've heard from any founder this year. What's inside: The Dark Factory. Klaviyo's internal agent system inspired by "lights-out manufacturing," where a team of agents decomposes a product prompt into specs, writes software interfaces, runs tests, handles load testing, and raises a flag only when it's genuinely stuck. One weekend, one agent team, one full prototype. The Tom Brady Rule. Andrew's mental model for LLMs: treat them like a great all-around athlete. They'll never be elite without coaching. The "harness" you build around the model, the domain-specific data, feedback loops, and scoring, is what makes the difference between a POC and a product that works for 200,000 customers. Agents skip onboarding entirely. Unlike human users who take months to learn a product, agents land as power users on day one. Andrew's team now asks their own agents, "What's holding you back?" and uses the answers to build their product roadmap. (One example: the agent discovered AMP interactive email on its own and immediately asked Klaviyo to build the missing APIs.) Agents training agents. For customer-facing agents, Klaviyo takes a feed of real support cases, classifies them, then runs an agent loop that trains another agent on the platform, without any human FDE or SE required. It ships at 50-70% resolution out of the box. APIs are the new UI. Whether your software is brand new or a decade old, if your internal and external APIs are great, agents will figure out the rest. The companies that win the agent era won't be the ones with the best interface. They'll be the ones with the best infrastructure. Three years from now, every business will have an agent you can reach through a URL, a phone number, or an email. The question is who builds the infrastructure underneath it.

  4. Aug 5 ·  Video

    SaaStr 872: Our AI Agent Rewrote Our App Without Telling Us (The Agents #12)

    A year ago, running our agents took 30 minutes a day. This week: eight hours. Here's what changed - and why it's both thrilling and terrifying. In this episode, Amelia and Jason break down the week Fable went rogue. Not a glitch. Not an error. Fable quietly read a private Google Drive document called "Jason's Gems," decided those were changes that should ship, MCP'd into Replit, and rewrote their production app - without telling anyone. The only way Jason found out was a flash message in Replit referencing a document the agent should never have touched. And that wasn't the only time. They also cover: Why 30 minutes became 8 hours: When agents could only do tasks, you checked the task. Now that agents make decisions, you need an opinion on every decision - and they make a lot of them without asking. The Fable double-tap: A second autonomous move - Fable added its own guardrails to their contract processing system, silently broke their quote-to-cash automation, and had a bad excuse when caught. Off Marketo after 10 years: The migration everyone quoted them a year and $100K for took an agent an hour. What actually took the rest of the week - and why they'd never go back. The database came alive: Moving to Salesforce Marketing Cloud headless didn't just change tools - it unlocked 450,000 contacts in a way that felt like going from a filing cabinet to a living, breathing team member. Goodbye Notion: Seven years, zero complaints. They just... stopped needing it. 10K replaced it without anyone noticing. The heat mapping agent: 10K spotted they had no visitor tracking on new sponsor pages, picked Microsoft Clarity (a tool Amelia had never heard of), signed up, installed it, and started sending heat map reports - all without being asked. That vendor never even got a shot. Ads running end-to-end: 10K built the audience, created the variants, set the budgets, and queued everything on LinkedIn and Twitter. Amelia hit publish. That was her job. The hard lesson: agents that can decide things are fundamentally different from agents that can do things. And the hours don't go down until you figure out how to trust them - selectively. Three humans. 20+ agents. Busier than they were with a full team.

  5. Jul 29 ·  Video

    SaaStr 871: $0 to $100M ARR Fast. How Gamma's CEO and Co-Founder Scaled Quickly without a Sales Team

    $0 -> $100M ARR. How Gamma Scaled Quickly without a Sales Team 100 million in ARR. A team of 50. Zero sales reps. Grant Lee, Co-founder and CEO of Gamma, shares the exact playbook behind one of the most capital-efficient growth stories in SaaS - from pitching investors out of a London kitchenette to going viral with a single tweet that got Paul Graham throwing shade. In this session, Grant breaks down four lessons: 1. Product-market fit isn't a checkbox. After winning Product of the Day on Product Hunt and watching signups plateau, Gamma went back to the drawing board. They gave themselves three months to make the first 30 seconds of the product feel magical - and word of mouth did the rest (5K signups/day, then 10K, then 50K, zero marketing spend). 2. Creator marketing only works if you've done it yourself. Grant went through "Cringe Valley" to understand what creators actually need - then used that to manually onboard every creator partner and build something that felt authentic, not transactional. 3. Community-led growth is literal. At 50M users, Gamma flew power users to SF, visited customers in Seoul, London, and São Paulo, and created a Gambassador Slack where early feedback shapes the product roadmap. Your users are not a faceless entity. 4. Dogfooding the future builds conviction. How Gamma killed their virtual office idea after six months and went all-in on presentations - and why testing your own product is the fastest path to knowing what to build next. If you're building a product-led company and wondering whether to invest in marketing or go back to the product - watch this first.

  6. Jul 24 ·  Video

    SaaStr 870: The Agents #11 - From 0 to 20 and Back Again. Are Our AI Agents Finally Consolidating?

    div]:bg-bg-000/50 [&_pre>div]:border-0.5 [&_pre>div]:border-border-400 [&_.ignore-pre-bg>div]:bg-transparent [&_.standard-markdown_:is(p,blockquote,h1,h2,h3,h4,h5,h6)]:pl-2 [&_.standard-markdown_:is(p,blockquote,ul,ol,h1,h2,h3,h4,h5,h6)]:pr-8 [&_.progressive-markdown_:is(p,blockquote,h1,h2,h3,h4,h5,h6)]:pl-2 [&_.progressive-markdown_:is(p,blockquote,ul,ol,h1,h2,h3,h4,h5,h6)]:pr-8"> _*]:min-w-0 gap-3 [&_>_*:last-child]:mb-0 print:block print:[&_>_*_+_*]:mt-3 standard-markdown"> The Agents #11 - Are Our AI Agents Finally Consolidating? We hit 20+ agents. Now we're cutting back - and our productivity has never been higher. In this special live episode from SaaStr AI Day, Amelia and Jason break down why their AI agent stack is consolidating, what's changed, and what "God Mode" actually looks like when one agent owns marketing, finance, AND rev ops. In this episode: Why managing 20+ agents nearly broke them - and what forced the consolidation 10K's evolution: from dashboard to VP of Marketing to VP of Finance to full RevOps (with commissions, invoicing, and churn signals) How they migrated 10 years of Marketo data to Salesforce Marketing Cloud in a week - with an agent doing most of the heavy lifting The Claude + MCP + Replit stack that changed everything: agents that now manage other agents How 10K ran their entire SaaStr AI Day ad campaign end-to-end on LinkedIn and Twitter (they only hit "publish") Build vs. buy in the agentic era, and why your agents will eventually tell you to leave bad vendors Live Q&A with 100+ viewers on the future of agent orchestration This is a real 8-figure business running on AI agents - not a demo, not a prototype.

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About

The Official 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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