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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SaaStr 864: How to Build Your Own AI VP of Marketing Step-by-Step with SaaStr's Chief AI Officer
How to Build Your Own AI VP of Marketing Step-by-Step with SaaStr's Chief AI Officer SaaStr's CAIO Amelia LeRutte built 10K, SaaStr's AI VP of Marketing, live on stage at SaaStr AI Annual 2026 - and you can follow along and build your own right now. 10K started as a simple dashboard in January. Five months later it runs autonomous email campaigns, generates daily marketing ideas grounded in real data, sends attendee newsletters, and acts as a full co-pilot for SaaStr's entire go-to-market. In this session, Amelia walks you through the exact spec, the sample data, and the live build so you can deploy your own version before the video ends. What you'll learn: How to write a spec that gives your agent one clear goal and actually produces useful outputs How to connect Salesforce, your marketing automation platform, social media, and other APIs so your agent has real data to work with The stair-stepping approach: build one agentic workflow at a time instead of trying to automate everything at once How to set guardrails so your agent runs campaigns semi-autonomously without emailing your entire database by accident What 10K does today versus what it could do on day one, and what the realistic 30, 60, and 90-day build looks like Resources from this session: Grab the spec and sample historical data to build your own: saastrannual.com/resources Free Replit credits: use code REPLITSAASTR Read 10K's own take on whether he is a VP of Marketing: saastr.com/is10kavpofmarketing About this session: Recorded live at SaaStr AI Annual 2026 in San Mateo. Part of SaaStr's ongoing series on building and deploying AI agents
SaaStr 863: The Enterprise AI Reality Check: From Dashboard Graveyards to 30-Day Migrations with Databricks' Co-Founder and SVP of Field Engineering
SaaStr 863: The Enterprise AI Reality Check: From Dashboard Graveyards to 30-Day Migrations with Databricks' Co-Founder and SVP of Field Engineering Every Fortune 500 CEO has told their team that if they are not using AI, they are behind. So now every employee is token-maxing, spend is going up, and almost nobody can tell you what they are getting out of it. That is the reality Databricks sees from the front lines, serving more of the Fortune 500 than any other data and AI company on the planet. In this episode, Databricks Co-Founder and SVP of Field Engineering, Arsalan Tavakoli, sits down with SaaStr CEO and Founder, Jason Lemkin, to cut through the Twitter noise and talk about what enterprises are actually doing, what is still broken, and why the next 24 months will fundamentally change who wins and who loses in every major software category. You'll learn: Why the BI dashboard is dead and what replaces it - including how a car manufacturer just onboarded 70,000 non-technical users to query their own data in plain language with no analyst in the loop What "context" actually means for enterprise AI and why it is harder to solve than the data problem, using a framework that explains why agents fail even when the underlying data is clean Why no software monopoly survives the next 24 months, and how collapsing migration costs and low-end AI competitors are about to give every incumbent a pricing problem they cannot ignore How Databricks now completes enterprise-grade migrations in 30 days or less using LLMs to analyze, convert, and reconcile legacy systems that previously took years and cost more than the savings Why the murky middle is the most dangerous place to be in enterprise software right now, and how to know which side of the AI budget divide your product actually sits on
SaaStr 862: The Dashboard Is Dead: What Snowflake's CMO Does Instead
The Dashboard Is Dead: What Snowflake's CMO Does Instead Denise Persson runs a 700-person marketing organization at one of the most data-rich companies on the planet, and she does not start her morning by logging into a dashboard. She interrogates her data directly, gets answers to questions she used to have to Slack three people about, and moves on. No meetings about the numbers. No debates about what the pipeline data means. No waiting until end of quarter to find out if a campaign worked. In this session, Denise joins SaaStr CAIO Amelia LeRutte to break down what AI-powered marketing actually looks like when you have the scale, the data infrastructure, and the compliance requirements of Snowflake, and what founders and marketing leaders at any stage can steal from the playbook right now. You'll learn: How Snowflake cut cost per opportunity by 30% by using agents to optimize media spend in real time across fragmented channels that used to require separate analytics for each What Denise's morning brief actually contains, from pipeline projections to org health to flagged travel expenses, and why nobody gets a Slack message from her anymore Why the GTM engineer is the only marketing function Snowflake is actively hiring into, what profiles are converting into the role, and why business analysts are not making the list How to build AI fluency across a large team without making it mandatory or performative, including the weekly AI challenge, quarterly AI days, and a leaderboard that rewards curiosity over token count Why data quality is the single most important investment before deploying any agent, and why bad data plus AI just means bad decisions faster and at scale This is for you if: You lead a marketing team of any size and want to see what the "most AI-assisted marketing team in B2B" actually looks like in practice, not in a slide deck You are trying to figure out how to get a large or compliance-sensitive org moving on agents without losing control of what they are doing You want to understand what the GTM engineer role actually looks like day to day and how to find or develop one inside your existing team
SaaStr 861: Our AI Agent Negotiated a Vendor Renewal, Became a CFO and a Better SDR .. But Does He Have Too Many Guardrails?
The Agents #007: Our AI Agent Negotiated a Vendor Renewal, Became a CFO and a Better SDR .. But Does He Have Too Many Guardrails? Episode 7 of The Agents, SaaStr's weekly show on the trials and tribulations of running a company with 21 AI agents, 3 humans, and a dog. This week Jason and Amelia debrief life after SaaStr AI Annual and discover that the agents didn't slow down just because the event ended. 10K is already planning SaaStr 2027, negotiating vendor renewals on his own terms, and somehow became a CFO while nobody was looking. Meanwhile, a guardrail problem quietly broke one of SaaStr's most-used apps for weeks, and the website agent is now outperforming every AISDR in the stack. This week: 14 guardrails pushed the VC pitch deck analyzer into rejecting everything, and the lesson is that over-guardrailing is just as dangerous as under-guardrailing. 10K got hooked up to Bill.com and found 8 years of collections automation that nobody had turned on. The AI VP of Marketing is now also running finance because convergence is real and agents do not care about org charts. And 10K sent a vendor a list of API demands before agreeing to renew, which the vendor did not love. Also: why losing your FDE might make you churn the vendor entirely, why Annie the website agent is writing better outbound than the actual outbound tools, and how 442,000 chats turned into 614 meetings with zero humans in the loop.
SaaStr 860: Tired vs. Wired: $4 Trillion in IPOs Coming, $100B in M&A, and Why the SaaSpocalypse is Over
Tired vs. Wired: $4 Trillion in IPOs Coming, $100B in M&A, and Why the SaaSpocalypse is Over The public markets spent the last twelve months telling you B2B software was finished. Stocks down 60 to 70 percent. PE firms buying nobody. For the first time in history, software trading at a discount to the S&P 500. And at the exact same moment, Anthropic is projecting $50 billion in revenue, Cursor is getting acquired for $60 billion, and SpaceX, Anthropic, OpenAI, and Databricks are about to generate more market value than every other IPO since 2000 combined. Both things are true - and which one defines your next 18 months depends entirely on one question: are you tired or are you wired? In this episode, SaaStr CEO and Founder Jason Lemkin calls the market as he sees it, names who is winning and who is pretending, and makes the case that the Cambrian explosion in B2B is just getting started. You'll learn: Why the SaaSpocalypse was never about B2B dying - it was about pre-AI software dying - and what the Palantir, Twilio, and Atlassian re-acceleration stories actually tell you The four categories every B2B company falls into right now, and why category four founders need to stop pretending the recovery is coming on its own Why vibe coding your CRM is dead as a concept, and what "putting deals on your calendar" actually means as a product strategy Why your biggest near-term competitive edge might be two days of engineering work - making your API agent-friendly before your competitors do What SaaStr's own journey from 20 humans to 3 humans and 21 agents teaches you about consistency as the only real cheat code in agents This is for you if: Your growth has slowed and you are not sure whether it is a market problem or a you problem - this session will help you figure out which You are a founder or exec who has been in the "AI is coming" conversation for a year but has not yet seen it show up in your revenue You want the unfiltered version of where B2B is headed in the next 18 months, including the parts most people are too polite to say out loud
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