The #1 Error with AI GTM Agents: Assuming They Can Do What Your Team Hasn’t Already Figured Out
We’ve been going deep on AI agents across SaaStr for the past 12+ months. We’ve deployed 20+ AI agents that now generate over $1M in revenue. We’ve watched hundreds of B2B companies try to implement AI SDRs, AI customer success agents, AI sales...
“The Dumbest Idea I’ve Ever Heard” — How Own Became a $2B Salesforce Acquisition
A SaaStr AI deep dive with Sam Gutmann, CEO of Own, on building a billion-dollar backup company by saying “no” to almost everything. He joined Harpinder Singh (Partner, Innovation Endeavors) to share the whole story — and his top mistakes. And come...
Dear SaaStr: Which Tactics Always Work to Drive Down Churn, and Drive Up Retention?
Dear SaaStr: Which Tactics Always Work to Drive Down Churn, and Drive Up Retention? The best tactic I’ve ever seen is a simple combination of 3 things: Measure it, Segment it, and Drive it Down — Irrespective of Where It is Today. Churn is a bummer, and high churn is...
The 2026 SaaS Crash: It’s Not What You Think
Software stocks just entered a bear market. IGV is down 22% from its highs. January 29 was the worst single day for software since the Covid crash. ServiceNow dropped 11% despite beating earnings for the ninth straight quarter. Microsoft shed $360 billion in market...
“Digital Jason” Has Answered 73,915 Questions. And It’s Free. Try It!
I used to get 500+ emails a day asking questions I’d already answered somewhere in 4,600 blog posts, 13 years of podcasts, and hundreds of hours of video. The problem was never the answers. The answers existed. The problem was finding them, in your context, at...
I Wrote Off $4M to $0. My Co-Investor Marked Up the Same Deal to $30M. Here’s What Founders Need to Know About VC Incentives.
So at the end of last year, I made my biggest write-off ever at SaaStr Fund. $4 million to $0. Gone. But here’s what’s wild: my co-investor in the exact same deal? He marked up his investment. From about $15 million to $30 million. Same company. Same...
Dear SaaStr: How Long of a Ramp Period Should I Give a New VP of Sales?
Dear SaaStr: How Long of a Ramp Period Should I Give a New VP of Sales? Look, to be clear, the best ones just hit the ground running. Their first week and really even their first day. Everyone else … looks a little lost when they start 😉 For a Head of Sales at...
The #1 Conceit in B2B at Scale: Masking a Slowdown in Net New Customers
Why Covering Up Declining Customer Growth is the Beginning of the End I’ve seen this movie play out dozens of times now across hundreds of B2B companies. And it almost always ends the same way. The #1 conceit in B2B — the thing that kills more companies than bad...
The Trade Desk Was Priced for Perfection. Then Growth Slowed. Now It’s the Worst Performing Stock in the S&P 500.
The Trade Desk was the darling of adtech. A profitable, founder-led adtech software company that grew at epic rates year after year, built the leading independent demand-side platform, and positioned itself as the Switzerland of programmatic advertising. And then it...
Dear SaaStr: What Are Some of the Qualities of a “Bad” Startup CEO?
Dear SaaStr: What are some qualities of a bad startup CEO/founder in Silicon Valley? A few that I’ve seen across the handful of investments I’ve made … that didn’t work out: Not really committed to going long. This doesn’t so much make you a “bad” CEO as one that...
The Best AI Startups Do the Training For You. It’s On You to Make the Agent Awesome — Not Your Customers.
Think about how customers bought enterprise software in 2019. Or even in 2023. You’d get sold by a sales rep. Then you’d hire an Accenture or other third party to deploy it over 9-12 months. And you’d hope and pray it worked like the sales rep...
Want Leads? Sponsor the Next SaaStr AI Day. And Then SaaStr AI Annual 2026 in May!
Here’s the deal: our quarterly SaaStr AI Days are generating 370-634 leads per sponsor right now. The next one is coming up at the end of March! That’s not badge scans from people wandering by. That’s registered attendees specifically interested in...
Dear SaaStr: What Are The Signs We’re Ready to Hire More Sales People to Scale?
Dear SaaStr: What are the signs that an enterprise SaaS startup is ready to scale by hiring more sales people? In the early days, it’s simply that you have a few more leads than you can currently handle. For a higher-velocity, in-bound driven B2B product, most sales...
20VC x SaaStr This Week: The $5 Billion Exit That Felt Weird, Why Inference Costs Are the Final Nail for Mid Growth SaaS, and Andreessen’s 2/3 AI Domination
The latest from the 20VC x SaaStr collaboration with Harry Stebbings, Jason Lemkin, and Rory O’Driscoll The TL;DR Brex sold for $5.15 billion—a heroic outcome by any rational standard, yet the weird feeling in everyone’s stomach tells you everything about...
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