Dear SaaStr: We Lost an Enormous RFP Because We are Too Small. Any Advice?
Dear SaaStr: We lost an enormous RFP because we are too small. Any advice? This is indeed a big bummer. But it truly does make you stronger. If you commit to winning the next one. Six thoughts on how to do better next time: First, move them into your Lost Now (But...
We Have 20+ AI Agents and Just 3 Humans. But Even So, We Still Need “Real” B2B Software.
We hear this a lot: “Once you have AI agents the work, you don’t need CRM. Just give them a Postgres database and let them rip.” It sounds clean. It’s also wrong, I think. At least for 99% of us. At least for now. At SaaStr AI, we’ve gone...
The 20 Minute Test in VP Hiring. Maybe All Hiring
Investments rarely work out if you don't believe within the first 20 minutes I think I'm there on hiring, too now If you don't believe at least by minute 20 of the first Zoom that they're the VP for you … I'd pass — Jason ✨👾SaaStr.Ai✨...
Dear SaaStr: Is it OK to Modify the Standard SAFE Form?
Dear SaaStr: Is it OK to Modify the Standard SAFE Form? Ideally don’t. If you do — at least be transparent and crystal clear on what changes you are making. SAFEs require a high degree of trust to work. Hiding changes undermines that trust....
5.4M Impressions Driving 11,749 to Their Signup Form: What Advertising on SaaStr.AI Media Actually Delivers
Most B2B media buys are … a black box. You sign up, wire the money, the ad “runs,” and 60 days later you get a PDF with an impressions number and no way to check any of it. You have no idea if a single real buyer even saw it. We do it differently at...
The Sub-5% Club: The Terminal State of Software
For twenty years, the slow lane in B2B wasn’t great. But it was an OK place to be. Growth faded, but the annuity was forever. High NRR, high margins, sticky contracts, structured data that was stuck in an app and couldn’t leave, predictable cash. You...
If Your VP Sales Isn’t Going to Work Out — You’ll Know in 30 Days
New SaaStr Fund portfolio company CRO his first week on the job: Note: he also started before he started. We’ve talked a lot on SaaStr about how to make that critical hire: the VP Sales. I’ve done it right, and I’ve done it wrong. When it’s...
Jason’s Takes on This Week’s 20VC: The Token Governor, the Net-New-Logo Test, and Why Renewal Stopped Being Safe
Going a level deeper on the points Harry, Rory and I hit this week, and what they actually mean if you’re building a B2B company right now. Here were the top SaaStr learnings I wanted to share from this weeks’ deep dive with the 3 of us. 1. If You Can Hire...
What a Great VP Sales Does In Their First Week. Watch For It.
One of the most controversial things I’ve said over the years on SaaStr is: You know within 30 days if you hired a VP right. Especially a VP of Sales. Not at 90 days. Not at 6 months. By day 30, the split is visible. And if you’re not paying attention,...
Sales Rep Annual Quotas in 2026: What High Performers Are Actually Carrying: $750k for SMB, $1.35m for Mid-Market, $2.25m for Enterprise
ICONIQ recently released their 2026 GTM benchmark report, and it shows that overall sales quotas and processes are similar to the pre-AI era. Just … ramped up. Top-quartile enterprise AEs are now carrying $2.25M annual quotas Mid-Market is $1.35M SMB is $750K...
SaaStr AI App of the Week: Nue. The Revenue Platform Built for How B2B + AI Actually Prices Now
The hardest problem in B2B + AI right now is not building the product. It’s pricing it. Every AI company is walking away from pure per-seat and toward usage, consumption, credits, and outcome-based models. The tooling most of them run to quote, bill, and...
Claude Became Our AI VP of Product. We Moved 10 Years Off Marketo for $14. Our Agent Killed a $10K App in an Hour: The Agents #010
Amelia and I just published Episode #010 of The Agents. Same setup as always: three humans, 21+ agents in production, an 8-figure B2B + AI business and $200m of investments at SaaStr AI Fund, revenue running 140% of last year and growing again. Every week we get into...
5 Interesting Learnings from Zoom at ~$5 Billion in ARR: Modestly Re-Accelerating Growth, Real AI Monetization, a $27B Market Cap, and a 25x Anthropic Windfall
Almost everyone wrote Zoom off a few years back. The innovative app everyone loved before 2020, but then almost a COVID one-hit-wonder that peaked in 2021 after going from $1B to $4B in ARR in one year. That would slowly bleed out as people went back to the office...
Dear SaaStr: Do Any Top B2B Events Give You “The List”?
Dear SaaStr: Do Any Top B2B Events Give You “The List”? No, no good ones do, and for good reason. Top tier B2B events, especially ones focused on quality over volume, deliberately don’t hand over attendee lists to sponsors as a blanket data asset. If...
Founder SaaStr
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