Dear SaaStr: How Should I Specialize My Sales Team?
Dear SaaStr: How Should I Specialize My Sales Team? If you’re asking the question, then the answer is probably yes 😉 One thing is clear: most founders and VPs of Sales and CROs look back and wish they’d specialized their sales team earlier. And not have...
The Top 12 Sales Lessons From SaaStr AI 2026: Anthropic, Gamma, Owner, Stripe, Salesforce, Vercel, Replit and Monaco
The sales and GTM sessions at SaaStr AI 2026 in San Mateo was all about where to take agents next. No one was still debating whether to put agents in the revenue org. They had already done it, and they brought the war stories. What broke, and what they would do...
Dear SaaStr: We Have a Sales-Led Motion and SMB Customers And The Economics Aren’t Working
Dear SaaStr: We Have a Sales-Led Motion and SMB Customers And The Economics Aren’t Working. What Do You Suggest? You have to be ruthlessly efficient with a sales-led SMB motion. It can be done: Toast does it at a $10k ACV with fairly low gross margins: Slice...
Our New AI VP of Finance Closes the Deal, Sends the Invoice, and Chases the Cash. It Took 4 Deals to Train It.
Our finance team went on vacation during SaaStr AI Annual. Our busiest time of the year. That’s the whole origin story. Collections started slipping, sponsors and vendors weren’t getting billed, and the work that has to happen after a deal closes stopped...
Dear SaaStr: How Do I Learn to Close Big Enterprise Deals … Better?
Dear SaaStr: How Do I Learn to Close Big Enterprise Deals Better? Closing high-ticket enterprise deals is a different beast compared to SMB or mid-market sales. It requires patience, strategy, and a deep understanding of the enterprise buying process. In fact,...
Build on the Stack You Have: How Anthropic’s Head of Industries, Atlassian’s Head of AI, and Scale’s Rory O’Driscoll Landed on the Same AI Playbook
Three of the strongest sessions at SaaStr AI 2026 came from three very different seats. Sharif Mansour runs AI and the product management craft across Atlassian’s 20+ apps and 450 product managers. Eleanor Dorfman leads the commercial and industries sales team...
Dear SaaStr: When Should We Start Pushing For Multi-Year Contracts?
Dear SaaStr: When Should We Start Pushing For Multi-Year Contracts? For most of us: stop pushing for them in the Age of AI. The market has shifted, and fighting it costs you more than it gains. Here’s the reality: shorter contracts are now the norm across B2B +...
We Peaked at 30 AI Agents. Now We’re Coming Back Down to 20. Here’s What Consolidation Actually Looks Like. The Agents #011 Live!
We run SaaStr with 3 humans and 21+ AI agents. This is a real eight-figure B2B business with real customers, real invoices, and a real collections problem, and the agents run it. About a month ago we hit a wall. Amelia and I realized we could not manage one more...
You Should Be Collecting At Least 100% Of Your MRR Each Month in Cash. Ideally, 110%+.
"Make sure every month you collect at least 100% of your MRR. Ideally, 110%. If it falls below 100%, you have a process failure in finance. And your runway may be far shorter than you expect." pic.twitter.com/6TlJaMdXdk — Jason ✨👾SaaStr.Ai✨ Lemkin...
5 Interesting Learnings from Stripe at $6.8 Billion in Revenue: 33% Growth, 47% Free Cash Flow Margins, and a $53B Bid for PayPal
Stripe is still private, so we mostly get data when the company chooses to give it to us. This week we got more than usual. The Information reported Stripe’s 2025 revenue hit $6.8 billion, up roughly a third year-over-year, its fastest growth since 2021. Free...
AI Won’t Kill SaaS. But It Will Kill Vendors That Stopped Shipping. Point Solutions Are Most at Risk.
Let me start with where I actually land on build-vs-buy: I’d rather not build or vibe. Almost ever. If you can buy it — buy it. The 90/10 rule. ~90% of the time, you should buy. Even more, really. If you can find it, and it meets 90% of your needs, buy...
How a Mediocre Sales Team Loses You Deals. Ones You Could Have Won
A vendor reached out to me last week for fund administration for SaaStr Fund. We are genuinely in the market for a vendor and it’s a $100k+ a year potential client. This should have been a real shot for them. It started on LinkedIn, where they reached out. I...
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...
Founder SaaStr
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