Dear SaaStr: What Should I Do if My Co-founder is a Complete Jerk? It if’s that bad — it’s just not going to work. The issue isn’t so much that he’s a complete jerk. Maybe he is, maybe he isn’t, or most likely, it’s somewhere in the middle. It’s that you think he is. He’s…
Continue Reading

Dear SaaStr: Have You, As a CEO, Ever Stood Up for Your Employee Against a Customer? Yes — and to be honest, I do regret it. Yeah ago, the largest software company in the world agreed to be our largest customer. It was a huge victory. But then our top sales rep the next day…
Continue Reading

Dear SaaStr: How do I Convince My CEO that Marketing is Important? A lot of CEOs these days do seem to be late to truly invest in B2B marketing, and most especially, to hiring a true VP of Marketing. In the Age of AI, so many CEOs hack it to $5m, $8m, $20m+ in ARR…
Continue Reading

Probably yes. And the sooner you accept that, the sooner you can build a sales motion that actually works in 2026. Here is what the data shows: average initial contract lengths have been declining across B2B for the past two years. According to ICONIQ’s January 2026 survey of 150+ GTM executives, the shift is consistent…
Continue Reading

If growth has been declining linearly for two years, you’re in a tough spot. Not a hopeless one. But a tough one that requires honest assessment and decisive moves — not incremental tweaks. But first, let’s be clear about what’s happening in the market right now. Because the context matters enormously. The Market Has Completely…
Continue Reading

Short answer: Only in very specific cases, and it usually means you need to hire a different type of person. Most CSMs aren’t built for FDE work. That’s not a knock on them — they’re doing a completely different job. A CSM manages relationships, mitigates renewal risk, and drives expansion across a portfolio of 8–12…
Continue Reading

Longer than the vendor told you. But shorter than hiring another rep. Here’s the real answer: the technology is live in days. The training that makes it actually work takes 60 days of focused effort. Most companies skip the training. That’s why most AI SDR deployments fail. Let me break down what the work actually…
Continue Reading

Dear SaaStr: Should I Use an AI SDR Before I Have a Working Human SDR motion? No. This is the single biggest mistake I see across all company stages, from $1M ARR startups to multi-billion-dollar public companies, and it will sink your AI SDR deployment. The Core Problem If outbound doesn’t work with humans, buying…
Continue Reading

Dear SaaStr: We’re at $8m ARR growing 90% but aren’t really AI Native. VCs won’t take a meeting. Is fundraising hopeless right now? Not hopeless. But brutally honest? You’re in the hardest fundraising environment we’ve ever seen, and here’s why. The Reality: At $8M ARR growing 90%, you’re objectively doing great. You’re in the top…
Continue Reading

Dear SaaStr: Our CFO sounds very polished but we are missing the burn rate plan almost every month, and he takes no responsibility for it. What should i do, if anything? This is a serious problem, and I’d be direct: you need to act on this now. Here’s what I’ve seen happen a hundred times: A…
Continue Reading

Dear SaaStr: Should I Hire More FDEs or CSMs for Our AI Agent Product? That depends entirely on where your bottleneck actually is right now. In AI B2B, deployment is the new constraint — not retention. If customers are signing but not going live, or they’re live but underperforming, you need FDEs. If customers are…
Continue Reading

Dear SaaStr: At What Stage Should a Startup Hire a CMO? Answer: Roughly, when demand gen is no longer the core function of marketing. This also often is the time when you are ready to expand beyond a core small, effective, efficient marketing team: When you have enough of a lead generation engine going, AND…
Continue Reading

Dear SaaStr: Is it Bad to Leave a Stuggling Startup? It can be a tough situation. And one more and more folks are in today. It’s toughest when you are in a critical role. Especially one with no redundancy, and no one else to take your place. If you’re a critical resource and leave a…
Continue Reading

Dear SaaStr: How Should I Present The Competition Slide of My Pitch Deck if I Have Too Many Competitors? Simple Answer: Just pick the Top 5 competitors, that’s enough. Not just by revenue, but also, by significance. Longer Answer: The competitor slide is a chance to: Position your company vs. the rest Help VCs get…
Continue Reading

Dear SaaStr: Should Your Ask a Prospect What Competitors They Are Looking At? Yes. You’ll find 90% of the time you’ll want to not just tell a client who you are competing with — but do so aggressively. And box the competition out at the start. “Great to learn about your business! Is there anyone…
Continue Reading

Dear SaaStr: What are the different strategies to retain an angry customer? Let’s start with one important learning: angry customers usually aren’t lost customers. If they’ve already decided to leave you for another vendor, they generally just go dark instead. So you still have a shot not just to save them and keep them, but…
Continue Reading

Dear SaaStr: I keep hearing about “vibe coding” and founders building their own internal tools with AI. But we already pay for a bunch of B2B products. When does it make sense to vibe code something yourself vs. just buying an off-the-shelf product? Great question, and one we have strong opinions on because we’ve lived…
Continue Reading

Dear SaaStr: I Want to Roll Out an AI SDR. How Do I Start? First, get clear on what you’re actually buying — and what it actually does. We’ve now been running AI SDRs at SaaStr for over a year. Multiple platforms. Real data. Real pipeline. And the honest answer is: it works. But it…
Continue Reading

Dear SaaStr: Do You Have to Have a Super Strong Brand Like SaaStr To Get AI SDRs to Work? Honest answer: it helps. A lot. But it’s not the thing that determines whether you succeed or fail. Let me explain what brand actually does — and doesn’t — do for AI SDR performance, because I…
Continue Reading

Dear SaaStr: Should I Run 20+ AI Agents the Way SaaStr Does? The honest answer: probably not entirely like us. But you should start now — because the gap between teams who have been running agents for 12 months and those who haven’t is compounding every week. Let us give you the real picture. What…
Continue Reading

Dear SaaStr: What’s the Best Way to Follow Up With a Prospect That Says “I’ll Get Back to You” Let’s start with honesty: “I’ll get back to you” almost always means No — or at best, Not Now. That’s not cynicism. That’s pattern recognition. If a prospect were genuinely excited to move forward, they wouldn’t…
Continue Reading

Dear SaaStr: How Can I Become a Better VP of Sales? The hard truth: most VPs of Sales fail not because they can’t sell, but because they don’t understand what the job actually is. It’s not managing a team. It’s not building process decks. It’s not attending QBRs. It’s making your number — quarter after…
Continue Reading

Dear SaaStr: I made it to the final round for an SDR position at a leading vertical B2B company. The interview is with the Sales Manager. How do I prepare so I actually get this offer? First off — congrats. Making it to a final round SDR interview at a real vertical B2B company means…
Continue Reading

Dear SaaStr: We’ve raised $2M and our investors don’t want to put more money in. We’ve about 7 months of runway. An acquirer wants to purchase us for $4-5M. What will our VCs think of this outcome? I get versions of this question a lot, and I want to be direct with you: your VCs…
Continue Reading

Dear SaaStr: We’re at $4M ARR, growing well, and a lender is offering us $3M in venture debt. Our investors think it’s “non-dilutive capital.” Should we take it? Short answer: Maybe. But understand what you’re signing before you do. Because “non-dilutive” is one of the most dangerous half-truths in startup finance. Let me tell you…
Continue Reading