Dear SaaStr: What’s Your #1 Opener in Sales? The best opener is sharing how a very similar company or a competitor uses your product — and the exact specific ROI that customer gets. Everyone wants to know the playbooks of similar companies and competitors. How often does your sales team actually do this? Put in…
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Dear SaaStr: When should I pay the commission for SaaS sales? All of our trial signups will get an automatic email from an account executive. How do we decide if the AE was responsible for the sale versus the sale just happened organically? Every company with a self-serve component and a sales-driven component frets a…
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Dear SaaStr: What’s the #1 Mistake New Sales Leaders Make? Let me just summarize my #1 observation here: the top mistake first-time sales managers make is recruiting. In that — they can’t do it. They can’t recruit great reps. They can recruit some mediocre ones, but that’s about it. It is incredibly hard to figure…
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Dear SaaStr: What Qualities Make a CEO The Best In Their Industry? I’ve invested in 5 start-ups that had a $1,000,000,000+ cash exit or IPO. The CEOs were all quite different. Some extroverted, some introverted. Some wicked smart, some merely very smart. Some direct, some warm and friendly. But what made them great: Ability to…
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I pitched 150+ entities over the years as both a start-up exec and a founder. And now I’ve been on the other side of far more than 150 meetings as part of SaaStr Fund. Nothing in fundraising really phased me as a founder — for the most part. Except one set of meetings. Raising money…
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Dear SaaStr: What Was The Best Advice You Ever Got From an Angel Investor The best advice I ever got from one of my angel investors: Stop feeling sorry for yourself. I went to meet with one of my angels and mentors when things were probably toughest at my last start-up. My co-founder had walked…
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Dear SaaStr: Did it Ever Take You a Year Or More to Close a Sale? Absolutely. It took us about 18 months to close Google, for example: Need identification and discussions with project manager over several months About 6 on-site meetings to review need identification and discussion with broader group RFP Prototype of workflow Ensure…
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Dear SaaStr: Does a Big Exit Make You Happy? Well here in the SF Bay Area … we live in a strange place. Folks I know with “infinite” money sort of fall into 3 buckets: Category 1: Still Building Stuff. For Whatever Reason. In their DNA. This is who they are. Oftentimes, they aren’t really…
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Dear SaaStr: What do startup founders typically get wrong when starting a business? My list: Not committing to 24 months upfront to getting to Real Revenues and a Minimum Sellable Product. We’ve written about this before, but I see it again and again and again. It takes 7–10 years to build something real, and the first…
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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…
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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…
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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…
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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…
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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…
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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…
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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…
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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…
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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…
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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…
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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…
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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…
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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…
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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…
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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…
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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…
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