Dear SaaStr: Should I Remove Monthly Subscriptions to Drive Down Churn? Generally — no. Annual plans only mask churn. They don’t eliminate it. And at least for SMBs and prosumer customers, not having a monthly edition can add significant friction to buying. That means less customers & less sales. I’s a double-edged sword. It simplifies…
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Dear SaaStr: Should We Over-Charge or Under-Charge our First Customers? My general rules: Overcharge if the customer is big, i.e., >$50k-$100k a year o nor so in ACV. Undercharge if the customer is smaller by revenue. There’s a method to the seeming madness here. You’re learning very quickly here if you are enterprise or mass-market…
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Dear SaaStr: What’s It Like to Have Your Company Acquired by One of the Tech Giants? It’s a lot of change. The pressure is mostly or at least partially off. Unless there is a huge earn-out or retention payment tied to performance, the pressure is off. Not all of it. But the insane founder-CEO pressure you…
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  Dear SaaStr: How can I boost my sales if I am in B2B sales? My top tips for AEs: Grab your CEO and bring her into bigger deals. Ask your CEO to join you on a few sales calls a month. Deals will close at a higher rate if the CEO joins. Customers love…
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The biggest mistake you can make as a founder when you hire your first VP of Sales is stepping out of sales I see this again, and again It only works with the very best VPs of Sales Every other first VP of Sales needs you doing at least half of what you were doing…
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The top one for me is when they don’t embrace the goals given to them. Sometimes it’s subtle, sometimes it’s aggressive and overt. What I see this again and again: A VP of Sales that just sort of ignores the plan for the next quarter or two. A CMO that focuses on the types of…
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Dear SaaStr: I’ve Been Out of Sales For 6+ Years. Is It Too Late to Get Back In? I stayed at home as a parent and then played professional poker for several years. Ok here’s the thing: you have 2 flags already (and staying home for the kids isn’t one of them). Issue #1 isn’t…
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Dear SaaStr: What are some benefits you can add to get people to buy a product besides discounts and add-ons? You can help them actually deploy your app. To actually, truly get the value out of it. Not just buy it. Buying a product is just Step 1, at best. Mediocre sales reps focus way…
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Dear SaaStr: What’s the #1 Most Important Thing To Look For In Your First Sales Rep? The #1 most important criterion for your first 2 reps is: would you buy from her? For real? Would you truly, 100%, buy your own product from them? 98% of the reps you interview … will fail this test….
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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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