Dear SaaStr: What’s The Best Way to Set Targets for the Sales Team? First, I try to model 3 overall plans for the year: C-90, C-60, and C-10, not just for the sales team, but the whole company. The C is for “Confidence”. The odds you think you can hit it, from the CEO’s perspective. …
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Churn is not a GAAP metric. It doesn’t have a universal definition. Public companies and startups all seem to define churn differently. And even hide it in part, by doing so. I learned this myself starting out as a B2B CEO. I compared us to the only public company in our space, back in the…
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Dear SaaStr: Is It Normal to Feel Like a Pest When Prospecting for Customers For a Startup? Yes. Most of us will feel like a pest when we start doing outbound. So … get better at it, get over it, and hire folks who know how to do it. Sales is hard. It’s being told…
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In a recent Workshop Wednesday, SaaStr Founder and CEO, Jason Lemkin sat down to discuss 9 signs a startup isn’t going to make it.

There’s an argument going around right now that sales isn’t as important as it used to be. Still important. Just not as much as it once was. Bear with me here. It’s not an argument I agree with. But I can’t argue with the logic. The point is this: the world has bifurcated. And what…
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Dear SaaStr: What are the best 5 tips to improve poor sales performance? If you've never listened to your sales reps' calls, Especially the ones that are mediocre performers, You'll often be shocked what you hear. — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) February 9, 2024 Here are my 5 simplest ideas to quickly improve sales performance. …
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You’d assume Anthropic, of all companies, would be running on some self-grown, cutting-edge AI-native sales platform. Maybe a Salesforce killer they built themselves. Maybe Claude baked into the protocol layer of every workflow. They aren’t. At least not yet. Claude is baked into their stage, it’s the substrate. But it’s used to connect to the…
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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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I'd say about 66% of founders step back from sales when they hire a VP of Sales 95% of the time, it backfires You don't get that time back. You just use it in different parts of the sales process. — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) May 27, 2026 So much of classic SaaStr content is…
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Dear SaaStr: Can salespeople really get customers to buy a product they don’t need right now? Yes, at least up to a point. In many ways, getting folks to buy a product they don’t truly need today is the true art of sales. If they really, truly needed it right now … all you really…
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A while back on LinkedIn and Twitter we had over 200,000 views and engagements on a quick post on “The Magical Sales Rep”, and another 500+ likes on a follow-up. It’s worth a deeper dive. Especially now in 2026, where the role of that first rep has shifted in the Age of AI. And is…
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At SaaStr AI 2026, Kyle Norton, CRO of vertical AI leader for restaurants Owner.com, walked through how his team is generating outcomes that look almost impossible on paper for traditional B2B. Owner sells vertical AI to independent mom-and-pop restaurants (think HubSpot plus Shopify for the corner takeout spot) and they’re at ~$100M ARR growing triple…
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Dear SaaStr: Should a Startup Founder Handle Sales Themself When First Getting Started? The answer is yes – 95% of the time. The “best” sequence for building a repeatable sales engine is roughly: The CEO/founder should close at least the first 10 (or 20 or whatever) customers. That way, she knows. She knows the process,…
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I wrote a version of this post some time ago, and I think it’s really one of the most important posts on SaaStr of all time, so I wanted to update it, especially in these times of more scrutiny and less capital. Because many of you are wondering … should I let my VP of…
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So one of the parts of sales that will likely drive you a bit nuts as a founder is FUD and Counter-FUD. What’s FUD, if you haven’t heard the term before? Fear, Uncertainty, and Doubt. Winning a deal vs. a competitor by getting the prospect to worry about the competitor. Often by stretching the truth…
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