Dear SaaStr: How Long Should You Give a New Sales Rep? The tough truth is from 0.5–1.5 sales cycles. And yes this is true even in tougher times. Probably even more so in tougher times. Sales is tough. It’s a lot of Nos to get to a Yes. And while sales is pretty similar in…
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We’ve talked a lot on SaaStr over the years about all different types of VPs of Sales. From Stretch VPs to stage-appropriate VPs. A great checklist here to make sure you’re making the right hire. It’s worth also focusing on a related, high-level point. Especially if you sell to multiple customer segments (i.e., small, medium,…
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I was at a board meeting for a fast-growing AI + B2B startup that just crossed $100m+ ARR and brought on a VP of Sales. He was exasperated. “The good news? Everyone wants to buy. The bad news? They aren’t sure what they want in AI next year. So no one wants to sign a…
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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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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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What I see CEOs at struggling start-ups do: – Go dark– Hide– Lash out– Tweet about lots of things non-work– Invest time on tiny expenses– Argue internally What should do: – Be Present– Be Honest– Be the Rock– Be Realistic/Optimistic You just plain grow faster that way — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) April 13, 2026…
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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 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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ICONIQ just published their State of Go-to-Market in 2026, based on a January 2026 survey of GTM executives at 150+ B2B + AI software companies. The data is always good, Iconiq invests at the growth state in a large cross section of the best in B2B + AI. Here are the 10 findings that matter…
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Dear SaaStr: Is There Any “Con” In Giving Our Sales Tool For Free to Early-Stage Startups? Free can absolutely work. Done right, it’s built some of the biggest companies in B2B + AI: ChatGPT. Claude. Cursor. Slack. Zoom. Canva. Notion. Figma. Almost every AI video generation tool out there. All built massive businesses on the…
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Dear SaaStr: At What ACV Can We Afford a Sales Team? The short answer hasn’t changed much: it’s still tough to afford a human sales team below $299 a month / $3k a year ACV. At least in the U.S. and Western Europe. The math just doesn’t bend enough. But here’s what has changed: AI…
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Dear SaaStr: If We Have Two Overlapping Products is it Better to Have One Sales Team or Two? It’s almost always better to have different sales teams handling different products Why? If for no other reason — Incentive Alignment. Sales reps work on commission, and they are driven almost entirely by what they get the…
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Why Covering Up Declining Customer Growth is the Beginning of the End I’ve seen this movie play out dozens of times now across hundreds of B2B companies. And it almost always ends the same way. The #1 conceit in B2B — the thing that kills more companies than bad product, bad timing, or even bad…
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Raise prices on existing customers,Doesn’t help if you are growing quickly. Just makes them unhappy. Raise prices on new customers,Forces you to deliver more value. Often makes everyone more happy. — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) April 7, 2022 Dear SaaStr: How Do You Change the Price of Your SaaS Product Without Upsetting Existing Customers? My…
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Dear SaaStr: What are some best practices for selling a new product/service to your existing SaaS clients? First, make sure your NPS is high. And drive it even higher. Here’s the bottom line: if your NPS is say > 40 or so, a significant portion of your customers love you. If your NPS is say…
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