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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The CEO of an AI Agents company we genuinely admire reached out recently and asked why we didn’t select them as a vendor. It was a fair question — they have a great product. The honest answer? Their VP of Sales argued with us. Wouldn’t do any work up front. Wouldn’t give us access to…
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We’ve been running AI GTM agents for almost a year now. We use Artisan for outbound, Qualified (now Salesforce) for inbound, Agentforce for Salesforce-native outreach, Delphi for Digital Jason. We’ve sent 20,000+ AI messages and generated over $2M in closed revenue from our AI SDR on its own (plus much more where AI SDR set…
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Dear SaaStr: Should sales reps be compensated differently based on how much prospecting they do? For example, if all of their leads come inbound (without effort on their part) should they receive a lesser % per deal vs a rep that prospects for their own leads? It often makes sense to pay reps more from…
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Dear SaaStr: Should We Pay Our Sales Reps on Renewals? Simple answer: most don’t. You can, especially in the early days. But very few SaaS companies pay sales reps on renewals as they scale. And you can definitely pay on upsells and account expansion. Longer reason: most SaaS companies don’t pay AEs on renewals —…
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Dear SaaStr: Is It Worth Working as a Sales Rep? Absolutely. Being a sales rep is the hardest job that almost anyone can get and at least try to do. But boy, you will learn. You will learn: How to hear “No” 100 times in a row. If you can turn 100 “No’s” into 1–2…
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Dear SaaStr: What’s The Best Way to Get Traction After We Have A Few Paying Customers? Answer: try everything that just might work, even a little bit. Then: double down on anything that works even a little. That may sound obvious, but what I mean is, most start-ups scale roughly the same way after $1m-$2m…
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The classic sales plays do still work. Hard work, knowing the product cold, showing up. But the classic 2021 playbook? It’s close to dead in the Age of AI. And here’s one example of why. The other day I did something that should make every sales rep reach for the keyboard: I reached out directly…
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Team SaaStr has been living in AI and sales for the past 18 months, but things really accelerated started around June 2025 Since then we’ve deployed 20+ AI agents at SaaStr. Our AI SDRs now send 11-40x the volume of our human SDRs—with better results. Our AI inbound agent has closed over $1M in revenue…
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I saw about 10 CROs leave or get fired this year across the startups I work with or have invested in at SaaStr Fund. That’s a lot. That’s actually a ton. It may be a record. I suspect it is. And look, some CRO transitions are natural. The company outgrows them. They want to go…
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