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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Jason Lemkin led the seed round via SaaStr Fund in unicorn Owner.com, an AI solution revolutionizing how small restaurants manage their business. Kyle Norton joined shortly thereafter, and after a slow few months, Kyle rocketed the org to almost $100m ARR in just a few years — with growth accelerating at scale. Both Kyle and…
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At SaaStr AI London, Amelia and I went deep on our AI SDR journey. We shared all our data, all the emails we’ve sent, all the performance metrics—everything. And the response was overwhelming. But here’s the thing: the #1 objection we kept hearing was “Yeah, but this won’t work for me. I don’t have your…
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So with the end of the year coming up again, it’s time to once update a classic SaaStr post. It may even be our official SaaStr Holiday post, really. On why the best sales teams just close so much on the last day of the year (be it Dec 31 for many of you, Jan…
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What I Learned From a Packed AMA at SaaStr AI London 2025 I did an open AMA at SaaStr London last week, a classic part of each SaaStr AI event. But this one was different. It was urgency to the max. The room was packed with founders, CROs, and marketers who all seemed to be…
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Dear SaaStr: If you were hiring a head of sales for a high-priced, niche B2B SaaS product, would you focus on general B2B SaaS sales experience or on market/customer knowledge, assuming it will be very difficult to find a candidate with both? This is the scenario when the trade-off is the most acute. Imagine you…
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A mistake many founders make is hiring a VP of Sales who has many strengths — but is not great at selling themselves per se. A VP of Sales who is smart, polished, and worked at the right place, in a management-level position. That can talk about quota attainment and sales operations and scaling and…
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After deploying 5 AI SDRs across inbound, outbound, and follow-up—here’s the actual numbers, unexpected learnings, and what it really takes to make them work Six months ago, we had essentially zero AI SDRs at SaaStr. Today, we’re running five specialized AI agents that have sent nearly 20,000 outbound messages, closed over $1M in revenue, and…
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Dear SaaStr: What Did You Do in Your Startup That Didn’t Scale? My list is a bit quirky, but perhaps it will help a few others to accelerate — or drop — a few things: Doing international customer support myself. For months, I did European customer support myself rather than hire someone. This was just…
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