Never hire anyone in sales that doesn’t care about money You’ll see — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) June 24, 2025 So you’re hiring your first few sales reps in the early days? Before you have a great VP of Sales? It’s an interesting time. Leads are precious, everyone is a team. So you need a very certain type of sales rep. Let me give you a checklist of a few signs they won’t work out: #1. They’re Late Many will challenge me here, but if they’re late to the interview, they’ll be late to customer calls, too. Don’t make the hire. If they send you a professional message ahead of time, that they need to push? That’s fine. If they just show up at 2:05 onto the Zoom though, don’t make the hire. #2. You Wouldn’t Buy From Them A classic SaaStr theme, as true today as it ever was. If you honestly wouldn’t buy from them — well neither will your prospects. At least not in the early days. Not during founder-led sales. “The #1 key to hiring your first few sales reps: They HAVE to be folks you’d honestly, truly, really buy from yourself. That you’d buy your own product from. For real. This is the 1 corner you can’t cut. Maybe the only corner you can’t cut.” with @lennysan pic.twitter.com/LnYL7FZ1LG — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) August 3, 2026 #3. They Can’t Sell You This Pen I don’t know if these days, a sales rep has to come to the first interview being able to do a strong sales demo of your sales product. But at least make sure they can do it before you send over an offer. #4. They Don’t Do Any Research Before The First Zoom Too many folks phone it in and do zero research before a “Learn More” meeting. They’ll phone it in before they meet, prospects too. Or worse. #5. They Struggle With Your Tech If they can’t get your Calendly or Mixmax link to work, if they struggle to get Zoom to work … well … I get it. But they’re gonna struggle to understand and sell your product, too. #6. They’ve Also Got Another Job I know a lot of folks want to work 2 jobs at the same time today, or 2-3 additional big side hustles. But I’ve just never seen early sales rep excel that do this. It’s too intense, you have to be a product guru as an early rep. You don’t get there if your mind is also focused on all your other jobs and businesses. Can you still “sell”? Sure — if it’s very transactional. But it’s never that simple or easy in the early days. If ever. #7. They’re Really Angry About Their Last Role Almost every great sales exec I’ve ever worked with has had one tough role. Many of the best have been fired once. But if they are too bitter in the interview? They’ll be just too sour once they start. #8. They’re Constantly on LinkedIn. Like Posting Multiple Times Every Day, Constantly. A little of this is OK. But if they are spending tons of time promoting themselves, their experience, their courses, etc. on LinkedIn — be wary. You want a hunter. Someone that wants to close deals and make coin. Not be an influencer. Hunters don’t have interest or time in being LinkedIn influencers. #9. Your Product is Just Much More Complex Than The Other Ones They’ve Sold There are rare exceptions here, but in general, sales execs just struggle to sell much more complicated product than they’ve sold before. By contrast, they can fly if you put them in an environment where the product is simpler and easier to sell. Be way if you’re in vertical SaaS or complex fintech or developer-focused tools hiring folks that have only sold, basically, to folks like themselves. They can wing that. They can’t wing environmental compliance sales to a Chief Compliance Officer. #10. They Aren’t Focused On Money Sales is about a lot of things, but making money is one of them. If they’re not focused on making money, they may be good at something. But it’s likely not sales. Ok that’s my checklist. Many will challenge parts, or disagree. And a great VP of Sales can take more liberties here. They have time to manage folks more than founders do. But in the founder-led sales days, pass on these folks. Just keep interviewing. A related post here: How to Ensure Your First 2 Sales Reps Actually Work Out (Updated)
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