Dear SaaStr: When Should I Hire Our First Sales Person, and Who Should I Hire?
We’ve talked a lot about this over the years on SaaStr but this is a great chance to summarize it all:
First, you should hire your first salesperson once you’ve closed at least 10 customers yourself.
Why? Because as a founder, you need to understand the sales process, the objections, and what resonates with your customers. If you can’t sell your product, it’s going to be tough to teach someone else how to do it. Plus, customers love talking to the CEO—it builds trust and credibility. So, close those first 10 deals, and then you’ll have a foundation to bring someone in 69.
Now, when it comes to the type of salesperson to hire, here’s the playbook:
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Hire someone you’d personally buy from. This is non-negotiable — and the #1 error founders make. If you wouldn’t trust them with your leads or feel confident they can sell your product, don’t hire them. Early on, your sales hires need to be extensions of you—they need to understand the product deeply and build trust with customers.
- Hire smarter. Smarter alone isn’t enough, but you do need your first 1-2 reps to be true product experts. Pass on anyone that can’t be one.
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Look for at least 18 months of SaaS sales experience. Ideally, they’ve sold a product at a similar price point. For example, if your product is $10K/year, find someone who’s sold something in that range. They don’t need to be a rockstar, but they should know the basics of SaaS sales—pipeline management, cadences, and closing deals. You can’t teach them that, so they can’t operate on their own without it.
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Hire two reps, not one. This might feel expensive, but it’s critical. If you hire just one and they succeed, you won’t know why. If they fail, you won’t know if it’s them or your process. With two, you can compare and learn what works. Plus, sales is a numbers game—having two reps doubles your chances of success early on.
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Be there to support them. In the early days, training is by osmosis. You need to be present, answering their questions, listening to calls, and helping them close deals. This isn’t the time to step back—it’s the time to lean in.
So, close those first 10 deals, hire two reps you’d truly buy from, and make sure they have some SaaS experience. Then, roll up your sleeves and help them succeed. That’s how you set the foundation for scaling your sales team.
And a related post here:
