Dear SaaStr: What Should I Look For In My Very First Sales Rep?
The first thing to understand is that hiring your first sales rep is one of the most critical decisions you’ll make. It’s not just about finding someone who can sell—it’s about finding someone who can sell *your product* in the stage your company is in. Here’s what to look for:
1. Someone You Would Buy From
This is non-negotiable. If you wouldn’t buy your own product from them, don’t hire them. Early on, your sales rep needs to be someone who can build trust with your prospects and truly understand their pain points. They should be able to architect a solution to those problems, not just push a product. I’ve seen this firsthand—when I hired Joe Coletti at Adobe Sign / EchoSign, he knew the product cold, and customers trusted him. That trust is what closed deals in the early days.
2. The Ability to Learn Your Product Fast. Ideally, Even During the First Interview
Early-stage sales reps need to know your product inside and out. They don’t need to be technical, but they need to understand how your product solves problems better than anyone else. At Adobe Sign / EchoSign, we lost deals to DocuSign early on because some of the reps we hired didn’t know the product well enough. They couldn’t articulate why we were better, and it cost us.
3. Proven Ability to Thrive in Chaos
Look for someone who has worked in environments where they didn’t have all the resources handed to them. Maybe they’ve been the first rep at another startup or have experience in a scrappy, entrepreneurial setting. These are the people who can figure things out without needing a playbook handed to them.
4. A Track Record of Hustle. Ideally, At Somewhere Hard to Sell.
I love reps who’ve done something hard before—whether it’s selling Cutco knives door-to-door or working in a tough outbound sales role. These experiences build resilience and grit, which are invaluable in the early days when leads are scarce, and every deal matters.
#5. Be Very Wary of Folks That Have Only Worked at a #1 Player in a Space
They just don’t know how to sell in at a start-up that not only isn’t #1, but doesn’t even have a mini-brand yet. But that scrappy AE who crushed it at a #3 player in a space? Gold.
#6. Someone Who Can Be Your Sales Right Hand
In the early days, your first sales rep is almost like a co-founder in the sales function. They need to be someone you trust implicitly and can work closely with. You’ll likely need to micromanage a bit at first, so they should be comfortable with that dynamic.
7. Don’t Overvalue Resumes
A flashy resume from a big-name company doesn’t mean much if they’ve never sold in a startup environment. Everyone has seen reps from Salesforce or other big companies fail miserably in startups because they were used to having all the resources and brand recognition that come with a large organization. Early-stage startups are a different beast.
Finally, hire slowly and carefully. Interview 30 people if you have to.
There’s probably only one or two out there who are the right fit for your stage. And when you find them, don’t hesitate—hire them. They’ll be the ones who help you get to the next level.
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