Who To Hire First In Sales (And Who Not To)
- Dave Hanley
- Jun 20
- 3 min read
Hiring your first salesperson is one of the most important moves you’ll make as a founder…and one of the easiest to get wrong.
The right hire unlocks growth.
The wrong one costs you months of momentum and a pile of wasted cash.
After building 3 businesses and working with dozens of startups, I’ve seen the same mistakes come up again and again. If you’re a founder wondering how to hire your first salesperson, here’s what you need to know.
1. Most Founders Hire Too Soon
If you haven’t closed a few deals yourself, you’re not ready.
Founders often try to outsource sales too early, hoping someone else will “figure it out.” But early stage sales is all about discovery. Learning what resonates, who the real buyer is, and how to price your offerings. No one can do that better than you.
Rule of thumb: Don’t hire your first rep until you’ve closed 5–10 deals yourself.
The other key aspect of this early sales experience as a founder is to document the process. Too many times, I’ve seen founders try to make their first sales hire without any inkling of a playbook in place. This doesn’t need to be overly formal or fully baked, but you need some best practices to turn over to your first salesperson as a starting point.
2. They Hire the Wrong Type of Person
Startup sales is messy. It’s a blank canvas. You need someone who can build the plane while flying it…not just run it.
That means your first sales hire should be a builder, not just a “closer.”
Big-company reps or junior SDRs are usually the wrong fit. You need someone who thrives in ambiguity, wears multiple hats, and is excited to help define the playbook.
3. They Don’t Know What to Look For
A strong first sales hire is part salesperson, part product champion, and part ops lead.
You’re looking for:
Experience in early-stage sales
Comfort working without a set process and playbook
Curiosity and customer obsession
A collaborative, entrepreneurial mindset
The ability to learn from failure without getting frustrated
This is someone who will shape your culture and go-to-market motion for years to come. Don’t just hire fast…hire right.
Finding and hiring this person is not an easy task. What makes it even more difficult is that there are some salespeople who are only good at selling one thing...and that's themselves.
So I’ve built a free guide which walks you through the exact process you should use to give yourself the highest probability for success.
You can download it here:
Inside, you’ll learn:
How to determine whether a candidate is a builder or a BSer
The proven hiring methodology to land an amazing first sales hire
The red flags you need to know that signal a bad fit
Smart interview questions that help you find a superstar
If you're serious about scaling your startup the right way, this guide will help you avoid the expensive, painful lessons most founders learn the hard way.
Download a free copy here to help you find a builder (and avoid hiring a BSer).
