Hiring your first sales reps isn't about finding people who can follow a script. It's about finding people who can create momentum when there’s no playbook, no brand recognition, and no easy inbound leads.
As someone who’s built sales teams from scratch to scale, I've seen it all. Here’s my advice for any founder or sales leader making those crucial first hires.
Why founders should write the first sales playbook
A lot of founders try to shortcut it: hire a Head of Sales, hand them a product, and wait for revenue. In reality, the founder needs to build the first version of the sales motion.
Not a 20-page "playbook" no one reads—but a real understanding of the anatomy of a win:
- What steps actually close deals?
- Where do prospects get stuck?
- What objections matter (and which are just noise)?
If you haven't sold your own product yet, you’re not ready to hire someone else to do it for you. Without that firsthand experience, you can’t coach future reps or spot where deals are dying.
What to look for in your first sales hires
Forget the big-name logos on resumes. Early sales hires aren’t order takers. They’re builders.
Sean looks for three traits above all:
- High curiosity: They ask questions that show real thought.
- Low ego: They're not fragile when things get messy.
- A chip on their shoulder: They want to build something, not just join something.
Sometimes the person with the fancy resume isn't who you want. You want someone who's hungry. Someone who wants to leave their mark.
I recommend hiring two early sales reps whenever possible. Not just for competition, but to quickly spot whether success or struggle is about the person or the process.
Team goals first, then individual goals
Early on, I suggest setting team goals instead of individual quotas.
Early-stage companies don’t know yet what a ‘good’ sales number is. You’re still figuring it out.
Team goals:
- Create shared urgency
- Build culture early
- Mask some of the randomness while you figure out what’s repeatable
But this only works for a limited time. You usually move to individual quotas within the first year. Once you have enough data, you need clear individual accountability.
And above all: keep compensation simple. If your rep needs a calculator to figure out if they can pay rent, your plan is too complicated.
How to onboard new sales hires
Sean is clear about what the first month should look like:
- Week 1-2: Full product training. Learn the tools. Meet the team. Absorb everything.
- Week 3-4: Start generating your own pipeline. Shadow calls, study top reps, reach out cold. Get feedback quickly.
Speed to first real conversation is everything. Don’t wait for leads to land in your lap.
How to spot a bad sales hire fast
You’ll usually know within the first 90 days if someone isn't the right fit. I watch for:
- Lack of pipeline generation
- Not asking for coaching
- Blaming missing resources instead of finding solutions
There’s a difference between a skill gap and a will gap. You can coach skills. You can't coach hunger.
Why firing fast matters more than ever
Today’s market is tougher. Buyers are cautious. CFOs want a line-by-line justification for every dollar. Sales reps who thrived during the easy times may struggle now.
Many reps just aren’t ready for the discipline and resilience modern sales requires. If someone can’t adjust, you have to move quickly.
Build hunters before you build farmers
My advice is hopefully crystal clear:
- Early sales teams need hunters; people who create deals from nothing.
- Later, you can specialize with farmers who grow existing accounts.
If you hire a team of farmers first, you’ll stall before you ever have a customer base to farm. Building a true sales engine starts with people who know how to hunt...through the noise, the rejection, and the lack of brand.
