Why first sales hires fail
You hired a salesperson to take over selling. Three months later, they haven't closed a deal. Six months later, they're gone. You wonder if you hired wrong — but the next one fails too.
Take the assessmentWhat you're seeing
The pattern looks like a hiring problem. You bring in an experienced salesperson, they seem great in interviews, but they can't close. They blame the product, the market, the leads. You blame their skills. You're both wrong.
What's actually broken
First sales hires fail because they're asked to do two jobs at once: figure out the sales process while also executing it. Founders can sell because they have deep product knowledge, customer insight, and the authority to improvise. A new hire has none of that. They need a documented, repeatable process to follow — and most founders skip this step. The real gap is repeatability: if you can't describe why deals close and document the steps, nobody else can sell your product.
Fix it in this order
- 1.
Document before you hire
Write down your sales process: stages, typical timeline, common objections, qualification criteria, and why your last 5 deals closed. This is the playbook your hire will use.
- 2.
Test the documentation
Have someone unfamiliar with your product read the playbook. If they can't explain your sales process back to you, it's not documented enough.
- 3.
Set 90-day expectations
A good first sales hire should close at least one deal in 90 days using your documented process. If they can't, either the process isn't ready or the hire isn't right.
- 4.
Stay involved early
Plan to ride along on the first 10 calls. Not to close for them, but to identify where the documented process breaks down with a different person running it.
Explore the root causes
Related problems
Frequently asked questions about why first sales hires fail
- When is the right time to hire my first salesperson?
- When you can answer three questions: Do you have a documented sales process? Can you articulate why deals close? Do you have enough pipeline to keep someone busy? If any answer is no, you're hiring someone to figure it out — and that rarely works.
- Should I hire an experienced closer or a junior rep?
- Neither is right if the process isn't documented. With a playbook in place, a junior rep with good coachability often outperforms an expensive closer who has their own way of doing things. The first hire needs to follow your process, not invent their own.
- What if I can't afford to wait — I need revenue now?
- If you can't afford to wait, you definitely can't afford a failed hire. A bad sales hire can easily cost six figures when you add up salary, recruiting, ramp time, and the deals they didn't close. Spending 2-4 weeks documenting your process is the fastest path to a successful hire.
- How do I know if the problem is the hire or the process?
- If the salesperson can describe your ICP, articulate your value prop, and handle common objections — but still can't close — the hire might be wrong. If they can't do those things, the process documentation is the problem.