All Posts

February 27, 2026 ยท Louie Bernstein

Why You Hire Two Salespeople First

hiringfounder-led sales

Here's something I've learned as a Fractional Sales Leader over the past nine years: 1 = 0 in hiring your first salesperson. Here's the math behind why so many solo hires fail.

Most founders hire one salesperson to start. They view it as a linear cost. One salary equals one sales-producing sales person. Start counting the sales! Not so fast.

Hiring only one salesperson creates a blind spot for a CEO trying to transition out of founder-led sales. - You have no data. - You don't know if your onboarding is bad or if the rep is lazy. - You don't know if the quota is realistic. Without a peer to compare against, a mediocre rep looks okay.

Change your hiring roadmap. Start two salespeople at the very same time. Give them the exact same sales playbook. Then...

- Watch who watches the training videos. - Watch who makes the first call. - Watch who asks for help.

Here's a few more reasons to hire two salespeople instead of one: - If one quits, you don't have to start from scratch again. They can help train each other. - It can foster healthy competition. - You might get your first sales manager from one of the two.

Do you have a scorecard ready for two candidates? If not, founders only - book a call for my scorecard. I'm a Fractional Sales Leader and I've done this many times before.