Hiring your first sales reps and handing off founder-led sales

Why curiosity beats closing instinct

Early-stage selling is mostly discovery. Your rep needs to understand the customer's problem better than the customer does, and that comes from asking good questions and actually listening to the answers. Curious people do that naturally. They also pick up the product, the competitors and the market faster, which matters when there's no enablement team to teach them.

In interviews, I'd suggest asking candidates to run a short discovery call with you. Watch how many questions they ask, whether they follow up on your answers, and whether they understand your problem before they start pitching.

The team structure I like

I've had the best results hiring one strong traditional salesperson first, someone who's carried a number and knows how to run a full cycle. Then I build two or three junior reps around them who have high ceilings: smart, hungry and coachable. The experienced rep sets the standard and helps coach, and the junior reps grow into the role at a cost that makes sense for an early-stage company.

Handing off founder-led sales

The handoff is where a lot of companies lose momentum. The founder knows the product, the customers and the story better than anyone, and that's hard to transfer. The key is to write down what's in your head before the first rep starts:

• Who your best customers are and why they bought.
• The questions you ask on a first call.
• How you demo and what you leave out.
• The objections you hear most and how you answer them.
• What you charge and when you discount.

How to know it's working

In the first 90 days, judge new reps on activity and pipeline quality more than closed revenue. Are they booking meetings, running good discovery and getting clear next steps? From there, you can hold them to a number once they've had a full sales cycle to work with.