Hiring Your First Sales Rep: A Founder's Complete Guide

Your first sales rep is one of the hardest hires you will make. You need someone who can sell without a playbook, handle constant rejection, build their own pipeline, and help you figure out your go-to-market strategy, all while being affordable enough for a startup budget.

When to Hire

Do not hire a sales rep until founders have personally closed at least 10-20 customers. You need to understand your sales process before you can hand it to someone else. If you hire a rep before you have any idea what works, you are asking them to figure out your business model for you. That is not their job.

The right time to hire is when you have a repeatable sales process (even if rough), you understand your ideal customer profile, and there is more demand than the founders can handle.

What to Look For

For your first hire, look for two to five years of experience with a bias toward people who have sold similar deal sizes to similar buyers at startup or high-growth companies.

The essential traits are coachability, comfort with ambiguity, resilience in the face of rejection, genuine curiosity about your space, and strong work ethic. The biggest red flag is someone who has only worked with inbound leads. Your first sales rep needs to build their own pipeline from scratch.

Compensation Structure

For early-stage startups, a 60/40 or 70/30 base-to-variable split works best. Too much variable is risky for candidates and you will struggle to attract good people. Too much base removes the incentive to perform.

OTE ranges for 2026: first sales rep at $120-180K, with startup sales experience at $150-200K, with enterprise experience at $180-250K.

The Bottom Line

Your first sales rep should be a learner and a builder, not a process-follower. Look for hustle, curiosity, and coachability over big-company experience and polished pitches.