Home When (and How) to Hire Your First Salesperson - A Founder's Guide
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When (and How) to Hire Your First Salesperson - A Founder's Guide

The Foundation First

Before you even think about hiring a salesperson, there’s one critical truth you need to accept: you must establish market validation for your product. Salespeople need something concrete to sell, not just promises and PowerPoint decks.

The Product Must Be Ready

Your product should be:

  • Clearly defined
  • Well-packaged
  • Repeatable in its sales motion

Warning: The Danger of Premature Sales Hiring

When salespeople lack a solid product, they often resort to:

  • “Selling the deck”
  • Making promises they can’t keep
  • Creating fictional features

This leads to two painful outcomes:

  1. Unwinding deals and losing revenue
  2. Compromising your product roadmap to meet unrealistic promises

The Founder’s Role

“If you can’t define it well enough to sell it to a customer, then nobody can.”

As a founder, you must be able to:

  • Sell your product effectively
  • Define your target market
  • Understand who wants to buy it

Bonus question: How can you convince investors if you can’t convince customers?

The Right Way to Onboard Your First Sales Hire

1. Create a Strong Partnership

  • Make them your commercial lead
  • Position yourself as their sales engineer
  • Stay involved without micromanaging

2. Evolution of Roles

Graduate to being a “closer”:

  • Let your salesperson set up opportunities
  • Step in for the final close when needed

Aligning Incentives

Remember:

  • Tie compensation to company goals
  • Include strategic objectives, not just revenue
  • Understand that good salespeople optimize for reward/effort ratio
  • Use this to your advantage

The Money Question

Important rules about compensation:

  • Pay market rate or don’t hire
  • Avoid “budget” salespeople
  • If you can’t afford top talent:
    • Keep selling yourself
    • Raise capital once you have product-market fit

Required Reading

📚 Essential Resource: “The Hard Thing About Hard Things” by Ben Horowitz

  • Focus on the section about hiring the first head of sales
  • Read it multiple times until the lessons stick

Remember: A great salesperson can accelerate your success, but only if you’ve laid the proper groundwork first.

This post is licensed under CC BY 4.0 by the author.