The #1 Mistake Founders Make When Hiring Their First Sales Rep
You've achieved product-market fit through pure founder-led sales. Now, it's time to scale. You hire your first "rockstar" sales rep, someone with a great resume from a well-known company. You expect them to come in and start printing money. Three months later, they've closed almost nothing, and both you and the rep are frustrated. What went wrong? The mistake happened long before you hired them. You hired a player before you built the field.
A new sales rep looking confused at a desk with no computer or playbook.
You Hired an "Executor" to Do a "Creator's" Job
Most experienced sales reps from established companies are brilliant executors. You give them a territory, a playbook, a CRM full of leads, and a quota, and they will run the process flawlessly. The problem is, in an early-stage startup, that process doesn't exist yet.
You, the founder, have been running sales on intuition, passion, and deep product knowledge. Your "process" is in your head. You haven't documented it. You haven't turned it into a repeatable system. You hired a chef and gave them a kitchen with no recipes. You are asking an executor to be a creator, and that's a recipe for failure.
The Prerequisite to Your First Sales Hire: The "Sales Playbook v0.1"
Before you even write the job description for your first sales rep, you must have a "Sales Playbook v0.1." This is not a 100-page document. It's a simple, scrappy set of instructions that codifies what has worked for you so far. It must include:
You cannot hire someone to create your sales process. You can only hire someone to run and improve a process you've already proven.
- A Hyper-Specific ICP Definition: Who are your best customers? Not "SMBs," but "US-based B2B SaaS companies with 50-200 employees that use HubSpot."
- Your Core Messaging: What is the exact email sequence you used to get meetings? What is the phone script? What are the top 3 pain points you solve?
- Objection Handling: What are the top 5 objections you hear, and how do you respond to them?
- A Simple Tech Stack: What tools are you using? A CRM? A sales engagement tool? Document the basic workflow.
- Baseline Metrics: What is your current reply rate, meeting booked rate, and close rate from your own efforts? This is the benchmark your new hire needs to meet and beat.
Hire a "Process Improver," Not a "Process Creator"
Your first sales hire's job is not to figure out how to sell your product from scratch. Their job is to take your proven, albeit messy, playbook and do two things: 1) Execute it more consistently than you can, because it's their only job, and 2) Systematically improve it. They should be testing new messaging, refining the ICP, and improving the conversion rates at each step.
When you interview candidates, don't ask "How would you build our sales process?" Ask, "Here is our current process and our metrics. How would you 2x the results in your first 90 days?" The first question asks them to be a magician. The second asks them to be a salesperson.
Conclusion
The transition from founder-led sales is a critical and dangerous inflection point. Don't fall into the trap of outsourcing the creation of your sales motion. Do the hard work first. Prove the process yourself, even on a small scale. Document it. Then, and only then, hire someone to run it, scale it, and make it better.