You're here when: You're closing deals but spending all your time on sales. The product and company need your attention elsewhere, and you're wondering if it's time to bring in help.
The Heuristic
- Have you personally closed 10-20 deals? If not, keep selling. You don't have enough pattern recognition to build a playbook, and without a playbook, a sales hire will flounder.
- Can you describe your sales process in a document a stranger could follow? The trigger, the discovery questions, the objections, the pricing, the close. If this doesn't exist yet, you're the playbook. Hiring someone to replicate what's in your head doesn't work.
- Have you reached traction on the Sales Learning Curve? A useful benchmark is revenue per rep at roughly 2x their fully loaded cost. Before that, you're still in the "initiation" phase, where the entire company is learning how customers buy your product. Hiring aggressively before traction means paying people to sit through a learning process you haven't finished yet.
- Is your product stable and your audience defined? Don't hire a salesperson if your product is still buggy or hasn't found product-market fit, and don't hire until you've locked down your customer persona. A great rep with a broken product churns out refunds. A great rep with an undefined audience wastes cycles on the wrong buyers. You also need a lead generation process in place before the hire starts, so they have something to work with on day one.
- Match the first hire to the stage. If you're making the first non-founder sales hire and the motion is only just becoming repeatable, hire a full-cycle AE / "Renaissance Rep" first. If the motion is already repeatable and you expect to build a small team soon, hire a player-coach sales director first. "Hire one to hire ten" matters once you're actually ready to hire ten.
- AEs before SDRs. Validate the outbound motion with full-cycle closers first. Adding a lead generation layer before the sales motion is proven just creates noise without signal.
- Recruit sales directors via outbound, not job postings. The higher the role, the less likely they respond to ads. The best sales directors are employed and performing well. You have to go find them.
Quick Example
What usually happens: founders who hire a sales rep before documenting the playbook end up micromanaging that rep into doing exactly what the founder would have done, but worse. The rep doesn't understand the product, the customer, or the "why." The founder spends as much time managing as they saved by not selling. The unlock happens when the founder writes the playbook first, then hires someone to run it.
The Anti-Pattern
The VP of Sales Mirage. Hiring a VP of Sales from a big company and expecting them to build your sales motion from scratch. That VP was effective at running an existing machine with brand recognition, inbound pipeline, and established processes. None of that exists at your startup. Also: your best closer is not necessarily your best sales manager. Those are different skills. Promoting your top rep to manager often means you lose your best seller and gain a mediocre manager.
Written with ❤️ by a human (still)