First Sales Hire Guide
Most founders hire their first salesperson too early, into a company with no system, and then wonder why it didn't work. Here's what to build before you hire, what to look for, and how to set your first rep up to succeed.
Build the system before you hire.
The most expensive mistake founders make is hiring a salesperson before they have a Sales Playbook, a defined ICP, and a structured pipeline. Your first rep will figure out their own way to sell — which may not match what actually works. The infrastructure comes first. Always.
Your ICP, discovery questions, demo flow, objection handling, pricing conversation, and follow-up cadence. If this lives only in your head, your first rep will invent their own version of your sales process — which may not work. Write it down first.
Not 'companies who might benefit.' Specific: industry, company size, title, pain point, trigger events that make them ready to buy now. Your rep can only target who you define.
Replace 'Interested' and 'Proposal Sent' with stages that reflect what the prospect has done. 'Discovery call completed. Next step agreed.' This gives your rep a real pipeline they can manage — not a wishful thinking list.
Day 1–30: product immersion, playbook study, shadowing. Day 30–60: managed demos with feedback. Day 60–90: independent deal ownership with weekly 1:1 coaching. Set specific milestones at each phase.
A written document that defines the role, the expected activities, the KPIs, and what success looks like at 30, 60, and 90 days. No ambiguity. Your rep knows exactly what they're accountable for before they start.
When you've closed 10–20 customers yourself and you understand the repeatable pattern. That means you know who buys (ICP), why they buy (pain + trigger), and how the conversation goes from first contact to close. If you haven't closed those deals yourself, you don't have enough pattern to hire into. You'll just be funding someone else's guessing.
For your first hire, almost always full-cycle. An SDR alone generates leads but can't close them. An AE alone can close but needs leads fed to them. A full-cycle rep prospects, qualifies, demos, and closes. At your stage, you need someone who can own the whole motion. Specialization comes later.
Plan for 50/50 base/variable. For B2B companies at the $1M–$5M ARR stage, that typically means $60k–$80k base with $60k–$80k OTE upside for a total of $120k–$160k OTE. The ratio matters: too much base removes the performance incentive. Too little base attracts reps who need quick wins over long sales cycles. Get the ratio right.
Look at activity KPIs, not just closed revenue. In the first 90 days, revenue is a lagging indicator. What you should see: are they running real discovery calls? Are they building their own pipeline? Are they improving their demos based on feedback? Activity plus progression in the playbook tells you more in 30 days than revenue will in 90.
Two. With one rep, you can't tell if results are because of the system or because of the individual. With two, you have comparison data. If one is dramatically outperforming, you learn from them. If both are struggling, the system needs fixing. Two reps also create peer accountability and make each other better. The cost difference is real but the learning is worth it.
Let's spend 30 minutes together. We'll look at where you are now, what needs to be built before you hire, and what the right first hire profile looks like for your specific business.