How to hire your first executive. Stop being the bottleneck.

Are you ready to hire?

Before you write a job description, answer these questions honestly:

• Do you have 12+ months of runway including this hire's salary? If not, pause. An executive needs time to deliver — you can't afford to run out of cash before they get results.
• Have you identified a specific, high‑leverage job to be done? "General help" isn't a role. You need to know exactly what function you're handing off.
• Do you have at least 40 hours of work per week for this person? If not, you're hiring too early.
• Do you know what "great" looks like in this role? If you can't describe it, you can't hire for it.
• Are you willing to spend 20% of your time managing and unblocking this person? Executives don't manage themselves — especially in the first 90 days.

COO vs. VP of Sales

Most founders don't know whether they need a COO or a VP of Sales first. Here's the decision rule:

• Hire a COO if your biggest problem is operations — delivery, systems, team management, execution. You need someone to turn strategy into execution, build systems, manage teams, and own the numbers.
• Hire a VP of Sales if your biggest problem is revenue — you have product‑market fit but can't scale sales beyond founder‑led deals. Don't hire a VP of Sales to validate your market; hire one when you know what's working and need someone to turn it into a machine.
• If both are broken, hire a COO first. A COO can oversee sales operations while you focus on closing; a VP of Sales can't fix ops.

Build the hiring scorecard

A scorecard is a 1‑page document that defines the role's mission, 12‑month outcomes, must‑have skills, and red flags — before you start interviewing. It removes bias, lets you compare candidates objectively, and gives you a framework to give feedback. Without one, you're hiring on gut feel — and gut feel is wrong more often than it's right.

The 4‑stage vetting process

A COO or VP of Sales is too important to hire from a single conversation. Use a multi‑step process that tests operating ability, judgment, and fit in turn — and score candidates the same way at each stage.

• Stage 1: Screen (30‑45 min). Track record, scope of past P&L, and why this role. Ask: "Walk me through your career — what were your biggest wins and why did you leave?"
• Stage 2: Working Session (90 min). A real problem from your business: a 30‑60‑90 day plan, an operations diagnosis, or a scaling challenge. This is your single highest‑value signal — how they think beats how they answer rehearsed questions. Give them your actual data and watch them work.
• Stage 3: Deep References (multiple calls). For an executive hire, references are not a formality — they are the deepest signal you get. Don't just call the people they list. Back‑channel to people who worked with them but weren't their cheerleaders. Ask: "What's the one thing I should know that they won't tell me?"
• Stage 4: Founder Round (60 min). Chemistry and delegation‑trust. You are deciding whether you can hand this person real authority and sleep at night. Be vulnerable upfront: "These are the things I don't have expertise in — I'm hiring someone I can trust to lead them."

The questions that reveal truth

Standard interview questions get standard answers. These questions cut through the polish and reveal how a candidate actually thinks, leads, and operates.

For a COO:

• "What KPIs would you implement in your first 90 days, and how would you operationalize them?"
• "Walk me through a P&L you've owned — what was your scope, and what did you improve?"
• "Tell me about a time you professionalised chaotic processes without slowing innovation."
• "How do you handle disagreements with a CEO? Give me a real example."

For a VP of Sales:

• "Walk me through your first 90 days — how would you assess, prioritise, and build a repeatable motion?"
• "Tell me about the first sales hire you made. What qualities did you look for?"
• "Tell me about a time you had to turn around an underperforming sales team — how did you diagnose and fix it?"
• "What will my revenues look like 120 days after I hire you?"

Pay them right

The right compensation package balances cash to cover their needs and equity to align their incentives with long‑term growth. Here are the benchmarks for $1M–$10M businesses:

• COO: Base salary $140k–$220k depending on stage, with equity of 1–2%.
• VP of Sales (Seed–Series A): Base $140k–$180k, with equity of 0.25–0.5%.
• VP of Sales (Series B/C): Base $180k–$220k, with equity of 0.25–0.5%.

Structure the offer with:

• Base salary — enough to cover their cost of living (use the benchmarks above).
• Equity — vests over 4 years with a 1‑year cliff. This aligns their incentives with long‑term growth.
• Performance milestones — mapped to compensation triggers. For a VP of Sales, this might be revenue targets. For a COO, operational KPIs.
• Sign‑on or performance bonus — use sparingly, but can be effective for competitive candidates.

Set them up for success

The hire is made. Now the real work begins. Your first executive needs a clear 90‑day plan:

• Days 1‑30: Learn. Meet every department head, review every system, shadow every process. No major changes yet — just diagnosis.
• Days 31‑60: Plan. Present a 30‑60‑90 day plan back to you. This is where you see if they truly understood the business.
• Days 61‑90: Execute. Start implementing the first wave of changes. Measure against the scorecard outcomes you defined.

And most importantly: spend 20% of your time managing and unblocking them in the first 90 days. They're not a set‑and‑forget hire — they need you to be available, clear on priorities, and willing to make decisions when they get stuck.