The complete playbook for hiring your first COO or VP of Sales — scorecards, interview vetting processes, and compensation packages for founders who are stuck in the day-to-day.
Your calendar is full of meetings you shouldn't be in. You're still the best salesperson on the team, closing deals you should have handed off months ago. You're managing operations, signing off on every decision, and wondering why you can't get past $5M.
This playbook fixes that. It's built from the patterns we've seen work across hundreds of $1M–$10M businesses at Acquisition.com — and the mistakes that sink founders who don't have a system.
Before you write a job description, you need to know exactly who you're looking for, how to find them, and how to structure the deal so they stay.
Step 01 // Readiness
Do you have 12+ months of runway including this hire's salary? If not, pause. An executive needs time to deliver.
Have you identified a specific, high‑leverage job to be done? "General help" isn't a role.
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.
Step 02 // Role
Hire a COO if your biggest problem is operations — delivery, systems, team management, execution. You need someone to turn strategy into execution.
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.
Step 03 // Scorecard
A scorecard defines the role's mission, 12‑month outcomes, must‑have skills, and red flags — before you start interviewing. Without one, you're hiring on gut feel — and gut feel is wrong more often than it's right.
Role Mission (1 sentence):
"This person's job is to [do what specific thing] so that [what outcome is unlocked]."
12‑Month Outcomes (3‑5 measurable results):
Must‑Have Skills (non‑negotiable):
Red Flags (automatic disqualifiers):
Step 04 // Interview
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. Give them your actual data and watch them work. This is your single highest‑value signal.
Stage 3: Deep References (multiple calls). 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. Be vulnerable upfront: "These are the things I don't have expertise in — I'm hiring someone I can trust to lead them."
Step 05 // Questions
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?"
For a VP of Sales: "Walk me through your first 90 days — how would you assess, prioritise, and build a repeatable motion?" — "What will my revenues look like 120 days after I hire you?"
For both: "Tell me about a time you had to turn around an underperforming team — how did you diagnose and fix it?"
Step 06 // Compensation
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 (covers their cost of living), equity (vests over 4 years with a 1‑year cliff), and performance milestones mapped to compensation triggers.
Step 07 // Onboarding
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.
If you hire the wrong executive first, you'll waste 18 months and demoralise your team. Here's how to know which one you actually need.
| Your Biggest Problem | Hire This | Why |
|---|---|---|
| Operations are chaotic | COO | You need someone to turn strategy into execution — build systems, manage teams, own the numbers |
| You're the only one closing deals | VP of Sales | You have product‑market fit but can't scale revenue beyond founder‑led sales |
| Both are broken | COO first | A COO can oversee sales operations while you focus on closing; a VP of Sales can't fix ops |
When you're the bottleneck — you're spending more time managing than doing high‑leverage work, your calendar is full of meetings you shouldn't be in, and you have 12+ months of runway to support the hire. Most founders hire too late, not too early. The right time is when you can't grow any faster without handing off a major function.
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.
For a first COO at a $1M–$10M business, base salary typically ranges from $140k–$220k depending on stage, with equity of 1–2%. For a VP of Sales, base is $140k–$180k at Seed stage, $180k–$220k at Series B/C, with 0.25–0.5% equity. The right structure balances cash to cover their needs and equity to align their incentives with long‑term growth.
Hiring too early for a role they don't understand well enough to manage, or hiring a VP from a large enterprise to build a sales process from scratch. The other killer: not using a scorecard and falling for a polished interview instead of testing real operational ability.
Use a multi‑step process: (1) Screen – track record and motivation, (2) Working session – a real problem from your business, (3) Deep references – not a formality, the deepest signal you get, (4) Founder round – chemistry and delegation‑trust. Score each candidate 1–5 on a rubric at every stage.
If your biggest problem is operations — delivery, systems, team management, execution — hire a COO. If your biggest problem is revenue — you have product‑market fit but can't scale sales beyond founder‑led deals — hire a VP of Sales. 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.
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