When and how to hire your second in command as a founder

Executive overview

Founders who hire someone with a C-level title before that person can operate autonomously create a mis-hire. The role someone fills — director, VP, or COO — should be determined by how much direction they need, not by the title you want to give them.

Hire your second in command when critical growth tasks are sitting undone and you have no time to develop people or think strategically. Start smaller than you think: an executive assistant first, then an ops manager or director, often fractional.

Don't put a big title on a small role — design the role first, then name it.

How to tell which role you actually need

• If you're telling them what to do: director or ops manager
• If you're deciding together: VP level
• If they're showing you what needs to get done: C-level
• A true COO brings strategic autonomy — no hand-holding, and ideally brings their own team

When to make the hire

• You can't find time to develop people or work on the business
• Critical scaling tasks sit on your calendar indefinitely
• You have no time for yourself, your relationships, or the original reasons you started the company

How to hire well

• Hire an executive assistant first — fractional or full-time — to clear admin from your plate
• Design the role and responsibilities before attaching a title or compensation
• The role may only be 20 hours per week — that's fine
• Set the comp range, then fit the title to it — not the other way around
• Virtual or fractional hires are fully viable; in-person presence is rarely necessary