When should I hire a second in command?
Short answer
When you have something the business needs to grow into and you can't get there because you're stuck running it day to day.
Not just a manager
A real number two takes a chunk of the business off your plate so you can do owner work. Not a glorified scheduler. Pay accordingly and give real authority or they'll quit in a year.
Pay and authority
Top quartile of market. Decision rights up to a real dollar limit. A seat at the planning conversation. Without all three, they're not a number two, they're a babysitter for the owner.
Ask your version of this question
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Now run it against your numbers.
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