People
8 min read
Hiring your first head of operations
The founder who has done everything is the hardest person to replace. Here is how to hire your first head of operations, and how to let go.
Tomas Hale
Partner, operations

At some size, the founder becomes the bottleneck in a business they built. The answer is a head of operations, and the hire fails more often than it works.
Write the job as three outcomes
Do not list tasks. Say what will be true in a year: orders leave on time, the month closes in five days, and you take a fortnight off.
Hire for the gap, not for a copy of you
You are good at starting things. Look for someone who is good at making them repeat.
Let go on a schedule
Agree in writing which decisions move to them by which month. Founders who leave this vague take the decisions back.
The Aldermere Letter
One essay a month, short enough to read on the train.
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People
Hiring your first head of operations
The founder who has done everything is the hardest person to replace. Here is how to hire your first head of operations, and how to let go.
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