Working Hypotheses

A COO's Unnamed Work Type #4: Janitor

April 2026

The last category of unnamed work was the most fun to name. I’ve heard it called “cleaner upper,” “babysitter,” “caretaker,” and “fixer,” but I think the best name is “janitor.”

Being a janitor means taking over a function for a discrete period of time, restructuring it, and then landing it in another part of the company. It starts with an ask that sounds like this example from my interviews: my CEO said to me “All we know is this broken. Marketing is not performing. Can you just go… figure it out?”11 The next sentence was: “I have played that role many times.”

There’s many reasons why a company might need this. A function could be in disarray, leaderless, underperforming, or the remit needs to be adjusted.22 Note that none of these are “a net new function needs to be built.” Although COOs do that, so do all leaders as their teams and companies grow. So I don’t view that as part of being a janitor specifically or as a part of unnamed work. Or the the org chart might be wrong, or wrong for that startup at that moment.

broom

To do this well, the COO needs an ability to get up to speed quickly, comfort flexing from macro to micro, ability to develop rapport and trust with a new team quickly, judgment, and lack of ego. The last one is particularly important. Otherwise it would be tempting not to place this team back in another part of the org.

The spark for this essay was a conversation with a COO in healthcare. This person is a delivery and G&A type of COO, so her ultimate KPI to the company was cost.33 For example, although CS teams are often considered in cost, at one point in this company the customer success org switched priorities and started to focus on revenue generation. At that time, this COO gave that team away. The big surprise is that for awhile, this COO led all of engineering.

She called it being that team’s “caretaker.” At the time, the main goals of the engineering team overlapped highly with her operations teams. They were shipping products to reduce cost and improve operational efficiency. There was some org and leader change, so she took it over until they found a new technical leader, then landed it back in its rightful place.

Another COO described the work as care without bias:

The way that the product and engineering teams were working was really, really poor... Now you had this thing that could become very political, and to fix it, you need somebody who is completely unbiased. You need to be neutral. You need to only care about the company.

Founders do this type of thing frequently. It’s even a way people describe “founder mode” now.44 This is not my interpretation of the original essay, but it is how I hear the term used a lot now.

It’s less commonly known how often COOs are running part of the company that doesn’t make any sense from the outside. That’s the point. A janitor works invisibly, cleaning up messes that other people make.

Invisibility is what defines all four types of unnamed work. They’re also temporary, inscrutable, and a bigger part of the role than you might guess.

thanks for reading
  1. The next sentence was: “I have played that role many times.” ↩︎
  2. Note that none of these are “a net new function needs to be built.” Although COOs do that, so do all leaders as their teams and companies grow. So I don’t view that as part of being a janitor specifically or as a part of unnamed work. ↩︎
  3. For example, although CS teams are often considered in cost, at one point in this company the customer success org switched priorities and started to focus on revenue generation. At that time, this COO gave that team away. ↩︎
  4. This is not my interpretation of the original essay, but it is how I hear the term used a lot now. ↩︎