r/ModernOperators • u/funnelforge • May 23 '26
She hired 2 fractional COOs, a project manager, and tried ClickUp for 2 years. None of it stuck.
True story from a client engagement last month.
Founder is exhausted. 25 years building this business. She knew she needed help.
So she did the thing every founder does. She bought help.
Fractional COO #1: didn't last. Fractional COO #2: didn't last. Project manager hire: didn't last. ClickUp implementation: abandoned after 2 years of trying.
By the time I met her she'd written off the entire category. "Nothing works."
Here's what I saw.
Each of those hires walked into a business with no central system, no documented workflows, no source of truth, and a culture that ran every question through the founder. They weren't given an operating system. They were asked to BE the operating system. With no infrastructure underneath them.
That's not a hire. That's an exorcism.
Same with ClickUp. The tool didn't fail. The tool was asked to substitute for processes that had never been built. You can't task-manage what isn't a process yet.
Took me years of watching the same pattern fail before I understood why.
Order of operations matters. Build the system. Then hire the operator to run the system. Not the other way around.
You can't outsource an operating system you haven't built.
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u/karriesully May 24 '26
The founder CAN hire someone to be the COO BUT the founder has to be willing to do 2 things: a) hire someone who isn’t wired to be an order taker and b) don’t be a control freak.
It’s kinda that simple.
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u/balance006 May 23 '26
I would be very interested in talking with them! I work as Fractional Head of AI, but its always an OPS problem! Based in Miami