I’m a fractional COO who spends a lotttttt of time inside early-stage companies figuring out why smart people are working very hard and everything still feels harder than it should.
Usually the founder is still answering half the questions.
Sales thinks Customer Success knows something they absolutely do not know.
There are six tools involved in a process that could probably use two.
Someone made a beautiful Notion page six months ago, and no one has looked at it since.
You know. Startups.
Systems & Side Eyes is where I write about all of that.
What you’ll find here
I write mostly for founders and operators building growing companies, especially the ones somewhere between “we figured out how to sell this thing” and “oh God, now we have to build an actual company.”
You’ll see stories from inside startup operations, thoughts about founder bottlenecks, team communication, onboarding, ownership, meetings, AI, leadership, and the occasional bit of startup anthropology.
My general operating philosophy is pretty simple:
Chaos is a stage. It is not a strategy.
A founder shouldn’t have to permanently function as the company’s operating system.
Good operations should make a company feel calmer, not more bureaucratic.
And most teams do not need another 47-step framework. They need somebody to figure out where the confusion actually starts.
A few good places to start
If you’re new here, these are probably the best introduction to what I write:
The very real version of leaving traditional employment and building a portfolio career.
I accidentally talked about how I get clients
A behind-the-scenes look at how my own business actually grows. Including the parts I would prefer to pretend are highly strategic.
The Systems Person Forgot to Build One for Herself
Exactly what it sounds like. (I know. I know.)
OMG I Just Realized I am the Dr. Robby of Startups
One of my favorite examples of what happens when the human side and systems side of work collide.
If your company feels a little too dependent on you
That is the work I do outside this newsletter.
I work with growing B2B SaaS founders as a Fractional COO and Operating Advisor. Usually I’m brought in when the company is working, but the founder is still holding too much of the context, ownership is getting fuzzy, or the handoffs between teams are starting to hurt.
Sometimes that means an embedded partnership.
Sometimes you just need another experienced operator in the room for one messy problem.
Operator Office Hours
Bring me the thing you keep turning over in your head.
A team problem. A handoff that keeps breaking. A role you can’t figure out. A process that somehow has 14 steps now. Whatever.
We spend 60 minutes on it.
You leave with a clear recommendation and a written outline of what I would do next.
$250 for 60 minutes.
The Operator’s Backroom
Paid subscribers also get the Operator’s Backroom, where I go deeper into the systems I actually use and the problems I see repeatedly inside growing companies.
Less “thought leadership.”
More “here is how I would actually fix this.”
And that’s pretty much the deal.
If you’re building something and occasionally wondering whether everyone else received the secret manual for running a company...
They did not.
Welcome.
Katie