One of the questions I get most often from people considering fractional work is what my days actually look like. I always struggle a little with the answer because there is absolutely no normal day, and the job description changes depending on which company I’m working with and what is currently on fire.
I might spend the morning rebuilding an entire customer onboarding journey, figuring out where Sales is handing off incomplete information, where customers are getting stuck, and what needs to change to make the experience better. Thennn an hour later, I’m helping a finance team figure out how to name and organize their documents so leadership can actually find the financial information they need.
Both of those things are operations. Both are important. One sounds considerably more impressive when I tell people what I do for a living. I’d say that’s probably a pretty good introduction to fractional COO life.
You get invited into someone else’s mess
When I start working with a founder, they usually have a pretty good idea of what they think is wrong with their company. They’ve been living with the problems, feeling the friction, and probably personally compensating for a lot of it.
I listen. I empathize. I try not to immediately assume they’re right.
Not because founders don’t understand their businesses, but because the view from the founder’s seat is only one view. The really interesting stuff tends to surface after I’ve talked with the people doing the work or been unleashed on the company Slack.
That’s when I start finding the gaps between what leadership thinks is happening and what is for real happening.
Sometimes a founder thinks they have a performance problem, but the team has never been given clear ownership. Sometimes everyone is frustrated with communication, but the real issue is that nobody knows where decisions get made. Sometimes a process looks perfectly reasonable on paper until you talk to the three people who have developed entirely different ways of working around it.
I weirdly love this part. It’s a little like being a detective, except the mystery is why five very smart people are having the same conversation every Tuesday.
The nice thing about having spent more than 15 years inside startups is that very few of these situations are completely new to me. The people and products are different, but the patterns start to look familiar. I can usually get to something useful much faster than someone who has to learn every lesson from scratch.
That speed is a MASSIVE part of what founders are actually buying.
Sometimes I’m working on things I never expected to touch
My background leans heavily toward the commercial side of businesses. I’ve spent a lot of time in marketing, communications, revenue operations, customer experience and the messy places where those functions meet.
Yet one of my health tech clients needed help establishing better rhythms and communication cadences for an engineering team.
Engineering! Not exactly where I expected my marketing and communications background to take me.
Except the underlying challenge wasn’t really about engineering. It was about how people communicate, make decisions, surface blockers and coordinate work across functions. Those problems show up everywhere, even when the technical work itself is completely different.
I didn’t need to become an engineer. I needed to understand how that team worked, where things were getting stuck, and what structure would actually help them.
This is one of my favorite things about being a generalist operator. You learn that so much of what makes a company function well is transferable. You just have to be willing to learn enough about the people and their work to apply it thoughtfully.
Occasionally that means going from a high-level strategy conversation to reorganizing a folder structure because nobody can find the numbers.
Sadly, there is no glamorous way to explain that last part. Still matters though!
The relationship can feel surprisingly close to having another co-founder
I think one of the biggest misconceptions about hiring a fractional COO is that you’re buying a certain number of hours of operational advice.
You can certainly structure an engagement that way, but the work I enjoy most is much more embedded.
A founder brings me into the business because they’re carrying too much of it themselves. They’re making decisions that other people should be able to make, keeping track of work that should be visible to the team, and spending time solving problems that keep coming back.
When the relationship works, I become another person who can hold some of that weight.
I can get into the details, have the uncomfortable accountability conversations, follow up on things that aren’t moving, and make decisions about what deserves attention RIGHT NOW versus what can wait. I can also tell a founder when I think they’re contributing to the very problem they’re frustrated by. Lovingly, of course. 😘
I don’t have the founder’s equity or their history with the business, and I’m not pretending those things are interchangeable. But I can bring a level of ownership and investment that feels a lot closer to an operating partner than an outside consultant.
For a founder who has been the default answer to every question for years, having another experienced person who can see the whole picture and actually do something about it can be an enormous relief.
Since I’ve been inside so many different versions of startup chaos, we don’t have to spend six months getting to that point.
There’s also the business of being fractional
Now for the part that doesn’t make it into the dreamy posts about fractional careers.
You still have to find the clients.
And unless you happen to have an enormous network of people waiting to hire you, that is a whole job in itself.
You’re building a brand, explaining what you do, creating content, meeting people, following up, nurturing relationships, and trying to stay visible enough that someone thinks of you when they finally realize they need help.
Then you sign a client, get wonderfully busy doing the actual work you love, and suddenly remember that you’re also responsible for keeping your own pipeline alive.
It’s a fascinating little cycle. (I spoke more here about how I discovered I am a lot like my founders when it comes to running my own biz.)
The irony of being an operations person running a fractional business is that you can be extremely good at building structure and accountability for other companies while having to remind yourself to apply the same discipline to your own.
Client acquisition has been one of the hardest parts for me. Not the actual operating work, which is where I feel most at home, but continually making the case for why someone should bring me into their business. (I find it very hard to sing my own praises. In an attempt to get over this, I recently asked some clients and past co-workers to recommend me as a little exercise. Highly suggest you do this as well!)
Then there’s also the emotional investment.
I care about my clients. I care about their teams, their customers, their goals, and whether the things we’re building actually work. I’m still learning how to care deeply about a business without carrying every one of its problems home with me.
Being fractional doesn’t automatically make you emotionally detached. Sometimes it just means you have several companies to worry about instead of one.
This my friend is a very efficient way to diversify your anxiety.
The people might be my favorite part
For all the challenges, one of the biggest surprises has been how much I enjoy the people I get to meet.
I get to work with founders who have built things I never would have thought to build, teams solving problems in industries I might otherwise never have encountered, and incredibly talented people with completely different areas of expertise.
I get to learn how other people think. I get to see how different businesses operate from the inside. And I get to bring something I’ve learned in one environment into another where it might make a real difference.
That last part is especially satisfying.
Every company feels unique when you’re inside it. And of course, in many ways, it is, but after enough time moving between them, you start to realize how many challenges are shared. A founder struggling to delegate, a team with unclear ownership, a customer journey full of unnecessary friction. The details change, but the underlying problems often rhyme.
I think that’s what makes fractional work such a good fit for the way my brain operates. I like variety, I like figuring things out, and I like being useful. I especially like the moment when something that has felt impossibly complicated to a team suddenly becomes manageable.
I don’t need to be the permanent person in the room to help create that change.
So what does a fractional COO actually do?
Some days I help founders think through the next stage of their business. Some days I hold teams accountable to decisions they’ve already made. Some days I build the systems that allow people to do their jobs without constantly asking for permission.
And some days I organize financial documents.
The through line is that I help a company work better, whatever that happens to require.
For anyone considering a fractional career, I’d say the freedom and variety are real, but so are the responsibilities of building a business around your expertise. You have to be good at the work and willing to keep putting yourself out there so people know that work exists.
For the founders wondering what it would feel like to bring someone like me into their company, I think the biggest difference is that you don’t have to figure out every operational problem alone before asking for help.
You can invite someone into the mess while it’s still messy.
In fact, that’s generally where I do my best work.
Just please don’t make me guess which spreadsheet is the real one. 🤪
Want to get into the weeds together?
Whether you’re a founder trying to figure out what to hand off, an operator navigating a particularly messy challenge, or someone exploring a fractional career of your own, I offer paid Office Hours for exactly these kinds of conversations.
Bring me one thing you’re trying to untangle. We’ll spend 60 minutes working through it together, and you’ll leave with a clear, actionable plan for what I’d do next.
I think I just decided what I want to be when I grow up! You sound phenomenal ✨️