What I Hate About Being a Fractional CMO (And Why It's Still the Best Job I've Ever Had)

Let me say this up front so there's no confusion. Being a fractional CMO is the best job I've ever had.

I retired from academia in 2020 after more than two decades as a marketing professor, and that career was deeply rewarding. I published books, published articles, ran a foundation, trained and consulted with CEOs of companies I genuinely admired, and spent my days thinking about marketing as a discipline. It was a wonderful chapter.

But fractional work is different. As a fractional CMO, I actually get to do the thing. I solve real problems for real companies. I watch growth happen in real time. I sit in the room when the strategy I built six months ago turns into the revenue line that lets a founder hire their next ten people. There is nothing like it.

So everything I'm about to complain about, I'm complaining about lovingly. These are the splinters in the otherwise perfect job. If you're a founder considering hiring a fractional CMO, or another consultant who wants to nod along, this one is for you.

The Small Stuff (That Isn't Really About Me)

Let's start with the calendar thing.

When you bring on a fractional CMO, you usually share calendars. That makes sense. You want visibility into the work, and we want visibility into your meetings, your team's standing rituals, and your availability so we can plug in. The problem is that clients sometimes look at the white space on my calendar inside their workspace and assume that white space means I'm free.

I'm not.

I have eight other calendars layered underneath the one you can see. I have a public Calendly link on my consulting website and on Upwork, where I hold Top 1% talent status, and prospective clients anywhere in the world can book themselves into one of those slots at any moment. So when you see Tuesday at 2pm looking wide open in your view, what you're actually seeing is a slice of one calendar out of nine, not my actual life. The right move is to ask. The wrong move is to drop a meeting onto my calendar and assume I'll honor it because the slot looked empty.

This sounds petty. It's not. The reason it's not is that respecting a fractional's calendar is the single biggest predictor I've found of whether the engagement will work. Clients who treat my time like a shared resource that needs negotiation tend to get great work. Clients who treat my time like an unlimited buffet tend to get frustrated when I have to start declining things, and we end up renegotiating the relationship six weeks in.

Email is similar. I cannot answer an email the moment it arrives. If I'm on an hourly arrangement with you, every email I read and respond to is billable time, and most clients don't actually want me billing for thirty seven email replies a day. If I'm on a retainer, those emails are pulling me out of the deep work you hired me to do. The right rhythm is batched communication, and I'll always set that up at kickoff. But if you Slack me, then email me, then text me, then call me, all in the span of an hour, and then get frustrated that I haven't responded to all four channels by lunch, that's a structural problem we need to solve, not a responsiveness problem.

A few more small ones I'll list quickly because they pile up.

Tool sprawl. I'm in your Slack, your Asana, your Notion, your HubSpot, your Looker, your Figma, your Front, and your second Slack because you have two workspaces. Multiply that by every client. Resetting my password on a Tuesday morning is a sport.

The "quick question" that isn't. A quick question is "what's our domain registrar." A quick question is not "should we kill the influencer program." Both are valuable questions. They are not the same question.

Being looped into internal politics that aren't my lane. I'm here to fix the marketing. I am not here to mediate between your VP of Sales and your COO about who owns lifecycle. I'll have an opinion if you ask, but I'd rather not be the courier.

Being asked to be in every meeting. If I'm in every meeting, I'm not doing any of the work the meetings are about. Pick the four where I add the most value, and trust me to read the notes from the rest.

The Bigger Stuff (Which Is Where the Real Job Lives)

Okay. Now to the things that actually matter.

I work primarily with premium DTC brands, complex B2B services firms, and healthcare and telehealth companies. The clients I serve typically sit somewhere between $50 million and $500 million in revenue, sometimes pushing past that. My job in most of these engagements is to come in, diagnose what's actually happening, fix the marketing function, and get the company ready for whatever comes next. That next thing is usually a bigger funding round, a full time CMO hire, an acquisition, or a strategic exit.

The single hardest thing about that work is explaining to founders that you have to spend money to grow, and that the spending has to come before the growing.

This sounds obvious in a room full of marketers. It is not obvious to a lot of founders, especially founders who built their company through bootstrapped operational excellence and are now looking at marketing as a cost center rather than a growth engine. They want a 4x return on ad spend in month one with a budget of $20,000 in a category where the realistic CAC is $180. The math doesn't work. No amount of clever copy or sharp creative makes the math work. You either fund the test properly, or you don't run the test. "Let's just try a smaller version of it" is the most expensive decision a small team can make, because you spend the money and learn nothing.

The job, then, becomes translation. I have to take twenty years of marketing literature, plus a portfolio of practitioner work across DTC, healthcare, telehealth, and B2B services, and turn it into a conversation about why a $35,000 quarterly test budget is the floor, not the ceiling, for what we're trying to learn. Some founders hear it. Some don't. The ones who don't usually figure it out three quarters later, after they've spent the same money chasing four undercapitalized initiatives instead of one properly capitalized one. I am always rooting for them to figure it out faster.

The other big one, and I want to say this carefully because I love the founders I work with, is that smaller companies often have less experienced marketing personnel on the team, and a meaningful share of my engagement ends up being coaching rather than strategy or execution.

Most business owners are wonderful about this. They genuinely appreciate someone teaching their team how to read a media plan, how to think about attribution, how to brief an agency, how to interpret a creative test. I get long thank you notes about it. I love that part of the job. I really do.

What's harder is when someone on the team, often someone who has been doing marketing for two or three years, holds a strong point of view that isn't supported by the data or the literature, and I have to figure out how to gently move that point of view without bruising the relationship. People believe they know what they know. Sometimes they're right. Sometimes they're applying a tactic they read about in a newsletter that worked for a B2B SaaS company at a $5 million ARR run rate to a premium DTC brand doing $80 million in revenue. The tactics don't transfer. Neither do the assumptions underneath them.

Coaching through that, week after week, is a real part of the work. It's not in any of my engagement letters. But it's where a lot of the value gets created.

A few more big ones, briefly.

Sometimes the marketing isn't actually the problem. Sometimes the problem is the product, the pricing, the unit economics, the positioning, or the fact that the company is trying to compete in a category where the top three players have ten times the budget. Diplomatically pointing that out is part of the gig. Founders who hear it tend to win. Founders who don't tend to keep paying consultants to fix the symptom.

Clients sometimes confuse activity with progress. Five new campaigns is not five times the result. Posting daily on TikTok is not a strategy. The strategy is the thing underneath the activity, and the activity without the strategy is just exhaustion in a brand voice.

The timeline conversation. A real brand repositioning, a real channel shift, a real audience expansion, these things take six to eighteen months to show up cleanly in the revenue line. I will tell you that on day one. I will tell you that in week six. I will tell you that in month four when you ask why the new ad creative doesn't have an immediate halo on revenue. The patience required to let strategy compound is the single most valuable thing a founder can bring to a fractional CMO engagement.

The "we tried that already" reflex. You tried it for six weeks with the wrong audience and a $4,000 budget. That's not a tested hypothesis. That's a rumor.

Why I'd Do It Again Tomorrow

Every single thing I just complained about is also the reason this job is the best job I've ever had.

The calendar problem exists because I'm in demand. The email problem exists because I'm being trusted with too much, which is a wonderful problem to have. The coaching problem exists because I get to actually shape how marketing teams think, not hand them a deck and walk away. The budget conversations are hard because I'm working with founders who are about to do something significant with the right partner.

I spent twenty years writing about marketing strategy from inside academia. I now spend my days doing it, alongside operators and founders who are betting their company on getting it right. The friction in the work is the work. Everything I just listed is something I get to think about every day instead of something I read about in a journal.

If you're a founder of a premium DTC brand, a healthcare or telehealth company, or a B2B services firm in the $50 million to $500 million revenue range, and you're considering bringing in a fractional CMO, here's my honest take. The right partner will frustrate you sometimes. They will tell you no. They will tell you the budget is too small. They will tell you the timeline is too short. They will coach your team in ways that occasionally feel like extra labor on your end.

That friction is the job. The friction is what you're paying for.

Most engagements are NDA'd, but what clients consistently tell me is that the hardest conversations were the ones that ended up making them the most money. That tracks with my experience too.

If that sounds like the kind of partnership you want, my Calendly is on the site. The slot might already be booked by the time you click. That's actually a good sign.