Office Hours, August 27th: 12 Interesting Questions About Fractional Work, Answered by Taylor Crane

I hosted my third Office Hours on August 27th. Lots of first timers, a handful of people who have now been to all three, and about 90 minutes of questions.

Here are all 12 questions from the session with my answers. A few are about finding the work, a few are about doing the work, and a few are about what I'm seeing from the companies making these hires.

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Are VCs actually a good channel for finding fractional clients?

Jennifer asked this. She's exploring fractional marketing and product marketing work in Austin after a few months of full-time job searching, and heard VCs were a way in.

My answer is an emphatic yes and an emphatic no at the same time. The yes: if you can build a real relationship with a VC firm that has a portfolio and has that portfolio's attention, it can be a gold mine. I know multiple fractionals whose clients almost all come from a single firm. The way in is to offer the firm something easy to hand out, like a free one hour session on GTM or product marketing for any portfolio founder. That makes the intro effortless for the VC, and it becomes your lead in to a client.

The no: most VC firms are useless in this capacity. I've tried this route myself for Fractional Jobs. Investors do one thing exceptionally well, which is write checks, and most are not equipped to do much else. A minority have platform teams or genuinely do value add work. So if you already have relationships, absolutely experiment. If you're going in cold, try it, but don't expect much. The version I'd bet on for you is showing up at an in person event hosted by a local Austin firm and building the relationship there. Cold emailing a fund to announce you're open for business is not going to make portfolio companies start appearing.

For more reading on this, check out How to Get Your First Fractional Clients.

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How much do you still have to educate companies about fractional?

Courtney asked this. She's been fractional for three years and wanted the view from someone talking to a much larger volume of hirers.

Less than I used to, and that's new. I had a call yesterday with a CEO who opened with "I'm already familiar with fractional, I have a fractional CFO and a fractional general counsel." That would have been rare not long ago. Companies are also walking in already knowing what fractional costs, which is funny for me, because a lot of that compensation data is mine. Founders ask an LLM what a fractional CMO costs, it cites my content, and they show up quoting my own language back to me. It's good. It shortcuts the misconceptions.

I'll also say I'm betting this phase of my career on the fractional trend and I'm more confident than ever. I now have several clients building out entire executive teams with fractional leaders. One health tech client has hired four people from us. Another is on their third and fourth. It's not crazy to think the next few years bring waves of early stage companies built with entirely fractional leadership. Ten or twenty years from now I think this will look obvious, and the question will be why it took so long to normalize.

For more reading on this, check out Why is Fractional Work Growing So Quickly in Popularity?.

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Is there a fractional market for leadership and organizational transformation work?

Asma asked this. She's been doing fractional CMO work since 2015 and wants to move toward executive team transformation and facilitation, but never sees roles like that posted.

Here's the distinction I'd draw. Fractional work, in its simplest form, is a company that wants a CMO but doesn't have the need or the budget for a full-time one, so they hire a fractional CMO instead. You come in, you run the function, you just do it part time. What you're describing sounds more like coming in, doing the work, and getting out. That's a fixed project, and it's closer to consulting than to fractional. I wouldn't expect to post a standalone fractional organizational transformation role on the site.

What I do see, and can see more of, is "we want a fractional CMO who can transform the marketing organization." The transformation is part of the job, not the job title. So my honest advice is to use the CMO work you already win as the way in, look for the transformation opportunities inside those engagements, get reps and case studies, and take that offering to market over time. I'm sure the demand exists. I just can't tell you from my vantage point where it's coming from or how it's being bought, and that's where my expertise ends.

For more reading on this, check out The Difference Between Fractional Work, Freelancing, Consulting, and Agencies.

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What's the biggest mistake people make early in their fractional career?

Luis asked this. He does performance marketing and signed his first client the week of the session.

Not asking your clients for feedback. When I was doing fractional product work, about halfway through that year I had a client I couldn't read. I felt like the work was good, but I wasn't confident about it. I asked a friend who'd done a lot of fractional work whether I should ask the client how I was doing, and he said absolutely not, you're the expert, you tell them what to do. I sat with that for a couple of weeks and it didn't fit me. My background is product, where you put half baked work in front of users and let them tear it apart.

So I sent the client an email asking how they were feeling and where I could be doing better. The response changed the relationship. He told me the work was great, but that he couldn't tell whether I was giving him the honest truth or telling him what he wanted to hear. He was right. I'd been softer than I should have been. After that I came in saying what I actually thought was wrong and what I actually thought we should do, and it opened the door to a much more honest partnership.

The broader version of this mistake: if you've come from agency or client services, you already have an intuition for managing client relationships. If you spent your whole career as a full-time employee at product companies, you have more reps to get in on the difference between working for a boss and working with a client.

For more reading on this, check out How a Fractional Job Works, in Practice.

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Should a fractional CFO position for early stage companies, or wait for growth stage?

Frederick asked this. He runs a fractional CFO practice targeting early stage startups and noticed the Fractional Work Report shows finance only becomes the number one first hire at growth stage.

It can be good positioning, but it will require you to focus on specific niches within early stage. The pattern in the data and in my conversations is real: CFOs, general counsels and CISOs are in more demand later, because those are problems that show up later. At the earliest stages, the only things most companies care about are product and distribution. Strategic finance work, which is what a CFO does best as opposed to a controller or bookkeeper, tends to become urgent when the rounds get bigger and the data room gets serious.

But early stage is not out of the question, it just depends on the company. Yesterday we posted a fractional CFO role for a pre market medical device startup at pre seed. The CEO is a physician raising a big round who wants a real business partner to help him think through how much money they need, where it goes, and how to craft the investor pitch. He wanted someone with medtech and medical device fundraising experience specifically. Those are the kinds of companies to go find. The other option is to build a graduation path into your practice: start light touch on the controller side, then step into the strategic CFO seat when the company needs it. And at the earliest stages, a blended CFO/COO business partner could be a genuinely differentiated offer.

For more reading on this, check out Hiring a Fractional CFO.

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New leadership roles keep getting invented and I hear about them a month too late. How do I catch them?

Craig asked this. He spent 25 years in tech at companies like Cisco, Salesforce, ServiceNow and SAP, and keeps hearing from contacts that he would have been perfect for a role that's already filled.

Chances are those roles aren't being posted anywhere at all. Most fractional work still gets done through private conversations and networks. I'm doing my best to change that with Fractional Jobs, but that's how the industry works today. Which means the fix isn't finding a better place to look. It's making sure the people who already know you think of you at the moment the need comes up.

That's what LinkedIn is actually for. Most advice treats posting as a way to reach strangers who become inbound leads. That happens, but it's the hard version. The much lower hanging fruit is reminding your existing network what you do, over and over, so that when they're in a meeting where a GTM need comes up, you're top of mind because they saw your post yesterday. Not because they bumped into you at a happy hour a year ago.

Craig's honest pushback was that LinkedIn is full of people claiming expertise they don't have, and it's exhausting to compete with. I agree, LinkedIn is in a lot of ways a dumpster fire. You can either get over that or decide it isn't for you and find other ways. What I'll say is it objectively produces results if you do it right, and one thing I see working well is people who know LinkedIn is a mess and lean into it. Be your actual self with the people who already know your personality. That plays much better than another "excited to announce" post.

For more reading on this, check out Why Don't I See any Fractional Roles for Me or My Function Area?.

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Why do so many fractional job descriptions read like recycled full-time ones?

Corey asked this. He's in sales leadership and kept noticing fractional postings that look like a full-time JD with the word fractional dropped on top.

Because that's exactly what they are, and it makes no sense. I see a ton of it. Companies used to hiring full time go through the same motions without thinking about what's different about hiring fractional. I've seen fractional job descriptions with benefits and healthcare language for W2 employees still sitting at the bottom. I honestly don't know what they're doing.

Worth knowing how this works on my site, though, because we have two kinds of jobs. Syndicated jobs come from crawling about 175 sources to pull in every fractional leadership role we can find, so the newsletter is a one stop shop. For those, I'm usually not talking to the company at all, and we're at the mercy of the JD they wrote. Featured jobs are clients who came to me directly. I write every one of those job descriptions myself, after talking through expectations, compensation and the ideal candidate. You'll never see W2 language in those, and you can hold me to it.

For more reading on this, check out The Difference Between Featured vs. Syndicated Jobs on the Fractional Jobs Website.

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Is sales the last function companies are willing to hire fractionally?

Corey also asked this. His read was that fractional CFOs and CMOs have been normal for years while people still scratch their heads at the idea of a fractional sales leader.

You're not wrong that sales is behind CFO and CMO, but I don't think it's at the absolute bottom. I'd put it in the middle. There are real reasons for it, and the head scratching you're describing is one of them.

Here's the part I'd pay attention to though. If I had to bet on the fastest growing fractional role right now, sales is probably at the top of that list. Not the most popular, still growing the fastest.

For more reading on this, check out What Are the Most Common, and Least Common, Fractional Roles?.

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I do all the networking I can, then reach out cold to companies I want to work with and hear nothing. What am I doing wrong?

Barry asked this. He finds an organization he'd love to work with, figures out who the CEO or CFO is, sends them information, and gets nowhere.

Probably nothing. When you reach out to someone cold, the odds of getting any response are under 5%, and the odds of a positive one are more like 3%. If you ran a 6% positive reply rate you'd be crushing it, and that still means 94% of the time you hear nothing at all. Your experience is the norm.

That's why I put cold outreach in the advanced bucket. It needs a system and some scale to work. Reaching out to one CEO a week isn't outreach, it's a lottery ticket. You'd need to be sending something more like 10, 50, maybe 100 plus a month before it produces value. It's also why 80 to 90% of your clients today are going to come from warm connections and referrals. Marketing is hard, sales is hard, and outbound is the hardest version of both.

For more reading on this, check out How to Get Your First Fractional Clients.

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I only work with clients I can be on site with. Is that limiting me too much?

Corey asked this one too. He sticks to the tri state area because he believes sales leadership needs face time, and wondered whether he's leaving too much on the table.

You're doing the right thing so long as you have clients. If the pipeline is running dry, then it's worth questioning. It also depends on the kind of sales work you do. With B2B SaaS, being in the office is nice to have and not much more.

But I work with plenty of companies where it's a real value prop. More location based brands, more legacy businesses, founders who are traditional in that way and want someone nearby. The fact that you'll drive to Connecticut or Pennsylvania to spend face time is something those founders will pay for. It's a double edged sword. The thing that differentiates you is the same thing that shrinks your pool.

For more reading on this, check out What Does a Fractional Job Typically Look Like?.

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I narrowed my offering down to two areas. Is two still one too many?

Holly asked this. She's a generalist who came out of the last Office Hours and cut her positioning down to fractional operations consulting and client account management.

The traditional answer is that specialization wins, and the reason is the buyer's shoes. If you need a cleaner for your wood table and you're looking at two bottles, one says wood cleaner and the other says wood and glass, you're picking up the wood one. That second bottle is better if you also have glass. But when you only have wood, the specialist wins. Same thing with your two listings.

That said, I don't think LinkedIn is your bottleneck. You're looking for one client at five to ten hours a week, and that client is almost certainly coming from your network. So keep both on LinkedIn, see what happens, and put your energy into conversations with peers and former colleagues who already know your work. Which offering resonates will become obvious from the leads that come back. If no leads are coming back at all, that's the signal that you need to push harder on the network, not that you picked the wrong one of the two. Forcing yourself to choose now and re-optimizing everything around it is the worse move.

For more reading on this, check out How to Position Yourself to Attract Fractional Work.

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How does Fractional Jobs itself get in front of companies?

Holly asked this one too. She wanted to know where the demand side actually comes from.

A lot of it came from my network when I first started the business, which I realize is the same answer I've been giving all session. But the biggest channel today is LLM search and SEO. We don't do paid media. Fractional Jobs has become authoritative enough in this space that when a founder asks an LLM how to find a fractional CMO, we come back as one of the top recommendations. That's where a lot of our clients come from now, plus a hodgepodge of other stuff.

For more reading on this, check out What is Fractional Jobs? (The site you're reading this on!).

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That's a Wrap!

Three Office Hours in and these keep being the most energizing thing on my calendar. It was a dreary morning in New York and I logged off feeling great.

Coming up: we released the Fractional Work Report 2026 a few weeks ago, all 88 pages of it. It was written for industry thought leaders, so a much more digestible piece built around the community survey results is coming in the next couple of weeks, along with a dedicated session where we dig into the report itself. Watch the newsletter for that one.

The whole Office Hours series is presented in partnership with Collective.com, and I'm super grateful for them. If you're at the point in your fractional practice where you need to set up your LLC or S Corp and start taking your business more seriously, you should learn about how Collective can help.