Fractional C-level Roles with Matthew Fenton

SEASON 8, EPISODE 6

If you've been on LinkedIn lately, you may have noticed bios that include a “fractional” C-level job. Traditional C-suite jobs can be all-consuming, require deep expertise, leadership and ownership, to a certain extent. For many freelancers, we probably don’t imagine holding a C-suite position, besides being the CEO of our own businesses. 

So — what’s the hype over these fractional C-level positions? 

In this episode, Wudan talks with Matthew Fenton. 

Matthew is the founder of Three Deuce Branding, a consultancy with a simple mission: to help good people build great brands. Since 1997, his company has helped hundreds of clients — including Fidelity Investments, Wrigley, and Valvoline — to achieve "brand clarity" by better positioning, strategy, and messaging. Matthew has spent seven years in brand management.  For a year and a half, he's worked as a fractional CMO/CSO for Bob Rogers Travel. He's also the founder of the coaching business Winning Solo. 

Wudan and Matthew dive into the benefits of fractional roles, how to determine if a fractional role is right for you and what you can do to work your way up into a fractional position.

Full Transcript Below:

Wudan Yan- Hi, everyone. Welcome back to The Writers Co-op. I am your host and executive producer, Wudan Yan. Welcome back to Episode 6 in Season 8: The Year of Expansive Thinking. Today on the show, we are going to talk about a title that I've been seeing come up a lot on LinkedIn: fractional C-level positions. It's gotten me pretty curious, to say the least. My spouse is a company founder, so I'm very well-aware that in startups, there's a CEO, which is the Chief Executive Officer, if you're working in tech, there's a CTO, which is the Chief Technology Officer, COO is Chief Operating Officer, and so on and so forth. The corporate term for the C-level positions is CXO, where you can sub in the X for another letter, that tends to be a little more descriptive of what someone's job is. And usually all of those C-level jobs are full-time jobs that are very committing. But I'm starting to see people describe themselves as a fractional CFO, Chief Financial Officer, and more likely also seen solopreneurs who work in marketing dub themselves fractional CMOs on LinkedIn. Needless to say, again, I have a lot of questions about how to get into a fractional CXO position, because C-level connotes a lot of things. It connotes deep expertise, leadership, ownership, and to a certain extent, potentially higher stakes overall. For many freelancers, we probably don't imagine holding a C-level position besides being the CEO of our own businesses. So what is the hype over these fractional C-level positions? Why are we seeing more of them? To talk about fractional C-level work, I brought on Matthew Fenton. Matthew Fenton is the founder of Three Deuce Branding, a consultancy with a simple mission: to help good people build great brands. Since 1997, Three Deuce has helped hundreds of clients, ranging from Fidelity Investments, Wrigley — yes, the gum—and Valvoline to acheive brand clarity via positioning, strategy and messaging. Matthew also spent seven years in brand management, including two as a CMO, Chief Marketing Officer. In that time, he developed and launched White Mystery Airheads, grew Trolli Sour Brite Crawlers into the best selling gummy worm in the country, and led brands to double digit growth every single year. So, as a side note, that Matthew worked on Trollis is probably my favorite fun fact about him, since I cannot live without Trollis when I'm out hiking or backpacking. This is not a Trolli-sponsored ad. In 2021, Matthew founded Winning Solo, a coaching business designed to help other independent consultants and creatives to enjoy longevity, balance and success on their own terms. Before we get into today's episode, did you know that we have an online community for The Writers' Co-op? If you're looking to do big things in your freelance business this year, or just crave ongoing support from a welcoming, safe, inclusive community, join The Writers' Co-op on Slack. Hundreds of members are sharing best practices and tips when it comes to running their freelance business. I can't overstate how important it is to have a psychologically-safe space to bounce ideas around and ask questions. Sign up today at the All-Access level on Patreon to get a link to join. That's at patreon.com/TWCpod. Here is my conversation with Matthew. Matthew, welcome to The Writer's Co-op. It's a pleasure to have you here today.

Matthew Fenton- Thank you, Wudan. I'm happy to be here.

Wudan- We are here. We are doing the thing. So here is my first question for all my guests, Matthew, which is: What do you do and how did you first get started on your career path?

Matthew- Okay, I'll start with the second question first. So how I got started was in effect, I made the decision in 24 hours. Going way back in time, I started my career in brand management, was actually brand manager for Airheads candy. So I am in fact the fellow who launched White Mystery Airheads. Yes, I know what the flavor is. No, I will not tell you or your audience because I don't want to get sued. But it was also the same company that did Mentos during the fresh maker campaign back in the 90s. Total blast. Wonderful people. Good time. In a moment of colossal stupidity, I left that job to take a job as a group brand manager at a Fortune 200 company, which shall nameless. I was exceptionally miserable. Couldn't get out of bed, which hasn't happened before or since. So I called the Airheads people back, said hey, made a mistake. I'm not looking to get my old job back. I am thinking about launching a consultancy. They said they had work for me for the summer, and I ended up making what turned out to be a life-changing decision in less than 24 hours. So I submitted my two weeks' notice in my eighth week at the Fortune 200 company, and importantly—important detail coming—during my 10 weeks in that job, I joined a marketing retreat, department-wide. So dozens of us, off-site. And management brought in some consultants to "teach us how to do positioning." One of the consultants said, and I'm quoting: "A rational positioning is better than an emotional positioning, because a rational positioning can be proven." And I had just left Candyland. And I was like, okay, explain the entire candy industry to me. If a rational position is better, explained Coca-Cola to me. So I was aware that I was confronted by people who maybe weren't the sharpest knives in the drawer. And they had managed to get hired by a Fortune 200 firm. So I figured if they can get hired, I could probably carve out a decent living as a consultant. That was 1997, when I was 27. And here we are 27 years later, and I'm still doing my consultancy thing.

Wudan- That's amazing. I mean, I think of the freelance talking heads on social media, and I'm not calling you a talking head, but people who give advice, and you know, I'm just totally, always so impressed by what you have to share, because it comes from this deep, deep expertise. So I'm really excited to dig into that, and this conversation about fractional work. So tell us about your consultancy business now. And what form that takes.

Matthew- Sure. What I do today is what I would call a core brand guidance. So I only do positioning, strategy and messaging. So sometimes it helps to tell a newbie what I don't do. I do not do ad copy. I am not a copywriter. I do not build websites. I do the upstream stuff. Questions one, two, and three. So I work with my clients on questions like: Where will we play? How will we win? What does winning even look like for us? What will we stand for? Who cares most about that? That's what I do all day long. I like to put the particular puzzle together. Over the years, I've earned repeat business from brands like Fidelity Investments and Wrigley and Vaseline, but I've also done work with challenger brands and regional and niche leaders, down to, you know, eight or 10-person accounting firms, all the way up to $20 billion firms. Along with that, I've done some public speaking, some workshop facilitation, some ideation. And most recently, what we're here to talk about today, is I have added the fractional CMO arrow to my quiver.

Wudan- Yes. Yes. So when you help companies with that positioning, what is the thing, title that they hire you for?

Matthew- They hire me to, again, it varies, but they're usually dealing with some kind of question about: What will we stand for? What makes us different: And who are the people that really care about that? So one example, I've had a client for 12 years, Bob Rogers travel. We'll talk about them some more today, I'm sure. But the reason they hired me in 2012 was because they were about to build a new website. And they had that sinking feeling where they're like, "Okay, I need to build this thing. But I have no idea what we should be saying. No idea who should be talking about." So they had the good sense to go upstream, instead of just jumping into website design. They called me and said, we want to work on that core problem of: Who exactly are we? What do we stand for? Who cares about that? And that started a relationship that's lasted now for 12 years.

Wudan- Wow. Yeah. So kind of brand identity consultant in some senses. Right?

Matthew- Right, right positioning and strategy, specifically. Brand identity, folks, I want to make sure I'm not stealing their thunder, because there are people who do really, really strong visual identity.

Wudan- Yes.

Matthew- I know, some truly outstanding designers. I am not one of them. That is not in my toolbox. So depending on how we're defining identity, that is or is not what I do.

Wudan- Would you say your specialty is helping people see the bigger picture?

Matthew- Absolutely.

Wudan- Yeah.

Matthew- Absolutely.

Wudan- The fractional work is what we're talking about today. And I really want to dive into that. So can you help us define what a fractional CMO, which is Chief Marketing Officer, or fractional CFO, Chief Strategy Officer, means?

Matthew- I will do my very best. It's a good question, because I don't think there's an industry-standard definition. It might be easier for me to start with what it's not, because I've heard some people say, "Oh, I'm a fractional CMO for four different companies right now. And I spend five or six hours a week on each." And that makes me think we have very different definitions of what fractional means. What that person describes sounds like, you know, good old-fashioned consultant to me, but maybe not a fractional type of role. So for me, a fractional CMO, or fractional anything, is someone who performs all or most of the function of the traditional role, but without being full-time and in-house. So that's how I think of it. You're either doing all or most of the traditional job description for the title that fractional proceeds.

Wudan- And are these job listings that the company is putting out like "We're looking for a fractional CMO?" Or do they kind of like hire you as a strategist? And as you get into that relationship, you're like, "Hey, I'm noticing what I do is typical for what a CMO would do. Can we have that conversation?" What's that like?

Matthew- That's also a really good question, because I don't think there's a massive market for, "Hey, I'm an employer, and I'm looking for a fractional type of person." It's my belief without any data behind it, that these are the kinds of things that you're going to grow your way into, typically, with a client that you already know. I think you're more likely to get that role, if they already have some experience with who you are and what you do. So in the case that I'm currently in, the client that I mentioned earlier, Bob Rogers Travel, I'll first tell you about them. They are in the business of student performance travel, which would be taking the high school band to Disney World, or to perform at Carnegie Hall, or to do a five-country tour of Europe. These are all things that Bob Rogers does. It's a very niche business. And as I said earlier, I had been working with them since 2012. Started as a one-off positioning project, then evolved into leading their strategic planning process, into guiding special projects for them. So I knew them. And they knew me. Last January, they lost their head of marketing. He resigned to take a different position. And they called me up in a bit of a panic, needing a stopgap: We need some help. We need an immediately. We don't know for how long we need it. And it's evolved into what it is today, which most weeks requires between about 20 and 25 hours of my time, with a few peaks kind of mixed in there during periods of high activity. But as I said earlier, I do think that the level of familiarity matters for a partnership like this, and I think it matters for both parties. So had it been a company coming to me cold with the exact same request that Bob Rogers Travel put in front of me, I probably would not have said yes. When Bob Rogers Travel asked—because I know them, I know that they're wonderful people and fantastic executors. I knew their business well. I knew exactly what I was getting into—in that case, it was a very quick yes, even though I was already pretty busy with other work at that time.

Wudan- And is Bob Rogers, your only fractional CXO role? Or are there others?

Matthew- They're my only one right now. And frankly, they're the only one I could handle. I think if we stick to my definition, if we accept that as true, I think it would be really, really difficult to take on a second client at this level of activity and to actually perform that job well. That would put me in a period of bandwidth overage.

Wudan- Yeah.

Matthew- So I might be able to do it for a short period of time. But I think it's really, really difficult to do more than one of these well at a single point in time.

Wudan- Well, I just think it's so interesting, listening to you talk about how other people might have four fractional roles. It sounds like they are just trying to get all those fractions to add up to one.

Matthew- That's that's quite possibly true.

Wudan- Taking the literal definition of what a fraction is.

Matthew- Right. 4 times 1/4 equals 1.

Wudan- Yes. It also seems like these roles that you've found yourself in that our fractional are a win-win for you and your client. Would you agree with that?

Matthew- Yes, very much so. And that's—I love that you're making that point, Wudan, because that cuts across, I think everything we should be striving to do as independent consultants and creatives. It really only works when both parties are feeling like they're getting a really good deal. I think those are also the conditions in which we do our best work, because both parties are seeing the value. So this is an extension of that core principle—that if it's not a win-win, something bad is gonna happen down the road.

Wudan- Right, like, they are getting your deep expertise, and you already have this relationship, but they probably don't have to pay for your benefits. And you still have the flexibility of where and how you work.

Matthew- Right. I think that's one reason it really works in this situation. And I'm sure we'll unpack the question of: What are the prerequisites to make a roll like this happen? But it does help that I've been a CMO in the past. So a part of my work history that we didn't cover is in 2010 and 2011, I joined another candy company. They were about 600 million at the time. They are now part of the Ferrera family of brands. But we had brands like Brach's, Trolli — got your Sour Bright Crawlers in there —you know, other brands like Chuckles Fruit Stripe gum, which everybody claims to love, but nobody actually buys, just kind of this legacy portfolio of brands. But I had that. I had been a CMO for two years. And so in some ways, Bob Rogers is seeing the benefit of my experience there in that I can step right into this role with no training needed, with a different point of view, having worked with a somewhat larger company, having managed large teams, having managed agencies, et cetera, et cetera. And I think that's another condition in which the fractional relationship really works well: Is when you can come in and say, okay, I can do great work, perhaps even more efficiently than somebody else, because I have this relevant history to bring to the table.

Wudan- Yes, that makes total sense. So Matthew, I'd like to hear about what a typical work week looks like for you. If say, your fractional role right now takes up to 25 hours. What other time are you spending on other endeavors in your business?

Matthew- Sure, it's a great question. I will say, historically, I'm most comfortable, around 30 to 35 hours a week in total. And that's been my, my running rate for about the last decade. With the addition of the fractional role, I'd split it out to be a number that adds to a little bit higher than that. So I'm doing 20 to 25, on the fractional CMO role with BRT. I'm doing about five to 10 hours a week with other client work. And then about another three to five hours on Winning Solo, which is my coaching business for independent consultants and creatives. So it has been a period of high bandwidth. And I think we'll also talk about, you know, kind of the benefits and the drawbacks of the role. But one of the potential drawbacks—though, it also definitely has an upside—is that the fractional role is going to lock you into a period of sustained, high activity on one client. And for some independents, that's a big negative. For others, it's a huge plus. But it's something that's worth considering, I think, for anyone who's thinking about a fractional type of role, is that it is a—it's a commitment. And if you're going to do it, well, it is not a one or two month type of commitment. It's probably got a runway of six months or more.

Wudan- And that stability can be really nice for freelancers and consultants who want that.

Matthew- I agree. I completely agree. Though there are others who would say, "You know, what, I would rather have more flexibility than more stability." And I understand that position, too. It's not the position I take, but I understand it.

Wudan- For sure. So let's talk about the benefits and, say, the drawbacks.

Matthew- Mhm.

Wudan- Since we're already on that topic. How do you see those things for yourself?

Matthew- Sure, love the question. And all this will be underscored with the fact that these are different for everybody.

Wudan- Everyone, yeah, depending on the company.

Matthew- And the human. I would say the benefits for me, I can think of five. The first would be that you live with the outcomes of your decisions. And this is actually the one aspect of consulting that I like the least. I love consulting in general, or else I wouldn't have done it for 27 years. But when you're a consultant, you're kind of a professional recommender. You say: "Hey, I think you should do this thing." But you're not really responsible for the outcome. And what I do like about the fractional role is, now that I've been in it for 16 months, I have history. I can look at decisions I made the first couple of months and see how those played out. And I'm responsible for those decisions. And I can adjust accordingly. So that's one big one for me. And that's, I think, the biggest piece of the client side history that I really enjoyed, was you made decisions, and you've lived with their outcomes. And I think that's very important. Second benefit is just the steady and predictable income.

Wudan- Mhm.

Matthew- It's one thing I don't have to worry about for the foreseeable future. Third, and related to that, I'm doing less time selling, because I have this steady relationship that's ongoing. Fourth would be it allows me to do those things. To deliver value to my client while also still maintaining my independence. And I think maybe that point of balance is the big one for the fractional role. I think that's the aspect of the fractional role that's most attractive, is I can do this thing where I'm really making a difference. And also, I can maintain my independence. So it's a way for both parties to win. And then the fifth benefit, I'd say, is you have a chance to go deep in the way that you don't with consulting, which is to say in a fractional role, I'm using more of my skillset. And, viewed through a certain lens, I'm getting paid to grow my skillset, as this role requires me to grow into new things. So there's a level of depth that the fractional role brings that I think is ultimately also very beneficial. So those would be my big five benefits.

Wudan- Yeah, I like those. I like the point about career progression as well, because, you know, I think people of a certain generation may see being a CXO, like as the end-all, be-all. And it's interesting to hear you say that you can go from a consultant or a content strategist role to having a bigger role at a fractional CXO position. At the same time, even being in that position, it sounds like it can open other doors in the future, too. So kind of in the ladder of career progression, if we can just like make one up arbitrarily, where do you see this for yourself?

Matthew- That's an interesting question really, Wudan. I am the weird guy who's never really thought in terms of a specific...I was never the guy with like, "what's your five year plan? Oh, here it is, precisely." Winging it has kind of served me pretty well, for most of my adult life. And I would say the fractional role right now has been a— it was almost opportunistic. I wasn't looking for it. It came to me, and it turned out to be a really nice fit for both parties at that time. If the question is, then will I consider future fractional roles? Or will I put the focus back on pure consulting? I honestly don't know, I think I would only do the fractional thing again under very, very specific circumstances. And the number of circumstances in which I can do consulting is rather more broad. So I don't know for sure that I'm a lifetime, fractional type of dude, or if this is a one off. So ask me back in three years, and I'll let you know how that turned out.

Wudan- Yeah, but it sounds like you like the options, right?

Matthew- I do. I do very much. And again, that's one of the wonderful things about independence is—I mean, the idea of a career path in general, even 20 or 30 years ago, was just a myth. It was more of a, you know, something people wanted you to believe, than something that actually existed. And I've talked to many, many independents who are also learning that it like, it's a wonderful thing to say, hey, my business was that thing three years ago, but now I've decided I want my business to be this thing. I'm in a new season of life. I've developed new skills. I've learned more about the clients I want to work with. That's one of the things I absolutely love about this path that we've all chosen, is it really is choose your own adventure. There is no ladder. There is no journey that's identical from one person to the next. It's very much about: What do I want the business to be? And when those funky opportunities come up, do I want to grab on to that new opportunity? Or do I not? And that's really one of the joys of this. And one of the things that's kept it interesting to me for 27 years,

Wudan- I totally agree that freelancing is make your own adventure. I think in the last eight seasons that I've been running the show, people love to hear about career progression, whether that is a vestigial trait of living under capitalism, or this idea that there's always something next and something that we should be striving for. But I think listening to you talk about the benefits of a fractional CXO position, I can see a lot of consultants or freelancers being drawn to that. So I think this would be a good place to talk about ways that people could potentially work up to this role. You mentioned that you were consulting and helping companies with strategy. But could somebody who is doing content marketing get to a place like this? What are the paths, if you will.

Matthew- Yeah, it's a terrific question, Wudan. As I see it, I think there are three kinds of experience to consider in terms of working your way into a fractional role. First would be experienced in the role itself. Which is to say, I can be a fractional CMO, because I've been a full-time in-house CMO in my past. So obviously, if you have it on your resume, it's much easier for you to go to the market and say, "Hey, I can do this thing for you, the client, on a fractional type of basis." The second type of experience would be experience in the industry, where you could say, "Okay, I have not been a fractional C-suite level person, but I do have a depth of knowledge in this industry, in this niche. And I can bring that to the table. You don't need to train me. I can step into the role immediately. And then the third, and I think this will be most applicable to most people who are thinking about this, is what I would call experience at the level immediately below. So let's say you've been creating several kinds of content for several different clients over the years. You could now make a case to one or several of those clients to say, "Hey, I can manage your full calendar. I'm not just merely an executor. I can read the big picture thinking for you. I can work with other partners to get it done, so you don't have to manage those relationships. I can track the results of what we're creating. So you could pitch yourself as a fractional Head of Content, even if they've shown no interest in that role. And knowing that you'll do that, you might have a fairly low success rate. If you have that conversation four times, maybe only one client says yes, but that's one more than you had before you pitched the idea. So sometimes, you'll want to come to them and say, "Hey, here's another way for you to take advantage of my skill set. Here's a role that we could create that allows me to make your life easier, while also I deliver tremendous value to you." So that would be the third. Experience in the role would be one. Experience in the industry would be the second. And experience at the level immediately below would be the third.

Wudan- I love those three kind of categories that you've set forth. I think the third is so interesting, because for The Writers' Co-op, I think a lot of people found us because they did journalism. And that is still the bulk of what I do, primarily the industry that I work in. And so then journalists are burnt out, and they're like, how do I earn more money? And the answer is content. And then people are like, "I'm so tired of writing content. Could I make content in another way or contribute to content strategy?" Become a content strategist. And then, you know, I feel like this is, in a way, like, the next possible thing that could be interesting to explore.

Matthew- Yes, I think that's a great way of thinking about it. And sometimes I see people, too, that get trapped by the definition of what they do. They say "I am a writer, therefore I write things." And I would encourage them to say, think about, not what you do, but think about how the client gets value. Think about what you can put in their hands, what you can propose to them, that makes their lives better, that saves them time, that gets them to a better result. Because they're not buying a writer. They're never buying a writer. They're buying what the writer does for them. And nowadays, especially, there's a whole ecosystem in which writing exists. And if you can step into a higher level of that ecosystem, you are that much more valuable to the client.

Wudan- 100% agree. You are preaching to the choir.

Matthew- I thought I might be.

Wudan- Yes, yes, yes, deliver value is definitely a thing that we've been beating our drum about over here. So Matthew, I'm curious now that you've been a fractional CXO, I'm just curious if you were to look for other jobs like this in the future, what are some green flags? What are some red flags? Yeah, just I'm curious to hear what you'd find exciting. And what you'd be cautious about.

Matthew- I think the big green flags for me are very similar to the ones that I look for in a consulting gig, except that they become more important, because in a fractional role, you're much more embedded. You're much more part of the team. So for me, it's things like: Do I believe in the mission? Am I aligned with what the client company is here on Earth to do and achieve? Do I like the people, frankly? Are they fundamentally good humans? Would I want to spend even more of my life with people like this? And do I genuinely have a chance to make a difference? Is this a way where I can kind of bring in, not just my skill set, but kind of the top of my skills pyramid, as I would call it. You know, can I do my best and most valuable work with these people? They fit with my values. They fit with my preferred ways of working. That's the environment in which I'm going to do my best work. So those are also the projects where I'm more likely to get rehired and referred and that virtuous cycle just kind of continues. So for me, it's, again, kind of the same checklist I'd have for consulting. But I'd want to vet those things even more closely. Because the fractional cmo relationship is going to be a deeper and longer relationship than a consulting relationship. So I want to not just trust my gut on this kind of thing, I want to verify. That's why with Bob Rogers Travel, it was an easy yes. Because I have 12 years of history with these wonderful people. I know what they're about, you know, they're making students happy with life-changing trips. They're making life easier for the teachers they serve, and they really believe in these things. So that's an easy yes. If somebody came to me and said, "Hey, do you want to be fractional CMO of my cigarette startup?" I'm going to say that's a quick no.

Wudan- That makes a lot of sense. Just a really quick question: In these fractional C-level positions, do you own shares in the company?

Matthew- In my current structure, I do not. It's simply an hourly type of relationship. And generally, I would advise against that.

Wudan- Oh, okay.

Matthew- So for a consulting project, I'm always pricing by the gig. I want to price by the value, you know, I would do X by Y for Z. That is one of the tricks of the fractional relationship. At some point, you're gonna have a conversation about how many hours are you investing in my business? And what is that worth? So the trick is to make sure that whatever the hourly rate you land on, if you structure it that way, is above the level that you need that to be for your business to be sustainable. So I would not advise that you take a bare bottom rate for a fractional gig, because it is more hours. Because we are not tiny little factories, you know, things don't get better, the more hours we put in. We just tend to get more tired. So that is a key part of the relationship too, as you're thinking about a fractional relationship. Can I do it at a price point that fits the overall sustainability concept of my business?

Wudan- Yeah, my question about shares is kind of, you know, thinking about canonical C-suite positions, that most of those people have shares in the company. But it's just so interesting. I mean, I think from our conversation, I'm gleaning that there's no one-size-fits-all definition for what a fractional CMO or CSO, or even CFO, Chief Financial Officer, could be necessarily. It all depends on how the negotiation goes and what kinds of things you want and value and vice versa from the company.

Matthew- Yes, would completely agree.

Wudan- So we've shared a lot of—"we"...YOU have shared a lot of advice on how to get to these fractional C-suite roles. What other advice that we maybe haven't covered yet would you have for others who would want to work their way to a fractional CXO role? How can small business owners or freelancers find a fractional role that aligns with their values or requirements?

Matthew- I would say first: Know that it's a a fairly rare thing. Like we discussed earlier, there's not really a job board for fractional roles. Companies aren't always looking for fractional as the first hole to fill. Sometimes you have to suggest it. And frankly, the market need simply isn't there. So there's, you know, the number of companies who are looking for fractionals is much, much smaller than the number of companies who are looking for a full-time role. The second consideration is that, I think, anyways, these roles are more likely to come from people who already know you and your body of work. Or people who know people who know you and your body of work. And this is one reason, you know, I'll come back to the concept of fit with your values. Fit with your skills pyramid. Fit with your preferred ways of working. When you're making sure to check those boxes on all of your projects, then you're doing your best work with people who energize you and have a mission that engages you. And people like that tend to know people just like that. So choose your clients carefully, always, just because there are a lot of reasons to do so. But if you have done that, then I think you're probably better set up for a fractional type of role. Because now you're plugged into a network of people who share your values and your ways of working. And there are people in that network who trust what you do and how you do it.

Wudan- I love that.

Matthew- The third and final concept would be, as we discussed earlier, sometimes you just got to ask for the order. Sometimes you'll need to suggest the fractional role to a client just to see what they think. And again, you won't get a yes every time because that's not how life works. But it only takes one or two yeses to really put you on this path. And if you do it once, and you say, hey, you know what, that fractional thing maybe is not for me, then that's good to know, too. So now you know, for the next X number of years, you don't have to be thinking about that. You can consider other opportunities. You can go back to what you were doing before. But very rarely, I think, will something happened in the way it happened to me. I've well aware, that was just basically something falling into my lap. If I were to go out and look for a fractional CMO role, I would go to my network of people I trust and say, "Hey, I'm looking for this kind of thing. Is it a fit for you are somebody you know?" And I would expect that I would have to ask for that order multiple times to even get into a meaningful conversation about making it happen.

Wudan- Yeah, and even hearing you talk about the 12 years of working with the company before you landed in the fractional role. I'm like, wow, that's a lot of time to build trust and provide value and expertise for a single client. But you know, I imagine if anyone who signed on with a pretty regular client and keeps advocating for what they want to learn, where they want to be in their freelance careers, they can't like—the reason why I love this conversation is that it's so expansive. And just like reminding freelancers that even if a client hires them for one job, they don't have to be locked in that.

Matthew- Yes, absolutely. We're going well beyond the confines of a fractional conversation here. But that's terrific counsel for anybody at any path on their freelance career. And it's typically exactly what happens, that a client hires you for one particular thing. And if you're really good at that thing, that's what they think you do. And that's all they think you do. When really, you come to the table with this diverse and unique skill set. And sometimes you have to say, hey, here's another way I can help you grow. Here's another way I can help you hit your objectives. Here's another way I can make life easier for you. If you're not already doing it, a quarterly check-in with a client is a great time to have that conversation. If you're already talking about things like, you know, what's coming up on the editorial calendar, and things like that, you can easily fold into that, you know, "Hey, here's another thing that I do. I'm just planting a seed here. If it's of interest, let's talk. If not, I'll check in again in 90 days." But a lot of it is simply saying, "Hey, I'm here. I'm raising my hand. I know you thought I only do X. But it turns out I also do Y and Z as well. And I think those things could help you out.

Wudan- Matthew, thank you so much. That's so insightful. And I feel like I have learned a lot about fractional roles through this conversation. And I'm sure our listeners will also find this really valuable. Thank you.

Matthew- Thank you.

Wudan- Thank you so much to Matthew for coming on the show. You can follow him on LinkedIn or on X at Winning Solo. We will also include a link so you can subscribe to his newsletter. If you'd like to continue this conversation from this episode, Patreon members are already discussing it on our psychologically-safe and inclusive Slack channel. So join us. Sign up anytime at patreon.com/twcpod. Thank you so much for listening to The Writers' Co-op. This season is written, hosted and executive produced by me, Wudan Yan. The show's producer is Margaret Osborne and our editor is Susan Valot.