Chapters & Episode Notes:
0:00 – Intro
1:37 – Fractional vs. Freelance: Which One Does Your Business Need?
7:08 – How to Find and Trust the Right Fractional Hire
14:05 – Setting the Right Goals for Fractional Marketing Success
19:12 – Ensuring Fractional Hires Thrive & Navigating Tough Conversations
27:35 – Fostering Ownership & Psychological Safety for Fractional Employees
33:24 – Navigating Strategy Shifts with Your First Fractional Hire
35:11 – When to Transition a Fractional Hire to Full-Time
39:04 – The Future of Remote and Fractional Work
42:31 – Outro
Transcript:
Margaret: Marketing is essentially responsible for two functions. The first is: Are you saturating channels that your target audience already lives in frequently and consistently with a message that resonates? The second piece of marketing is: Can you identify signals of readiness, and can you get that person to do what you want them to do?
Patrick: Today, we’re going to be chatting with Margaret Kelsey. Margaret spent the last decade-plus building scalable, effective marketing programs and teams for B2B SaaS companies.
Margaret: We all had a love affair with SEO for a while, but it is a little bit more difficult and nuanced now. But it is just a channel.
Patrick: Over the last couple of years, she’s built her own business as an adviser, teaching founders and their marketers how to do the same.
Margaret: When you look at marketing as just the visible, external application of marketing instead of the machine that you’re trying to build, it’s easy to be very chaotic and kind of get thrown. That creates a level of what I call “executive thrashing” that’s really difficult for a team.
Patrick: In today’s episode, we’re going to explore: What is fractional help, and when might you want to hire a fractional employee? How do you trust a fractional employee, and how much lead time should you give them to prove their strategies? When might you want to bring on a fractional employee full-time? And at the very end, how will fractional help evolve over the next couple of years?
Margaret: A freelancer—you might bring them in and say, “I need you to accomplish this set of tasks.” Whereas fractional is somebody that you’re bringing in to really feel like they have ownership over the results.
Patrick: Hello, everyone, and welcome to another episode of plugin.fm, where we extract key lessons from top entrepreneurs to inspire your business growth. My name is Patrick Rauland—I’m an e-commerce expert and educator—and I’m here with my co-host, Goran, a content marketing specialist and the CMO at Freemius. Let’s get into the episode. Welcome to the show, Margaret!
Margaret: Thank you so much for having me.
Patrick: I want to get right into fractional help because I think it is totally underused, and other people this season have already been talking about it. So, you have been on both sides—you have been fractional help, and you have hired fractional help. What is it, and when do you think a company is ready for it?
Margaret: Yeah, so fractional is—I think of it as a little bit maybe more strategic than freelance. But it’s anytime that you’re bringing somebody into your organization as not a full-time employee. You have a specific set of outcomes that you want to get, and you know that there’s somebody with that specific background that you can bring in on a part-time basis to accomplish that.
So, if you get up to the really strategic level, like a CMO, you’re going to be delivering them a set of outcomes that you want to see, like, “Hey, I want you to build out our marketing strategy and the initial functions of it.”
But even if you’re thinking about bringing in, like, a fractional podcast lead, you’re going to set them up with certain measures of success. And so, I don’t really think of fractional as, “Hey, we don’t even know what’s going on, or we don’t know what to do”—that’s more of an advisor. I think once you’re set up and have a clear direction of what you want to accomplish, that’s when you would bring in somebody fractional.
Patrick: Let’s quickly jump into the difference between fractional and freelance. To me, I feel like a fractional employee owns a lot more. Is that the right way to think about that?
Margaret: Yeah, exactly. They have more ownership, whereas with a freelancer, you’re really just giving them tasks. You’re saying, “Here, go do this one thing,” or, “I need you to execute on this plan.” I think of fractional as having more ownership and more skin in the game in terms of actually achieving the desired outcome.
So, a freelancer—you might bring them in and say, “I need you to accomplish this set of tasks.” If you decide that’s actually not working for your strategy anymore, you might pivot. Whereas fractional is somebody that you’re bringing in to really feel like they have ownership over the results.
Goran: Thanks for that. So, in my experience—because, interesting story—I started at Freemius as a fractional CMO first. And what I noticed, because I had other fractional roles before this, is that most people tend to put an equal sign between a fractional CMO or marketing lead and an advisor, which I don’t think is really the same. But just for the sake of it, can you explain the difference between someone who is fractional and someone who is just an outside consultant or advisor?
Margaret: Absolutely, and I’ve done both with my own business—I’ve been advising, and I’ve been fractional. I think it is about that ownership piece.
As an advisor, you get to come into conversations, diagnose where things might be going wrong, give advice, and then leave. It’s up to other people to actually implement it.
I think when you’re fractional, you’re actually coming in and implementing—changing systems or processes internally—and you have the agency to have those conversations and make things happen. With advising, there really is almost a sense of freedom. I loved my time advising because you get to go in, give great advice, and then it’s up to the folks to either accept it or not.
Patrick: I have a love-hate relationship with advising because I would say 80% of the time, it’s not.
Margaret: Yeah, I know. So, yeah, where I felt a little bit of freedom, it can also feel frustrating to have continued conversations where you’re pointing out the same thing and saying, “Hey, remember six months ago when I told you this would be an issue?”
That is exactly the conversation. So, how do you know if a business is ready for fractional? Like, do you need to be hitting problems, hitting upper bounds where you stop growth, or how do you know that you’re ready?
Yeah, I think if an organization has a clear understanding of their problems, then they’re able to find somebody fractional with the skill set to create change or manage those problems. I think the hardest thing is if an organization is really sitting there thinking, “I don’t even know the first thing to do,” because then you need somebody who’s really generic.
If we’re talking about the CMO level, there are so many different types of CMOs, right? And then, even if you go lower than that, there are so many different types of owners of different marketing programs—whether it’s content marketing, demand generation, or even marketing ops.
So, I think once an organization has a handle on the problem they’re trying to solve, they can find a fractional person with the skill set and background needed, rather than just a generalist to come in and diagnose the issues. I think that’s where fractional really helps—if you can find that exact skill set that you know will solve your problems.
But if you’re just sitting there in the ether, like, “Everything’s messy, my hair’s on fire, and I have no idea what’s wrong,” then you’re not ready to hire fractional yet. You have to do a lot of that diagnostic work first.
Goran: So, would you say that getting an advisor or a consultant is a step before getting someone fractional?
Margaret: Exactly, yeah. A lot of the time in my advising work, we would diagnose what the next thing in the marketing function needed to be built—or whether the issue was actually a lack of leadership and ownership over those top-level things. Then, we would bring in a fractional head of marketing or a fractional head of whatever function needed to be built out.
Patrick: Okay, so I think I understand the “when.” I think my next question is maybe the “who.” So, you understand you want to hire someone fractionally—to me, actually, the biggest problem is trust. How do I trust this person?
Margaret: I mean, isn’t that constantly the struggle of marketing? Can we give them enough time to actually prove that it’s working?
It does depend on the function you’re hiring a fractional person for, but I think you have to trust their past experience. Fractional is rarely something where you want to take a chance on someone new.
For internal roles, I’m very willing to give someone a chance to do something for the first time. I’m really interested in pulling people up and giving them the next great opportunity. But when you bring somebody in fractionally, you want them to already have that experience and be able to replicate it.
So, their background, track record, and history are really important. I also think being a fractional worker is very much a relationship game. The more you can get warm intros to people who have worked with them before and built that trust level, the better. It’s not like the big funnels that marketers build for companies—it’s very much like, “Oh, hey, I know somebody who can help you out.”
It does take a lot of networking to find the right fractional person, but it’s built on trust. I would also say you don’t want that fractional person to have more than two to three clients at a time. Three might be the max for fractional, right?
You probably want them for 15–20 hours a week, and how can they do that for more than two companies at a time? Ideally, they have one main client and maybe some other projects, but they just want to give less time to an organization than a full-time role. So, I think that’s definitely how you go about it.
Goran: Yeah, so when you, for instance, find yourself in a situation where you’re hiring someone fractionally, would you prefer that person already having some experience in fractional roles, or are you just looking at their overall skill set and success when they were full-time?
Margaret: Yeah, no, they could be first-time fractional. I’m totally fine with that. I just need them to have run that program at that altitude before and have some success attached to it.
Goran: Cool. So, my follow-up question is—this is a podcast that has a lot of techy people listening, and most of them are not really super experienced in marketing. They know that marketing is an important factor, so can you share some of the early successes that a tech founder should look at to understand if the fractional relationship is going in the right direction or not?
Margaret: Yeah, I mean, it is so dependent on the type of marketing or the channels that you’re going to engage with in terms of what success would look like. Normally, when I’m starting out with a non-marketing-background founder, I really try to reset what marketing is at the highest level. So, I say marketing is essentially responsible for two functions.
The first is: Are you saturating channels that your target audience already lives in frequently and consistently with a message that resonates? That takes all the marketing jargon out of it, right? We’re going to pull all the way up—we’re not going to call that brand, we’re not going to call that awareness. Sometimes I call it saturation. But are you showing up in the channels that your target audience already lives in frequently and consistently with a message that resonates?
There are a lot of things that you have to figure out there. You have to have a defined target audience. You have to understand how they walk through the world and what they bump up against every single day. You have to understand the channels they value and the ones they listen to, experience, or live in—it could be events or whatever. And you have to know what your message is and whether or not it resonates. Then, you have to measure how consistently you’re showing up.
So, that is a big function, and there’s a lot of assumptions that you already have that figured out.
The second piece of marketing is: Can you identify signals of readiness, and can you get that person to do what you want them to do? Can you get them to talk to your sales team? Can you get them into your product? Can you get them to become a customer? Can you get them to sign back up? Can you get them to expand in their ACD?
That second piece is the conversion-focused part of marketing, and most people focus there. I think a lot of founders want to focus there, but depending on what kind of marketing programs you need to build, you would find somebody for those pieces. It could be one person in charge of the entire thing, but there are success metrics in each one of them.
How confident are we in our target audience—that it’s actually the right person to sell to? How confident are we that the channels are the right ones? How confident are we in our messaging? How confident are we that we understand how they make decisions and what influences them? And can we actually create marketing programs to get them to do something rather than just hear about us?
So, there are success metrics within each channel. Ideally, you want to break it out like that and then have somebody recommend and say, “Hey, I’ll be able to show you the success metric based on the work I’m going to be doing.
Patrick: Wow, I really like that reset there. I think, if I could summarize—if I could distill what I think other people think of marketing—it’s just getting people to your website. Like, that is ultimately all they care about—just eyeballs on the site. And that’s a very superficial way to look at it, but it’s just eyeballs on the website.
Margaret: Yeah, well, and that’s the thing. We all had a love affair with SEO for a while, but the reason we loved it was because it was a very easy way to grab somebody that was showing you a signal—they were searching for the things they cared about. You could get them to your website, and then you could get them to do something you wanted them to do, right? Sign up for your newsletter, get into a demo—whatever it was.
So, I also like to pull that up: that was a channel that worked very well for a while, but it’s a little more difficult now. But it is just a channel—it’s not the end-all, be-all. I think a lot of founders, when they see marketing tactics out there—whether it’s saturating LinkedIn or whatever the new marketing excitement thing is—think, We need to create a bunch of blog posts, we need to create a bunch of newsletters, whatever it is.
I like to bring it back to: That’s just a channel. It might not even be a channel—it might be a tactic that they’re super in love with. We need to post on TikTok! Maybe you do, but maybe you don’t, right? I think that’s the hardest thing—when you look at marketing as just the application of marketing instead of the machine that you’re trying to build, it’s easy to be very chaotic and get thrown around. Then, you read a LinkedIn article and think, We’ve got to go in this direction! That creates a level of what I call executive thrashing, which is really difficult for a team.
Goran: Yeah, how do you actually survive that in a fractional role? For instance, I’ve worked with a lot of businesses of all shapes and sizes, and in my personal background, they were focused on the numbers. In my mind, the reporting we have now in marketing is very broken—very surface-level and superficial. And even as a marketing person, you can gamify it if that’s what you really want. So, how do you get consensus with people that we first need to build a foundation before we can build a house?
Margaret: So, at OpenView, we split out goals into two different categories that I think were really effective and helped people wrap their brains around it. We had vital goals—things we had existing numbers, data, and metrics on that we were trying to improve.
And then we had change goals—things we would do for the first time, where we actually had no idea if the set of activities would have the intended effect. For those, we measured success based on whether or not we stuck to the work plan of the intended activities—not whether those activities actually influenced the outcome. We would then look at it and ask, Is this something we want to continue, or do we need to pivot?
The first time you’re collecting metrics on anything—anything you’re doing for the first time—it’s hard to goal a team specifically on actually improving them because you have no understanding if that’s the right set of activities or not.
So, goal your team on following the plan that you think is the best one to change those metrics. Then, they can feel successful even if the metrics didn’t improve in the way you wanted. That sets them up for this culture of creativity where they say, Oh yeah, I still won. I still did it. We didn’t actually improve it the way we wanted to, so we’ve got to try something new. But it’s not that they failed just because the metrics didn’t improve—we were doing it for the first time, so who knows?
But a lot of organizations do have ongoing programs where they have enough data to say, This is working, but I want it to work better or I want it to be cheaper or I want to spend fewer hours and have it work exactly the same way.
So, then you create a goal around that: Can we find cheaper resources to do the same thing? Can we automate some of this? Can we improve the metrics by doing something a little differently? But those are two separate sets of goals.
Patrick: I had an experience—this was a few years back—where I was building Facebook ads for a company, and my goal was like, “Let’s just get through the process. We’re going to have 20 different ads. We’ll learn a little bit from the natural A/B testing in Facebook about which types of ads do better or worse, then we can focus on profitability later.”
A week before I launched them, the CEO was like, “Oh no, these need to be profitable immediately.” There was no learning phase, and then we figured out how to optimize. It was, “Oh no, no, no, we expected this to be a winning campaign immediately.”
I don’t want to say impossible, but it’s just… it’s a very different mindset to try something new and expect it to perform immediately. Seems like a recipe for success. I think as an owner of a business, you want to give people that.
Margaret: Yeah, I mean, that is ideally the outcome, right? Because you are so confident that that is the right channel. You’re so confident that that’s a channel your target audience is already in. You’re so confident in the fact that your message already resonates that, yes, of course, when we turn this on, we’ll have profitability immediately.
But there are a lot of assumptions in there. And if you haven’t built out and experimented to make sure that each one of those assumptions is true—especially, is your message resonating?—then it has to be experimentation.
And I do think what you’re getting at, Patrick, is this idea of executive alignment, and that is very, very difficult to do. Because sometimes, especially when I was advising, I would have similar conversations and see heads nod around the table, like, “Okay, okay, we’re good with this. This is a brand program—it’s just about saturating and priming and making sure people know about us and like us.”
And then we would get to the goal-planning session, and they would say, “But these need to produce leads. This program actually needs to be measured in terms of how many leads come from it.” And, you know, you kind of have to have that conversation again.
I do think that marketers uniquely have this skill set for executive alignment, but they’re just pointing their attention in the wrong place. We know how to find out who our target audience is, right? We know how to understand the words they use, the language they use, what’s important to them.
We do this for our external audiences, but very rarely do we spend the time to actually write that out for what our executives care about. What does my CEO care about? How does he or she communicate? What are the metrics they are most pressed by the board on? And how do I make sure that I frame this in a way that they feel comfortable with?
But we don’t take the time to do that. I do think that marketers have that skill set intrinsically—we just need to start pointing it in the right direction.
Patrick: Okay, so I did want to change directions a little bit here. If you hire someone, what are the things that you’ve learned? If you hire a fractional person, what are the things you’ve learned to help them succeed? Part of me is like… is it Monday, Wednesday, Friday full-time? Or is it half-days each day? Or is it—you know—you do want to hire someone fractional, how do you make sure they succeed?
Margaret: I don’t think there’s a set schedule of like Monday, Wednesday, Friday, or half-days, or whatever. I think it works best for that person’s schedule, probably. And they’re probably most interested in fractional because they want to have more ownership over their schedule and being able to do certain things.
So I’m not hard and fast on exactly what that meeting cadence should be. I think they should be involved in—if it’s a fractional CMO, head of marketing—they need to be involved in any of the weekly meetings of the leadership team because they need to have that context. And then, if they’re managing anyone or managing different programs, they need to obviously be involved in those team meetings as well to make sure they have the full context.
Outside of that, I do agree with you that they need to be out of other, like, silly meetings as much as possible. Thankfully, now we have so many of these AI assistants that can join meetings and give them a summary and things like that.
Like, I just had one join—kind of an advising client of mine that’s on pause—and they joined a meeting. Instead of me having to go through that meeting, I got an email summary of what was discussed and what kind of came to be in that meeting. It took me five minutes instead of sitting in a 45-minute meeting.
So, we have the ability now, especially with technology, to give people more context in an easier way than what we used to do, which was have everyone sit in every meeting.
If you don’t think that person’s going to contribute to the meeting, but you think it’s helpful context for them to understand, have them set up one of these AI assistants. Have that AI assistant join the meeting. They can review the summary and have all that context in a very short period of time.
Patrick: How do you give people all the context they need to understand that, like, three years ago, this person did this thing, and that’s why we now do this thing this way? Because sometimes, it’s… I guess I think a lot of businesses accidentally create bad processes as opposed to intentionally. So, how do you give people the right context so they can fix these mistakes—fix these process mistakes? I guess that’s the right question.
Margaret: Yeah, I feel like the way you framed that—like, once you uncover that—the way you framed it is great, which is just like, “Hey, listen, this is something that, legacy-wise, I understand that we’ve always done it that way, but let’s just try it in a new way and see what happens.”
That does change. That is, it’s totally affected by the culture of the team—whether or not they’re open and receptive to that. Setting the stage when you first come in—that that’s going to be some of the work that you’re going to be doing and that it’s no judgment, that, you know, there will be optimizations.
Startups especially move really quickly, and like you said, sometimes it’s not intentional—sometimes it’s just default, or somebody didn’t know and, you know, set up a pattern and taught a bunch of people how to do it in a way that could be optimized. And I think that’s the way to frame it, too—it’s just like, “Hey, what got you here isn’t going to get you to the next place. And there’s nothing wrong about what got you here, right? It’s totally great. But there are going to be opportunities to improve, and that’s going to launch us to the next place.”
And so there’s no judgment on the fact that it hasn’t been done right before, because the organization still exists. And that’s the whole goal of startups and businesses—to survive, right? So it’s like, “Cool, you guys are here. That’s awesome. You’ve done lots of hard work to get here. But let’s go to that next level, and we will have to change things inevitably to get there, because that’s how you grow—you change.”
Goran: I think, like, a natural follow-up to this question is, how do you basically kind of have that first hard conversation?
For instance, in my experience as a fractional CMO, I come to a situation where a company has, like, an idea—like, what they do and what they want to invest in and how this could kind of get them from A to Z. But obviously, when I do some analysis and look into what’s really going on, we have that conversation that is actually, you know—you have to kind of drop a bomb.
For instance, they wanted to invest in a new content program, but actually, in my experience, I’m not naming names, they had a duplicated knowledge base that was creating a monster of duplicated content. That’s obviously, you know, a freak show.
So how do you kind of have that conversation where, like, you know, you are actually getting in the door with a proposal, but you have to kind of completely spin it?
Margaret: Yeah, I think you have to align on the business outcomes and the business goals rather than the workstream itself.
So you say, “Hey, listen, I think we all want to grow, right? We all want to make sure that this is set up and optimized and we have a sturdy foundation in order to be able to do the fun projects, right? And I’m sure duping content—you know, duplicative content—is not fun. That’s not what most people are jazzed up to do as a workstream, right?”
Yeah, but I think if you can—especially at the executive level—you pull it all the way back to the business goals, and you can point out the risk of it, right?
“If we continue as is, and we just do the fun projects and we don’t do any of this—you know, like, there’s marketing debt, just like there is tech debt, right? Because a lot of marketing is using technology these days.”
So you can pitch it as that, which is especially useful in a founder’s brain if they are from an engineering or product background. You can frame it as tech debt, like, “Hey, we have marketing debt the same way that we have tech debt.”
And that might be old messaging that we’ve never actually gone back and revisited. It might be existing programs that should be cut and eliminated to make room in terms of bandwidth and budget for new experiments and things we can do.
It could be actual tech debt—your analytics, your CRM, duplicative content, or whatever it is. It could be SEO tech debt, or whatever it is. But they do understand that idea—when you run really quickly and you’re just building, building, building, you accumulate debt that you then need to pay down. And so, we need to pay this down in marketing before we can do any of the fun projects.
Patrick: I haven’t had much success in getting people to understand that message. I don’t think I’ve been the right person to communicate that to the executives and get them to listen in my previous roles. So I’ll have to bug you for some specifics on how to talk with executives.
Margaret: I’m maybe successful at this 50% of the time. Like, getting executive alignment—even though I said that marketers do have a unique skill set to be able to do it well—it doesn’t mean that you always also get your way, right? Or that you’re ever really… It could be that they say, “Yeah, I totally understand that, but we keep building. I don’t care about marketing debt.”
And so how I think about that, especially when it’s a founder-CEO, is: ultimately, anyone working for somebody that started a company is working in terms of building that person’s vision. And if you have different visions and you cannot align, you can either disagree and commit, or you can find another organization that you know you’re really aligned with.
But I do have a sense of—like, I don’t know if it’s a boundary or just a sense of peace with the idea—there are people out there building their dream, building their company, building their mission and their vision. And if I wanted to do that by myself and I wanted to make the final decision, I should go start my own company, right? Start my own software company and build it from scratch.
Ultimately, anyone that’s employed at a company is following the person at the top’s vision. And it’s totally fine if you have a different vision and you can’t disagree and commit, or you can’t influence it in the way that you want. But you have to make that decision on whether or not that’s the work that you want to be doing or you’re willing to do.
Patrick: To me, a really good employee is someone who has ownership—who cares about something. Again, it’s like, you own this thing, you care about it more than a freelancer, right?
So I guess, how do you get a fractional employee to have ownership and update that piece of content that hasn’t been updated in seven years?
Margaret: You know, when you bring in somebody fractional—yes, they should have ownership, and that is based on personality, right? Some people just have an intrinsic feeling of ownership more than other people do.
But also, maybe there is some kicker—some benefit, some bonus structure to a fractional role—if they do actually influence the KPIs or influence them in a way. So that they’re—you know, I do think what gets measured gets managed. And so the more that you can give them KPIs or metrics the same way you would give an internal employee, the more that they’re going to have that sense of ownership.
But also, they’re going to feel more comfortable that they’re actually contributing and that their job safety is there, right? If they know that they’re responsible for this core metric and it’s improving.
Patrick: Love it. So I did want to get to psychological safety, so I’m glad you just helped us transition there. So, on any team—especially when you’re doing creative work—I feel like psychological safety is key. And just to define it for people who haven’t heard it, it’s the ability to voice a concern or a dissenting opinion and know that you’re not going to be punished for it. Is that kind of a decent definition?
Margaret: Yeah, being able to kind of share freely without fear of punishment, retribution, or anything else. Yeah, for sure.
Patrick: So how do you instill that in, again, a fractional employee—someone who’s recently joined the team and needs to have some creativity, possibly be wrong?
Goran: And very easy to cut if—like, we real…
Margaret: So sometimes, I’ve actually—I’ve seeded that in team conversations before, where I will have somebody challenge me. I’ll talk to somebody on my team beforehand and say, “I want you to challenge me on this point so I can show what the reaction would be,” right?
Zero to one on psychological safety is tough because nobody has any data points on how it’ll go, right? So I have done that before, where I talk to one of my teammates beforehand and say, “Hey, I want you in the meeting to challenge me on this so people can see how I react.”
And that opens the floodgates of people feeling way more comfortable to be able to do it. And I think another thing is—it really is about the leader’s emotional reaction and ability to emotionally regulate and to be curious, right?
“Hey, are you seeing different things than I am? Like, I came up with this plan, or I came up with this direction, and I’m pitching my team on it. But if you have different data points than I do, I want to be curious about where you’re coming from. Do you have a different background? Do you see different things at different organizations?”
And that’s the mindset of a leader that I think prompts that emotional safety—really being curious instead of reactive or thinking that you somehow have all the answers.
Because odds are, the folks that are actually doing the work on a daily basis have way more context than you do—if you’re doing your job right, right?
Like, I feel like as a leader, you have the context of the business goals, and you have the context of the business challenges at a different altitude. And ideally, you are pushing that down to your team in appropriate timing and appropriate doses.
And, you know, you’re not saying, “Hey, we’re about to run out of money—everyone leaves the job,” but you want to filter that appropriately.
But ideally, they have as much context as they need to do the work. And they have all of the data on a daily basis and all of the stuff that they’re seeing, so they’re actually probably better at making decisions about their functions than you are.
Patrick: I don’t think I’ve ever heard of someone seeding someone to challenge them to demonstrate psychological safety, so I just wanted to give you some kudos for that. I have managed people in the past, and I would always try to make fun of myself to make it clear that I can take a little bit of criticism, but I think having someone challenge you is an even better idea. So I really love that.
Goran: But from the other side—because, like, let’s say people who are listening to this podcast probably are exploring getting someone fractional to kind of help out with marketing—does this also imply that you have to be kind of open to being challenged as well to make this work?
Margaret: I think, as human beings, we all should be open to being challenged all the time, but I understand that that’s just—you know, I think, yeah, I think everyone should be in therapy. I think everyone should be working on their own stuff, and I think everyone should kind of work on their ego and be willing and curious.
I understand that that’s not necessarily the workplaces that we live in, but ideally—especially coming from the person who has, you know, been fractional and has been on the employee side of it—it’s also really beneficial that you get to make the decisions on who you work with, right?
You get to meet the team, you get to meet the founder or the CEO, you get to meet the other executives, and you get to kind of test out whether or not they’re willing to be challenged.
And I think good people will naturally go to teams where they can voice their opinions and voice their challenges and feel that sense of psychological safety. And then those will be the companies that win because they’ll have the best talent.
And so it is actually—there is business value to founders and CEOs to work on their ability to be challenged because you will have better business outcomes.
Goran: Yeah, but like, in the context of, let’s say, you’re getting to your first fractional hire—so it’s like your sixth step into kind of prepping to get to that part—and you have a strategy and a vision, and then someone comes in and does, like, a massive pivot. That can be, you know, obviously hard to swallow.
So, yeah, I’m just thinking—does this actually mean that you should either look for someone who will be with full open arms, or should you kind of look for someone who agrees with the certain points that you talk about?
Margaret: Yeah, again, that totally depends on the level of person that you’re willing to bring in.
I think if you—let’s say you had an advisor, let’s say you figured out, like, “Hey, this is actually kind of the type of fractional CMO that we need based on their skill set, based on what they’ve seen,” and then that person comes in and says, “Hey, actually, I have a different plan for you”—it’s probably still within their skill set, right?
They’re not going to say, like, “Hey, you brought me in as—like, my background is in brand, content, and community, and I’m going to do all these conversion-focused demand gen programs,” etc., etc., and like, “We really need to focus over here.” It’s probably a subtler tweak than you would think.
But if you are bringing somebody in at, like, the topmost level of marketing to be a fractional head of marketing, and they’re telling you that you need a different set of programs or work streams, I think it is open—like, you should be open to listening to them. You could also decide then, when you listen to them, “Hey, I’m not fully convinced; I’m going to go find somebody to actually do my plan.”
And that goes back to that idea—it is the founder or CEO’s vision. You know, they do get to point people in the right direction and find the right resource for what they think is best.
Patrick: We’re getting near the end here. I was curious—is there a time where, let’s say, you hire a fractional marketing person, and in six months, all the gears are firing, everything’s moving forward, the business is growing, life is good.
At what point do you want to, like, convince them to bring them on full-time? How do you know when it’s ready to—like, I guess I want to say “take it to the next level,” but maybe that’s not quite right.
Margaret: Yeah, well, I feel like, obviously, financially, when it makes sense.
But you’re probably paying somebody fractional pretty close—because you only want them to have one or two clients at a time—you’re probably paying them pretty close to full-time anyways. So I know that it’s usually not so big of a financial leap to bring them full-time. But obviously, you want to make sure that your budget and your growth support bringing that person in full-time.
And I think by then, the benefit of fractionals is that you really get to test out that culture fit before you’ve ever invested in someone. And then when they come on board, they don’t have the onboarding that a new fresh hire has, right? They have more context; they’re able to just put more, you know, fuel on the fire, so to speak.
So I would say it’s definitely a business decision on whether or not you want to keep them fractional versus bring them in full-time. It’s usually not a huge decision, but you get to—you know, when you fall in love with that person who’s doing that role, you know, just try to wheel them in, reel them in.
Goran: So would you say that starting off fractional is actually a good way to kind of scout for someone full-time? Like, if you, for instance, are looking to hire your next marketing leader, do you advise people to actually start with a full-time—it’s basically a test project?
Margaret: Yeah, I mean, that has to work on both sides, right? There are lots of people that just want to get hired in full-time. There are lots of people who have kind of been around the block, especially in tech, and are a little exhausted and want to make sure that it’s the right fit on both sides before they put all their eggs in one basket.
So I think it has to work on both sides. I would never say, like, you have to do fractional before you bring somebody in full-time, but there is a real benefit in that, on both sides.
You kind of get to test it out and make sure it’s a good fit before you have somebody in—then have to, you know, think about employment law and all of those things in order to fire them if it’s not working out. And, you know, I think that there are a lot of people, especially in tech, who are a little more hesitant, a little more reserved, and really want to make sure it’s a good fit before they join. And I had something else to say about why it’s so beneficial for the person on the fractional side—oh! I will say that that’s exactly what happened with my current role.
I was fractional at Kodaris starting in February and then went full-time with them in July. And even before that, I was advising for, like, a year and a half before that.
So it was a slow play by Tony, the CEO. He knew that I, you know, had this background and—candidly—burnout from being in a lot of tech startups and then on a VC firm and then having a baby at the beginning of COVID and being a working mom and all that stuff. So he played the long game with me, and it worked. And so it can be really beneficial to both sides to kind of test it out in a trial run for a couple of months before both people are like, “Yeah, let’s go, I’m all in.”
Goran: Yeah, I think, especially for someone, as you said, who has experienced burnout and worked with different cultures, I also have to say that I appreciated doing the whole fractional thing before I fully committed.
So that I knew, like, the relationship, the dynamics, the real expectations, and the real, you know, situation and culture.
Patrick: So I want to get into the last question here. So, Margaret, you’ve seen the evolution of remote work and distributed teams. I would just love to—where do you paint a picture for—where do you think this—where do you think remote work and fractional work evolve in the next couple of years?
Margaret: Yeah, it’s really funny because I did start remote at InVision before remote was cool. It was a decade ago. My mom was, like, not convinced that it was a real job.
I’m like, “I don’t know, they sent me a computer. I do stuff on it all day long. The direct deposit hits my bank account. I’m pretty sure this is real,” you know? But it was such a different way of working back then than we were used to. It was actually even before we had Slack—we had Skype. I was like—my onboarding was, “Here’s 35 people to add on Skype,” and that was how we did it before Slack.
I will say that at the time, it was very clear that remote work was a skill set. There were a lot of fantastic people who joined InVision who couldn’t cut it in a remote setting but were very, very fantastic in an office setting, right? Like, it’s not that their quality of work was bad or they were a bad human being or had no motivation—they just didn’t know how to cut it in remote life.
And so I saw that, and I was like, “Oh, this is a new type of skill set or a new type of ability to be able to do.” And then it was really interesting to watch it happen in the COVID and post-COVID days, where there was a rapid adoption throughout most companies that could have their workforce be remote. But I was keeping that in the back of my mind, which is, like, “This is not for everyone.” And so it is interesting to see the comeback-to-the-office culture, the hybrid thing going on, the total remote thing.
I don’t think that it’s a skill set that can’t be learned, but I do think it is fundamentally really challenging if you are naturally somebody that gets inspired by co-working in real life with people—to then be successful in a remote circumstance if you don’t have the skill set already, like, naturally, intrinsically within you. I tend to be somebody that absorbs people’s emotions when I’m around them, so an office—like, full-time in an office—is horrible for me.
Because I just, like, walk around, and I’m like, “That person’s stepping differently—I wonder what’s going on in their life,” or “That person just left that meeting room, and they look upset—I wonder what’s, you know…” Like, I was just constantly scanning. And so it’s really nice for me to be remote. But I also have a lot of, like—probably anxiety—but I have, like, you know, I’m always trying to prove my worth.
And that’s really good for a remote worker—to have that kind of intrinsic feeling of, “Have I done enough today? Have I shown my work today? Have I pushed this along enough to make sure that people know that I’m working?” Like, “Is my Slack status active? Do people see that I’m here and responding?”
And so that is helpful in a remote setting, because you do want people to have a bias toward putting the thing in Slack, sending the thing that’s done, or getting visibility on something that was just started to show that there’s momentum. That’s a very beneficial thing for remote workers to have kind of intrinsically within them.
Patrick: Margaret, thank you so much for joining us and sharing all these insights.
Margaret: Yeah, happy to be here. This was really fun.
Patrick: And thanks to our listeners for tuning in. If you enjoyed this episode, like, subscribe, and tell your friends so we can carry on enticing awesome and influential guests to join us and share their remarkable journeys. If you subscribe through the plugin.fm website, you’ll get early bird access to our future content. plugin.fm is brought to you by Freemius—your all-in-one payment, subscription, and taxes platform for selling software, plugins, themes, and software as a service.
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