What Benefits Come from Flexible, Non-Traditional Roles with Kristin McAlister

Kristin McAlister, owner of Serious Executives, explains how interim and fractional executives help companies solve immediate problems like sales drops or missing functions without full-time hires. She emphasizes reverse-engineering the desired outcome, then matching an executive who has delivered that result before, and warns against waiting too long to bring in help.
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Welcome to the B2B Growth Blueprint podcast, where we talk with entrepreneurs, founders, and leaders at B2B services, tech, and SaaS companies to learn the systems and processes they've used to create success for their business. And we'll also learn from marketing and sales experts to provide insights to help you grow your business. I'm your host, Mark Osborne. And the podcast is brought to you by Modern Revenue Strategies and their 10x ROI B2B Growth Guarantee. Schedule a free diagnostic call to learn the fastest path to double your B2B revenues in just 90 days. Hello and welcome to another episode of the B2B Growth Blueprint Podcast. I'm your host, Mark Osborne, and today I'm very excited to welcome my guest, Kristen McAllister. Now, Kristin is an owner of Serious Executives, and she's dedicated the last 15 years to helping companies build leadership teams that build the business. She's a speaker, a 4x author with a passion for business and personal growth. As a business owner, wife of a retired Marine, and an ultra racing athlete, she believes the best way to complete the race is to start at the finish line. So, Kristin, welcome to the show.
Thank you, Mark. I'm absolutely thrilled. We've always had such fun, energized conversations. It's wonderful to finally have that record button on.
Well, why don't you give our audience a little bit of background? Tell us a little bit of the story of what brought you to where you are today and really what you focus on today.
Thank you. I've been very fortunate that my career really has been 2 15-year stints, with the first 15 years in retail. I shifted my career in 2008 after the company was purchased and that wonderful 2008-2009 event, I— it did give me the opportunity to explore what did I want to do next. Did I want to go into consulting? Did I want to join a Fortune 500 company? Go help grow another small business? I wasn't quite sure. And through that, I did end up consulting. I realized This was not for me being on the outside. I loved working with the teams and problem solving, but then they were left to their own devices to go back on a day-to-day and actually solve it.
Mm-hmm.
And all I wanted to do was jump in and be there side by side with them to implement everything we came up with. And that's where I came across this incredible concept of an interim executive.
Okay.
Where they actually do take on a role in the company, either part-time or full-time. And the light bulb went on. It made all the sense in the world. So through a series of events and exploration, I ended up partnering with the CEO of Cirrus Executives, and we purchased the company. And that was 14, almost 15 years ago, Mark. It's unbelievable to realize what it was back then and what it is now and how commonly accepted the concept is to bring in someone on a part-time or an interim basis.
And so tell us a little bit about the work you do at Sirius. And the reason I sort of tease that up is, so a lot of our audiences, founders or operators at businesses, and they're trying to grow and scale oftentimes, or maybe they're preparing for some transition and they need some expertise. And they don't always know the full breadth of options that they have for them when it comes to leadership teams. So, tell us a little bit about the work you do, because I know you have a really sort of unique approach.
Thank you. And it's where I love it's evolved over the years to just about any expertise a company needs. They can buy, borrow, lease on any type of a basis— advisory, project, interim. The core of where we have ended up with our clients over the years and working with business owners is really from a strategic advisor.
Mm-hmm.
Advising them on how to grow their company through building the right leadership team as they go and just plugging and playing what talent and expertise as they need, who really should be in there full-time and longer term, who's needed on a part-time basis. And who's needed just to bridge a gap or bring in a specific expertise. Well, it's been amazing to really work with companies, small, medium, large, at the initial growth stages, as well as those final couple years where they're preparing for it to be sold or recapitalized and really going on to the next stage.
So it's so interesting and to think about just sort of the way the modern landscape has changed that You have so many more options rather than just, well, we gotta recruit and hire, and then we're kind of stuck with whoever we hired. Even if, you know, maybe they have some, you know, technical expertise that's needed for the team, but they're not a great culture fit, and you kind of have to adapt the culture to fit them. Today, there's so many more options, as you said, like the ability to bring someone with some technical expertise in as an advisor for a short period of time, or someone that is in a role that's important, but doesn't need to be there every day and, you know, more of a sort of fractional basis. What are some of the big benefits that you see that companies get from taking advantage of these kind of less traditional approaches to, you know, filling the needs within the company?
It really gives them a lot of flexibility on, let's look at the business and what problems we're having right now, what opportunities we want to capitalize. We don't have to pull out that job description and think through every scenario that may possibly happen in the next 3 years and find that one person who can grow with a company, who can think ahead and what's going to happen in the next 3 years. We get to focus on the next 3 months, 6 months. What problems are we having now?
Wow.
We don't need to borrow tomorrow's problems and we don't need to solve for 3 years for now. Let's solve for right now. And it may be a different person. One of the most common calls we get is, we need an interim VP of sales. Okay, what's happening? Our sales have gone down by 20%. We've gone through our Rolodex, all these things. Talking through it, what they really— they have no marketing.
Absolutely none.
The sales team has just relied on their Rolodex. So we'll end up putting in someone to establish marketing, get it up and going, someone who has established and created marketing that can really drive that sales engine. And 6 months later, once that's up and running, you may need a different marketing expertise.
Mm-hmm.
Or you may just need a marketing coordinator. You don't need to spend $200,000 ongoing. Let's now find that right longer person. now that the heavy lifting is over. And we see that scenario applied throughout a company's growth. Sometimes I was just talking to someone yesterday where their direct company has outgrown their director of operations.
Yeah.
They just haven't been able, because they've worked at that company for so long, that's all they knew, and it's the biggest company they've ever worked in. So when that company grew, they didn't know how to grow with it. Do we need to Throw out this person who's good at their job but can't help us grow? Or do we bring in someone 1 or 2 days a week to mentor, to work side by side, to do that 10% strategic and teach and develop and give that director tools? Now we get the best of both worlds.
Yeah, it's so funny. I'm actually currently working in an engagement today which is very similar where they have You know, someone that has grown with the company, reward that person's growth, but they do need some training and some mentorship. And so I can come in on more of a kind of strategic overlay basis and really prop them up so that the rest of the team starts to really gain a lot of confidence in them while, you know, helping them get some of the basic blocking and tackling in place, maybe some of the more technical things that they aren't as familiar with. Because they've been with this one company growing for so long, whereas I've had the benefit of seeing it done lots of different ways. And so that's so different than, you know, what I think people think of oftentimes in the fractional world is like, like a fractional placement company where you're, you know, basically you give us the job description, we'll find the people. It sounds like you're doing a lot more kind of sort of business strategy consulting with your clients and helping them understand what those needs are today and then how to, you know, sort of fill those needs correctly. What are some of the tools that you use in helping companies think through, you know, what their real needs are today and the best way to sort of fill those needs?
I wish I could say that we fill out a spreadsheet and we put it into this magic program and it says, here's exactly who you need.
Right.
We'll get there someday. It's curiosity.
It's— Yeah, okay.
Run a business. I understand I've talked to hundreds of businesses as the others on my team, and it's just asking the right questions because as much as we think every single business is unique, there's really only so many situations and profiles.
Yeah.
And only so many problems. And it's understanding in our network which executive has solved this problem 15 times over.
Right.
Who has the experience to get books closed 2 weeks faster, understand the entity, who to develop a team versus who has the expertise of prepping for an M&A.
Yeah.
To transition the books from cash to accrual and have it ready for a sim. Those are— those can be 2 very different individuals of developing and leading a team and putting processes in place versus M&A prep.
Yeah.
And when someone's done that 10, 15 times in 20 different companies, there's no figuring it out. They know what to do. They know how, they know how to take those curveballs and adjust because they've seen that curveball before. They know what to do in that situation. It just takes the guesswork out of business.
Yeah.
It keeps us on that offensive moving forward versus defensive and fighting fires on a day-to-day basis.
So I'm curious your thoughts on, you know, the, as you said, the, you know, the interim executive or the fractional executive, which is sort of today's current term. And I'm hearing more people talk about outsourced instead of fractional because there's somehow a sense that there's more value there. But what are some of the missteps that you've seen companies take as you're an expert in this space? And this has been growing. And so a lot of companies are sort of experimenting with it. What are some of those missteps that companies sometimes take as they think about bringing in someone on an interim or as a bridge or as a fractional? What are the doubts?
I don't even have to think about this, Mark. Normally, I would take a pause and sidestep. Biggest mistake is waiting too long versus thinking ahead, who will we need? Or where are we at waiting until the pain and the problem is so great that it's going to take 3 times as long and cost 5 times as much to solve for it? So one of the common things, especially with founders, we love to wear those hats.
Right.
And we unintentionally end up building the team around us and building our business around us versus staying out in front and leading it. So rather than pulling in that expertise as it's needed and ready to be taken off of our plates, we hold on to it too long. And it just does us, our teams, and the business injustice. And then once we do want— we're ready, we're in enough pain, we're gonna put it off. Now we have this in mind that the only person we can hand it off to is someone in our industry.
Mm-hmm.
Or someone that's just like me, or someone who has my exact experience before, versus stepping back and what's coming in the next 6 months, what problems are we solving for, who solved for them many times over, and who's maybe worked with founders before, where this is the first time someone new is doing this and they've got a methodology. to help transition that because it never looks like it when you hand it off. It never looks the same as when you're doing it, and that's sometimes difficult for us.
Yeah.
And it takes a very specific expertise to be able to do that, as I'm sure you have as you set up marketing programs and departments. It's just, it's going to be done differently by someone who's done it before or where this isn't It's your expertise. It's not the individual who started it.
It's so interesting that as you're saying that, you know, there's a phrase, and I don't— I can't exactly remember where it comes from, but it's the idea of to delegate and then elevate. And the— when, you know, so many founders, and we see this, you know, all the time as companies transition from sort of founder-led sales to kind of marketing and sales systems-led sales, is that they, just as you say, like, I got to get somebody just like me and then we'll double our revenues. And, but that's, you know, doesn't really work for lots of different reasons. But that elevate part of the delegation is so key because when you do bring someone that has done it before and has some expertise, they can actually bring new ways of thinking about it that can actually solve problems in ways that you would never know were possible to solve it. And so if you just hire for someone with your background, your experience, then you wind up sort of stuck with the same level of capability. You have just twice as many hours butting their heads against the wall instead of sort of bringing in that external expertise.
And it really brings us out of— when we're able to think about what's the outcome I need this role to create, what's the outcome I need We get to start thinking 2, 3, 5, 10 years ahead. What am I gunning towards? Why am I driving this company?
Right.
Why did I start it in the first place, and has that changed? And we get to have those really thoughtful, visionary discussions and meetings, whether it's with me, myself, and I, or an advisor that I'm working with, or possibly the executive. To think, what do I want to accomplish? Who do I need who has accomplished that before and they can show us that way forward rather than starting with what job description, what tasks do I want to take off from me and who do I go find to do those tasks?
Yeah.
Start again with that end in mind, that finish line. That's why I say start at the finish line and you've already completed the race. Now we're just reverse engineering it.
Yeah.
And it makes all those little decisions that we're weary on or that we've been holding off because what if I make the wrong one? We start at that end and work backwards. All those little decisions disappear because we're getting someone who has delivered those outcomes before. That's what matters, not how they get there.
That's right. Well, and it's interesting that you talk about that, you know, The way that they get there and having solved the problems before. Because one of the challenges that we see from the marketing and sales side is so oftentimes people will be like, well, I want to hire somebody that has built a company exactly like mine, exactly this, but they work for the top-tier company and they took it from $1 million a year to $10 million a year. So surely they'll be able to get me from $500,000 a year to $1 million a year.
Yeah.
And we're like, that's— they're very different things to do. Oftentimes one skill is creating the system, another skill is operating within the system. And, you know, one skill might be more around negotiating because you're now a preferred provider in the space versus another is more around hunting because you're trying to create a name for your space. And we, we use the joke sometimes of You know, I want that person that's, you know, already achieved it. And I'm like, do you want them to read you the lottery tickets that worked that one time? Or do you want someone that knows how to pick winning tickets and someone that's got a system around it?
It's a great— it's the brands on the resume, those logo misconceptions.
Yeah.
We hear that. I've had 2 executives. They worked for these incredible companies. They built that brand before. They've done it before. But they both failed. What's going on here? They also walked into multimillion-dollar budgets, entire team and structure in place. And then there's that conversation of, did they strategize it and figure out that endpoint? Did they create the path there? Did they just execute on it? Or were they just executing on stuff that's already proven, already in place, and they just had to do it on rinse and repeat?
That's right.
And improve on it. And you can use that for any position you're hiring in the company of, well, they've worked at these amazing brands. Let's dig it in our conversation as we're talking to them. What was the team? What was the infrastructure? Who actually made the decisions? How did you know to do that?
Right.
And you really understand where their expertise and their environment lives and what's good because they That great brand is great. That's 70%. That execution is 70%. What about that 20% to 30% of figuring out where do we want to end up and how are we going to go about getting there within the limited resources we have? Have you ever walked into an assignment or worked with a company and they said, unlimited resources, here you go?
Never.
No, we all have limited resources. And someone who can say, here's what it's going to cost and here's what it's going to take and the resources to get to that end destination. Are we going to spend— are we going to invest in this? Or maybe we just need to shift the destination for now.
Yeah.
And let's do that before we even start. Yeah, it's just—
And what you were describing, like, we see so often, like, there's a different type of person that thrives within a system that's been built versus the people that enjoy creating the system, and then they actually get bored once the system is built and they kind of move on. And so oftentimes you don't see that those people rode the wave from, you know, $1 million to $5 million. In fact, They kind of, you know, hacked their way through the jungle from, you know, 750 to 1.2. And then they were like, oh cool, now it all works. Now I'm bored. I want to get out. Someone else comes in and runs that system that they built for some time. As you work with executives and, or really, you know, sort of these company leaders that are trying to bring in an executive, how do you guide them to think through Identifying, you know, someone that thrived within a system versus created a system and how to really diagnose what they need within their company?
Fortunately, we get to do all that for them. That is, that's our really understanding what problems is the company solving for and what's going on in that company, in that situation. I just talked to someone this morning. She said, the person you put in front of me, was great based on our initial conversation. Guess what? 6 weeks later, it has completely changed. Let me update you on the situation. We need to put someone very different in front of them.
Yeah.
Just the environment, what they want to do over the next 2 years. And we know who we've worked with and we know through our conversations. So when we're putting a couple of candidates and a couple of individuals from our team, who to work with. We know that they're going to be able to accomplish it. It's just, who do you feel best about? Who do you— personality type, you hit all the right things. It's amazing what questions they'll ask to really get to the heart of what's going on in the company. You've got multiple experienced individuals just being curious and asking questions. It's not, what do you want them to What tasks do you want them to accomplish? Let's talk about some of the other gaps in your, in your leadership team and who they can help develop. Yeah, it's amazing what can be accomplished.
Well, I also bet because you, you take that really strategic and kind of empathetic approach to working with your clients, that between the 6 weeks of your first conversation, you probably unlock so many things in their head about the way they're thinking about their growth that by the time they're seeing candidates, it has evolved a lot in their mind in terms of what they now know that they need or think that they need. Does that happen a lot with you?
It does, absolutely. I always say you never learn— you never really know what you need until you talk to people.
Yeah.
And as you talk through— and I had someone once say, you talked to 3 people, 2 of them you gave me exactly what I asked for, The third one, you gave me what I actually needed, and I didn't know what I needed until I talked, until we had that conversation.
Yeah.
And on paper, they would— they were hesitant. They would have never talked to this individual. But through the discussion, he said, this is exactly where we are at. And it's going through and seeing it so many times. It's a little easier to know what questions to ask and how to get there.
Yeah.
That's where really our expertise comes into play. We get to see— we've seen it hundreds of times. We get to aggregate that experience to the benefit of every single founder CEO that we talk to, to reduce the risk of getting it wrong. None of us want to make the wrong decision, especially at the leadership level.
Right.
And at what it costs.
That's right.
Not just the comp, but to the company.
But there's a lot less risk in making that choice around, you know, a fractional or interim type of resource versus someone that you're sort of making these long-term commitments to. Not only just— I think probably a lot of just sort of mental blocks of, you know, people really struggle to fire full-time people, whereas it's a lot easier to, you Let someone in an advisory role go and, you know, sub in someone new. Is that right?
Yes. And it's— you absolutely may migrate. You spend the money where the problem is, and when that problem is no more or it's not working out, we shift our resources to over here. And it's absolutely— when you're working with them on it, we'll just call it all outsourced. Everyone's outsourced at that. Those individuals are outsourced at that point. Sometimes we just don't exactly know what we need. We've had a number of situations the last 18 months where they had someone like a director of finance. That person gave notice or left. And rather than pulling out that job description and saying, we're just gonna rehire another director of finance, they said, hit the pause button. Is that what this organization needs over the next couple of years?
Yeah.
Why don't we bring in an interim CFO to assess, to help us figure that out, to maybe do some of the heavy lifting, put some of those processes in place to develop our individuals. Do we need to restructure? And once that's in place, they'll help us figure out what we need longer term. We're not guessing. Right.
And what an honestly great environment today that gives CEOs the flexibility to do that. Because historically, that would have been really hard to do. You would have had to have relied on, you know, a really rich board of directors that had advisors that they could bring in and provide that expertise to you on that fractional basis. And then you'd have had to sort of commit to long-term hires to get that type of quality. Whereas today, the landscape's totally changed and you can bring in that really great quality to help you see around corners and then hire for the specific, you know, sort of level that you need today.
And I don't have to know everything. I don't have to have a crystal ball. I don't have to have all the answers. I've got the keys to all the expertise I need. And this is incredible expertise that really enjoys the flexibility of working with different clients, or as you said, Go and solve that really tough problem, right? Turn it over to the longer term, get the longer-term solution, and then go in and parachute into the next one. You've got different personalities and they want to be available to help businesses.
So you're obviously an expert in a lot of things that, uh, we could talk about all day, but I got to be mindful of your time. But before we let you go, like Give our audience, you know, kind of the pitch, like who exactly do you work with and, you know, what are the outcomes that they get from working with you?
We work with business owners, especially founders and CEOs who are looking to grow the business. Let me just say one leader at a time.
Okay.
Open to it. They're looking to take it off their plate. They don't want to do it anymore. or to fill in a short-term gap with a long-term strategy. And that's what we're doing. So anyone who is looking to grow with a solid leadership team to support them in that growth, that's where we can be invaluable, just talking it through and advising and helping them figure out who's the right person and what right expertise, what expertise at the right time. To learn more, and just it may be a whole new concept. What do you mean I don't need to spend $250,000? Seriousexecutives.com C E R I U S, and watch the videos, explore all the case studies, and we're happy to just have a conversation to talk through all of the possibilities, all those decisions that we've got in the back of our head, whether they're Weekly, monthly, quarterly. Let's make it a lot easier and have that high level. Where do we want to end up? What's going to take to get there? Let's look at the entire picture and then solve for it one problem and one expert at a time.
Well, Kristin, I've really enjoyed our conversation and learned a lot. I know our audience has too. Thank you so much for taking the time to connect today.
Thank you so much, Mark, and for all of your insights and what you do, because I know you see a lot of A lot of those same challenges and what you're doing to help companies and just thrive in any environment, I think is incredible. I always enjoy talking with you.
All right, take care. Talk to you soon.
Bye.
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