Parallel Entrepreneur with Mark Cleveland

Mark Cleveland (00:00)
Welcome everybody to the Parallel Entrepreneur podcast. I'm your host, Mark Cleveland. And today I'm excited to welcome Caitlin MacGregor to the podcast. Caitlin is the CEO and co-founder of Plum, a company that is revolutionizing the way organizations unlock human potential. After building two businesses for other people, Caitlin set about to create Plum to tackle one of the biggest challenges in the workforce, ensuring that people are matched to roles where they can truly thrive. And in doing so, she's helping businesses thrive as well. Caitlin's actually a force of nature when it comes to talent innovation. She's a sought after speaker at global events like CES and HR Technology Conference. She's been quoted in the New York Times, the Globe and Human Resources Executive. And beyond her many accolades, she's actually been the 2024 honoree as one of the Top Entrepreneurial Winning Women in North America. What stands out about Caitlin, at least in my experience, is her deep commitment to helping people and organizations realize their full potential. She's a leader who inspires by example, and I can't wait to dig into her journey, her mission, and the lessons she's learned along the way. Caitlin, welcome to the Parallel Entrepreneur.

Caitlin MacGregor (01:20)
Thank you so much for having me. I'm excited to be part of your show.

Mark Cleveland (01:23)
Well, and you are the attraction. Personally, myself, I've co-founded a number of companies and this co-founder entrepreneurship thing is more than a pattern. We see it more often than single visionaries launching a company. And in your case, your co-founder is your chief product officer and your husband. Let's jump right into the lessons from the desk of a CEO in co-founder dynamics.

Caitlin MacGregor (01:48)
It's really funny because most people, when they think about their co-founder being their spouse, most people go, oh, I could never work with my spouse. And in my case, it's a superpower. It's a big differentiator because they talk about how lonely it is at the top, and they talk about co-founder problems that happen later. There is nobody better to support you and to share in the experience and to fill in the gaps and compliment you than somebody that has committed their life to being happy and successful with you. So for me, it's, it's this huge advantage that I have somebody unconditionally there to be aligned to the success of the business. And, you know, we have completely different strengths. We support each other in completely different ways. And it has allowed me to, really take this journey as a long-term, marathon rather than a short-term sprint because we can, you know, support each other, not just in the business, but also in our home life to make sure that both are, that there is a healthy work-life balance, that there is a healthy, part of this journey. So much of that, being alone at the top as a CEO and doing it alone and not having the right kind of support is that, you know, it can sometimes really lead to unhealthy work-life balance. It can lead to really unhealthy habits, but because I have a partner in every aspect of my life, helping me do it right, it's, it's been fantastic. And we worked together at somebody else's business first. So we got the training wheels. We got the executive coaching under somebody else's, you know, banner and realize that it was a recipe for success to continue to work together before then doing it ourselves. So we've actually been working, at the prior business, that we built for somebody else and then decided to go into business together. And we've definitely learned a whole bunch of kind of do's and don'ts to make it a really healthy, successful relationship.

Mark Cleveland (03:45)
So you are the CEO and we were talking earlier about the CEO's journey raising funds, experiencing imbalance in the marketplace and in venture capital fundraising. You and your husband, your co-founder Neil, are 13 years in this adventure. You've got a tremendous amount of lessons and most of

Caitlin MacGregor (04:07)
Yes.

Mark Cleveland (04:12)
the people involved in listening to Parallel Entrepreneur are super curious, they want to know about how you balance the work life. So let's go ahead and stick with that, you know, between your venture and your family. But they're also really interested in how do you balance growth capital from venture sources or from investors and, really growth from customers. So I'm curious about how you approach the balance in work life from a specific hack perspective, and then how you're approaching 13 years of capital raising experiences and growing a company through customers investing in your product.

Caitlin MacGregor (04:48)
Yeah. there's a lot in there. So let's, let's start with the fundraising just to give some high level numbers and then I can come back to it. So been doing this for 13 years and we've raised about $15 million US to date through several rounds. So when, when we started, it was completely bootstrap, no, no outside funding. And it was a really interesting time when we first started because,

Mark Cleveland (04:51)
Yeah.

Caitlin MacGregor (05:16)
as you said in the intro, I built two businesses for other people. At the second business, which was an ed tech company, my husband was the global expert in the software and he actually brought me into the company as the US president to scale up and run a Canadian business in, the US. And so we, we went to New Hampshire, to scale and grow this US branch together, him being the expert in the software and me being the, business, growth component of it. And we realized that, my superpower is building something from nothing. Like it doesn't matter what job I would have if it's building a company for somebody else or building a company for myself. Like no matter what I do, I'm going to be that entrepreneur through and through. And we had the experience of working on completely different initiatives where, you know, he was working nine to five, and, and training, teacher, students, and parents on how to use software for students with learning disabilities, how to be successful. But it was a very nine to five job. And then there was me building a business from scratch, the first business. It's really hard. I mean, anybody that's an entrepreneur, married to somebody who's not an entrepreneur, we know that it's hard to be on the same page. It's like we're driving at completely different speeds, and it's hard to be on the same page. So when we had the chance to work together, the relationship just worked better. The same speed, always there supporting each other and always understanding, you know, if there's a late night, you understand the context and the reason why and the payoff for it. Or, you know, if you need to support each other in different ways. So when we had three years of working together on somebody else's business, we really were determined that we wanted to start our own company. If we're to put in all this blood, sweat and tears might as well do it for ourselves. And at the same time we were ready to start our family. So I was literally two weeks overdue with our first kid. And, Neil came home from the office and said, I've got this idea of what we should do. And we were looking for an opportunity to start our own business and move back to Canada while we, while we grew our family. And so we, and I'll get into the founding story, but you know, we decided to start this business, together as this idea that, I'd be on maternity leave and we could just do this off the side of our desk, which I think was incredibly naive, but it allowed us to, while we still had paychecks, kind of start to validate our idea. And when our son was seven months old, we went and did this full time and moved in with my mom in small town, Southern Ontario, working out of my childhood bedroom with a seven month old. And so we started our family and our business at the exact same time, like two weeks apart. And so this whole journey has been one where we've not only had to think about how do we grow this business, but how do we grow our family at the same time and, you know, keep everything balanced and keep everything healthy. Anybody again, that's newly married, they know that newly married is hard. They know that like starting a family and having, you know, we had two kids under five is hard starting. And fundraising a business is hard. Like we did all the hard things at the exact same time, but we didn't have to, I never had to do it alone. And I remember our son was seven months old and we were literally driving, you know, three hours to Toronto to get entrepreneurial support. And our son was in those bucket seats that you could carry. And, know, we kind of put them underneath the table and

Mark Cleveland (08:20)
Woohoo!

Caitlin MacGregor (08:36)
have our business meeting and then drive three hours home with him in the back seat. Like when we had our second kid, I was on stage two months after he was born in a pitch competition to win $250,000 US and my husband was in the green room with the second kid, in a bucket seat while I'm on stage pitching. So part of this whole thing is just recognizing that, um, you're, it is help to have support along the way and to never really feel guilty. Like if he needs a late night and that means I'm on kid duty or, you know, dinner duty, then there's no resentment. If I need to fly to go somewhere for a week for work, there's no resentment because we're always helping each other. And, and along the way that's led to $15 million of, of fundraising through various rounds of funding from one and a half million of angel funding. And the great thing about angel investors is that a lot of those angel investors are investing like they're angel investors because they're investing their own money. Right. So they're looking for who's passionate, who's solving a problem that they care about. And a lot of those times, those angel investors also are investing with their spouse's money. So, you know, we have several couples that, husband and wife couples that are on our cap table from those early angel investors. So I'm really grateful that people kind of saw the potential and the strengths of what we had. But when we started raising from venture capital, like a lot of the times when I would go in, I wouldn't talk about my husband being my co-founder. He wasn't in the room. He, I wouldn't, I wouldn't mention it. Like I would never start a podcast if we were five years ago, eight years ago, admitting that my husband was our co-founder because I wanted, I didn't want the first thought out of their heads to be, oh, that would never work for me. I'd never be able to work with my wife. Cause that's most people's gut reaction. Like I'm wondering how many people that heard that in your intro, their immediate thought in their head was, I could never work with my spouse. And cause we don't see it as the pattern. We don't, we don't, we hear about, in Hollywood, all of the divorces and separation of assets and how messy it is. Like people know the statistics around divorce over 50%. They know that small businesses, the chance of failure are so high. So there's this internal fear that it's not going to work out. So there was a lot of bias that I had to handle where a lot of people, that was an immediate red flag. And it wasn't until we found investors that had invested in couples previously. And those were the winning ones. They, they didn't have the divorced co-founders that were complete strangers and had no loyalty to each other. So it's been this big journey of kind of going against the pattern and getting people to, see that there is a different way of doing things. And when I talked to other women that are CEOs, a lot of us are married to our co-founders and have had to deal with just not putting it front and center. And it's only now after years of success, success that I can kind of talk about it.

Mark Cleveland (11:35)
Yeah, you get insulated a little bit so you can dive into it authentically and really identify it as a superpower. And I'm interested in this idea that parallel entrepreneurship is really the unleashing of potential everywhere. And you have to stop accepting the external judgments and failures of other people who are not actually in your business making decisions. They may decide to invest. They may decide not to invest. They may get enchanted with the story. I really think that this is about not fitting the pattern. And the lessons from not fitting the pattern are so many. Let's dive into a little bit about what you learned about raising capital fast versus raising capital slow or not raising capital at all. Did you decide that there was a point in time when you're not going to bother?

Caitlin MacGregor (12:21)
Yeah. Part of the thing was that when I was raising, let's say eight years ago, there was this thought that you could just run out and do a three month process and you would end up with millions of dollars. And in every time that I've had to fundraise, it's always taken like 99 nos to get to the one yes. And unless you are starting day one with a Rolodex of a hundred people, you can't just run this process of, oh, I'm telling everybody that I'm starting and it's going to close in 60 days. Like it just, it doesn't work that way. I've realized that I've had to take a lot of time to grow that Rolodex. You know, most of our customers are in the US but because I'm in Canada, just my natural proximity, my network, was Canadian. And so if you look at where the money is if you are in San Francisco and you are having coffees every day with different people, you can grow that Rolodex really quickly through referrals. But if you aren't right in the heart of Silicon Valley, or you're not right in the heart of New York and you have all of those existing connections, there's a whole bunch of energy and time that it takes to build up that Rolodex and to have people vouch for you. If you're not known, and especially if you don't fit, fit the natural pattern, you know, you don't look like Mark Zuckerberg, you don't have Mark Zuckerberg's background. Then if you don't fit that pattern, then you have to have a lot of people that do fit that pattern to vouch for you, to give you that credibility, unless you have rocket ship numbers and your numbers just are already putting you in the top 5%. It's really hard to stand out from that crowd. So it's like any sales process. I've had to go through, like I said, 99 nos to get to the one yes. And so I have found it can take a year. It can take two years sometimes. It can take, you know, a year to get the first part, but then to get the second part another year, like it's always incredibly time consuming. And one of the things that has changed in the last two years is that the playbook for tech companies in terms of, raise a lot of money, grow at all costs, the name of the game is to grow exponentially. Um, this idea that Reid Hoffman put out of Blitzscaling, where by spending $1, you're making an investor $2. Y Combinator had this whole playbook of exactly how to fundraise and how to run this process and all the do's and don'ts of how to, how to fundraise. I personally think a lot of that's gone out of the window in the last two years because the valuations have changed, the access to capital has changed, the market is changed. And so a lot of the, a lot of that playbook for fundraising, I really now in hindsight, second guess if we should really be telling entrepreneurs moving forward that that's, that's the game that they should be playing because so much of that climate has changed.

Mark Cleveland (15:01)
Yeah, it has a lot to do with your why. Why are you in it? Why are you raising money? Why are you a top 5% company? How is that being expressed by your customers in more business and success? I read a book. I'll ask you a little bit later what books are you reading right now and what's on your nightstand, because it's one of my favorite questions. But one that was on my nightstand speaking directly to what you just mentioned was - I went to Chicago and I went to a Bo Burlingham conference. It was the Small Giants Conference and it was spectacular. It's the first time Bo Burlingham wrote this book, Small Giants, Companies That Choose to Be Great Instead of Big. And at the time I was running Swiftwick, American sock manufacturing company doing everything differently than everybody, and a company called Hobby Lobby that was radio controlled airplanes, cars and trucks like they have - there is no, no similarities between those businesses. And I was having a ball in both of them, but I got this pressure from investors or from myself probably to scale Swiftwick. And, and then I went to this conference and I got permission really for the first time that I didn't have to scale for scale's sake, the purpose of this business and the people that were around me engaging and trying to help me grow it and teaching me how to grow it. We could just be the world's best in our small category and be a giant and own that category and just not try to be Under Armour. That was super empowering for me. I'm hearing you talk about this similar lesson for you.

Caitlin MacGregor (16:35)
There definitely has been an understanding that I think that there's a lot of pressures that we get of what success looks like. Part of being, for example, part of the Entrepreneurial Winning Women through EY, we're a class of 20 women. And so I was in a room with 19 other women, only four of us from Canada, the rest from the US and a lot of those businesses were, their sales were quadruple what mine are, or if not significantly more, but some of them have never raised money. And when they hear how much money I've raised in their eyes, I'm so successful. But for me, I'm like, you know what? If I didn't spend that year going through the 99 nos to get the one yes each time I fundraised, like I'm talking in the 13 year journey, there's probably a good four years straight of fundraising if you add it all up, you know. If I had taken that time to be becoming the best instead of at fundraising, but the best at sales, like I was, I really saw myself as an operational CEO. I'm somebody that can come in and put the maturity of how to grow the company and, have a really healthy company through and through from, from everything from finances, all to your people practices, to your operations, to your goal setting, to the alignment of the company. Like I was an operational CEO, but I didn't know how to be a sales CEO. And it's taken me working - you interviewed Jason Putnam, who's our chief revenue officer - he has taught me how to become a sales CEO. And I just think about if I had taken all of that energy in fundraising and learned how to sell, and I mentor a couple of startup CEOs. And the thing is, as CEOs, we always gravitate towards the thing that we have strengths in. And so I let other people sell. And what I have seen with the most successful businesses when it comes to growing revenue is the CEO knows how to sell their business. You know, they may not be the only one, but they know how to sell and I feel like it was a mistake -all the mentoring and all the courses and all of the, the tech playbook that was jammed down my throat was all about fundraising. And that's what I got really good at. And I just think that not only has the environment completely changed, but we need to be encouraging every CEO that sales should be the thing that they're spending the majority of their time on until they truly have product market fit where it's rinse and repeat. But as we learned, at least in my industry last year in 2024, the market changed, like the market conditions changed. And so it means that you have to find product market fit again. And so the CEO is the best person to find that product market fit because they can iterate until things go, back, back perfectly fitting. And so like I, fundraising was not easy. There was a whole bunch of pattern matching that I did not fit. But I persevered and I found that yes. You know, I kept going until I found the yes. And I kept, you know, developing those networks until I found people that were aligned to what I was doing. And I'm very lucky that I succeeded, but honestly, my biggest advice to entrepreneurs is it's not about fundraising. It's about growing your business through customer sales. And it's better, better muscle to build than learning to play the fundraising game. And frankly, you should only be fundraising if

Mark Cleveland (19:52)
Which might be interesting because you can bring a company into the top 5% through execution. And I've heard you say, I've heard you use the word healthy so often so far in our conversations. And I love the focus on that. I wonder, I don't think that you're unique in that approach, but does the feminine approach to leadership tend to make you focus on that word and on that metric as a part of how you view things?

Caitlin MacGregor (19:58)
That is a really great question. I've said it kind of like that, but never been asked it like that. So let me just take a second. I mean, it's a great question. So there was a definitive moment in two definitive moments in my journey. One was that the second business I was building right before Plum, I was newly married and I was working around the clock. I would go to work at nine 30 and I wouldn't come home until 10 all the time. And it was the age where the CrackBerry was out. So Blackberry, you know, work just never, you were always, always, always accessible. And it was kind of the first generation of that. And I was newly married and, and I came home and we had a best friend that lived in our apartment building who had been a dotcom boom bust entrepreneur and had left the entrepreneurial world. And he said to me, Caitlin, if you keep going where you're never home, you won't have a marriage to come home to. I was 27, he kind of said like, you're having lots of success being an entrepreneur and building a business from scratch. Um, but it's coming at a huge cost. And if you're already having this cost this early, year one of your marriage, you won't have anything to come back to. So I started seeing an executive coach and the executive coach said that I was too agreeable. I was constantly saying yes. And by constantly saying yes, I was becoming a martyr. So if I got hit by a bus, whole business would fall apart and that was very empowering, but not healthy for me, not healthy for the business. I needed to learn to say no for everybody's benefit. And so I started seeing an executive coach and that was helpful. But then years later, I started seeing another executive coach who was in Silicon Valley, but he was originally based from Germany and he just had a completely different approach. And his idea of being a successful leader was that you needed to lead from a place of loving care. And he kept saying like a true leader, the best leaders, Caitlin lead from a place of loving care. And I felt this massive disconnect and frustration because in my home life as a wife and a mother and a daughter and a sister and a best friend, I was incredibly loving and caring. I very much felt like I was supportive of everybody at home through loving care. But when I came into the office, it's like I left that entire part of me that loves and cares at the doorstep of my home. And I come into the office and I'd be so transactional. I would just care about getting the things on my to-do list done. And I was so focused like blinders on to get the to-do list done and to overachieve and to over execute. That there was, I just didn't have the loving care and I, and it was so frustrating feeling like I was these two people and that I was failing as a leader because I, I couldn't access that other part. And I spent a year really integrating these two parts of myself. And it was all these feminine characteristics and men can be feminine too, but like these feminine characteristics that I had in my home life that had never been modeled to me

Mark Cleveland (23:13)
Mmm.

Caitlin MacGregor (23:25)
in the work life. And so I had no kind of role models as to what that looks like to figure out how to authentically, you know, become whole and to take these strengths in my home life and build them into how I was, how I could be as a leader. And I would say, Brene Brown is a great example. You talk about books. Like, I really think she is a great example of modern leadership styles and how we have to model. Like, you know, I model to my employees

Mark Cleveland (23:43)
Right.

Caitlin MacGregor (23:53)
all the time that if they need something and they need support, they need to ask for it. So how can I model that unless I'm being clear when I need support and what's going on in my life and that it's okay, you know, that I need to go and do X, Y, and Z for my kids. And, I have to miss that meeting. Can we reschedule it? If they need to do the same and I'm like, it's okay. Like they need to see me modeling the same, the same thing that I expect from them. So it took me a long time. It wasn't easy. But there was this point where I learned to integrate that feminine side of me into how I was a leader at work and learned how to lead from a place of loving care and supportiveness. And that made me realize that yeah, having employees that love where they work, like we have to drink our own champagne. So Plum is about, you know, if people flourish, then business thrives. I've got to create an environment where my employees are flourishing. I need to be flourishing. We have to drink our own champagne if we're going to demonstrate that our product works and that customers should be buying this. Like we have to do it first. So I eventually figured out how to integrate those two through executive coaching. And that's where it's recognizing what does success look like. And it's that happiness. Can - Are our employees happy? Is the business doing well as a result? What is needed? And a lot of the times that old model of, you know, I'm the boss, here's a paycheck. Your job is to shut up and come to work and do what you're told. Like that model is dead and companies that are still trying to run that model, they have employees that are just dialing in the paycheck. They're not really engaged. They're not really producing high quality work because they know that the employer doesn't care about them. So why should they care about the company? Like, yeah. So of, you need the healthy relationship and this healthy, supportive commitment relationship from both sides. If you're going to expect to drive success in your business.

Mark Cleveland (25:55)
So I want to get to this because I think there's a mindfulness practice in there as well. It's not just executive coaching and it's not just modeling. Both of those are important, but there's at least in my experience, there is that time that you need in order to integrate those lessons and gain a perspective on them. And at least for me, it's been mindfulness practices intentionally. Where do you sit with that?

Caitlin MacGregor (26:19)
I I believe that everybody has a different learning style. And so for me, being able to have an executive coach once a week or every other week to kind of hold that accountability. Like I think about it. If you're trying to weight train, which I just started doing this fall, finally, you can go to the gym and you can use the equipment incorrectly and you can see results eventually, or you can get a personal trainer and you're going to get to hit your goals much faster. So I'm a big believer in executive coaches because they give you that accountability and they, they help you get to the right answer faster. So, and for me, it's a lot of being able to talk through different situations and getting that course correction. So for me, it's about actively kind of practicing and conditioning and growing that muscle, that an executive coach has helped me with. And that's just kind of my style. I also learn a lot from peers. So being part of different CEO round tables and being able to hear from others, experiences and learn from others, has also been something that just works really well with my personal learning style. But there are things where I'm still growing. So, I've realized as I've gotten older, my stress tolerance is actually going down and it's related to my age. I'm early forties - for the women that are early forties, we all know that our hormones are changing. And so the cortisol is hitting me differently than it used to. So now I'm having to develop coping strategies that I never needed before. Like I've been an entrepreneur kind of my entire career, 13 years doing it on my own, but now all of a sudden risk feels harder to take to some extent. And so now I'm doing like the weight training, which helps I'm more like making sure I'm taking all the right vitamins so I'm not deficient in vitamin D that impacts a whole bunch of things. So I've been very conscious. And then the other thing is I am now starting to build in meditation, which is really helping with part of being comfortable with uncertainty. A big part of meditation is being able to let go and know that the answer to uncertainty, isn't certainty. It's kind of leaning into the uncertainty. And so I am starting to do meditation to help with that. And I found that it's really helpful, especially before big meetings. I was back to back today, but normally I'll do it before a podcast so that I'm less wordy than I am right today. I apologize to your audience.

Mark Cleveland (28:38)
Oh my, I need to, need to meditate so I don't talk myself, you know, don't worry about it.

Caitlin MacGregor (28:43)
But so I have found that, I'm committed to being a lifelong learner. just, I, it's for me, I need to see growth and progress and be better than I was the year before. And I haven't done meditation, but it's the thing that I've been, you know, starting to dabble in and I'm committing to get better at. So I do believe that these all play a role, but it starts with A, what are our learning styles? And then B, Are they stage appropriate? Like I, some of this stuff I didn't need three years ago, but I really need now. And so I have to force myself to say, you know, what got me here, isn't going to be what's going to get me there. And I think we know that early in our careers, but I think we need to keep ourselves to say is everything that we're doing exactly the same pattern we want to keep going for the next three or five years of our lives. And I think we were talking, you know, GenAI a great example. It changes so much. There's an opportunity for us to rechallenge all of our assumptions, the fundraising. I'm rechallenging those assumptions, you know, how you scale. I'm rechallenging those assumptions, how I handle stress. I'm rechallenging those assumptions because my biology and my hormonal balance is changing. So it's like really committing to, I think that self-awareness. I think the thing when you were talking about mindfulness for me, it's like, am I truly self aware and am I doing the right things to kind of create that proper balance where everything in my life is optimized?

Mark Cleveland (30:10)
So I love the Plum story. People who care to research it should go out there and research it. We're not focusing on Plum as much as we're focusing on people. And my experience with Plum, however, is that I'm watching you speak about it, the diversity in leadership, the balance and the health, the diversity in the employment group and how you bring people in. You're modeling that internally as an organization, and that is your product. You're helping companies take the blinders off in how they bring talent into the organization, how they fit that talent into this mission, how they get them engaged. Right. And so speak to the lessons of the joy and celebration and the growth opportunity that real diversity represents in business today. I mean,

Caitlin MacGregor (31:00)
I mean, this is, you said at the intro, this is the stuff that it's really hard to kind of understand. Some people have a really good gut instinct and they look at somebody and they can see their potential. I'm not one of those people. I just don't instantly, you know, see all of the potential of somebody. I'm easily persuaded. You know, we know that in interviews, people that are more outgoing and more assertive tend to perform better. I'm the type of person that if you come in and you say that you're amazing, I would probably believe you. And so one of the kind of the lessons with all of this is just recognizing that most people aren't self-aware as individuals. The things that make them exceptional we often as individuals take for granted. If it comes easily to me, how, how am I better than everybody else? If it comes so easily. So there's this, this gap between, you know, most people don't even recognize what makes them exceptional from their peers. And then when we get into having to represent ourselves to others, the ones that end up getting the most promotions or getting the most hires are these, these acts, you know acting, you know, really outgoing or acting really assertive. And so there's a lot of people, they get looked over. So the, the kind of point of all of this is through my journey, one of the biggest lessons that I've learned is that there's a science behind all of this. There's a science to putting on those pair of glasses to actually understand what makes somebody exceptional. And when you can identify what really drives a person, either as the individual or as the employer that's hiring them or promoting them, when you can understand what is unique about somebody and what drives them and gives them the sense of self-worth and that allows them to outperform their peers and what will bring them joy and happiness, so they'll be loyal and they'll go above and beyond. When you can understand what drives somebody, we have a way of optimizing our workforce in a way that just could never compare to a gut instinct. And it really is amazing because when you can put somebody in a role where let's say you need an out of the box thinker. So let's say you're starting a business and you could hire somebody with 15 years of marketing experience.

And they're really expensive and they've done it using these old methodologies, or you can hire somebody, for example, that's either didn't do marketing. They did something else and they're new to it, or they're coming into it early in their career. They're like a clean slate. Well, that person who's a clean slate may be able to go and adopt some of these GenAI marketing tools faster than somebody else, cause they're that clean slate. The difference is, that, do you need an out of the box thinker? Okay. Forget about past experience. Forget about if they have a clean slate or if they have tons of experience, who's going to naturally show up to every situation and think outside the box and say, how can I do this differently versus the person who wants a really formal process and they're very project oriented and very much about every detail and executing on every detail.

Mark Cleveland (33:41)
you

Caitlin MacGregor (34:04)
Every single piece of data says that if you're looking at performance and retention, it's about the behaviors that make somebody exceptional and are those the behaviors that you need for success in the role? And there's data around this and that data helps somebody be more self-aware and help them navigate their career and help them develop. And that same data can help an employer get through all of the automated resumes that are being submitted right now. And, actually understand the human behind the work and understand how to optimize them. And so it's been kind of amazing to have this data and then to kind of find these diamonds in the rough and put people into these roles where they're just, you know, no one else would have ever thought that they would excel in this role. But because you have this data on how there's such a strong behavioral fit, you now can see a whole new career path unlock for them and a whole new journey where they are happy, fulfilled and they're contributing at an exponential rate to a company.

Mark Cleveland (35:01)
You know, you mentioned earlier about the CEO, a challenge for you and a challenge for CEOs that you are familiar with, that they're maybe not sales oriented enough. And I wonder if that's really customer oriented enough. And I'm asking that question because you use the word iteration. You know, they could iterate faster. They could adjust in a changing market so that pattern matching - when the markets changes, your patterns are out the window. Now what? You know, and I think it's it seems to always rest on the shoulder of the CEO. But what happened? What would happen? What's the possibility if your entire organization was was filled with the job function that needs to be done, the behavioral pattern and skill sets that can make that job sing and that person sing. The market changes, but your whole organization is capable of iterating and rediscovering and learning. It sounds to me like, like a human biology expressed in the form of a business.

Caitlin MacGregor (36:04)
Absolutely. And I mean, to be clear, it really comes down to what stage you're at. I think wishing that I was a "Sales CEO" would have been far more beneficial in the early days when I was busy building the business, you know, like I'll, I'll meet with some of the, one of the two founders that I mentor right now, you know, they'll come and talk about all the KPIs that they've hit, but they're not revenue KPIs. They're like,

Mark Cleveland (36:14)
Huh.

Caitlin MacGregor (36:26)
We released this or we, you we built that, or we, you know, had this product feature, for example, and it'd be like, okay, so you feel like you're growing something because you're building it, but what, what revenue did you hit? So some of that is, I think earlier stage when you're, when you're bigger and you can start to delegate, like you can start to have other experts on the team a hundred percent. The question is, can you optimize for every role? Do you have the best person for the best role? And then, do you have a high level of trust between the different people so that there is that collaboration? Like that's the other thing kind of with leading from a place of love and cares, you know, recognizing that everyone's bringing different strengths to the table. And so you need to have this trust that, Hey, I'm going to work as hard as I can on the things that I'm working on, but I'm also there to support you. And if you need my support, then you have it. And I'm not going to, we're not going to point fingers at each other because we know that we're all doing our absolute best towards the same common goal. And we're to take the time to learn about what each other's doing. And we're going to learn how we can support each other. And we're going to take that time to, you know, not be a silo, not be siloed, but be more organic in, the ways that we come together to utilize our, our diverse strengths to support each other. And that alignment and collaboration has been a big part of the journey, but it starts with, do we have everybody in the right role to begin with. And if you have that trust, then you can just run faster together.

Mark Cleveland (37:53)
I love as for those of our listeners who are not watching on the YouTube channel, when you start talking about love and support and trust, you're just leaning into your microphone. I mean, all of a sudden you come alive and you're you're leaning forward in the conversation. We we often, at least in my experience as an entrepreneur, I have been striving for perfection. Just just can I outperform for the performance sake of performance? Right. And perfection ultimately, as I've aged a bit and I've become a finer wine, I hope, I've learned that just creation is the thing and create and release, iterate. Lean into the discovery process and the uncertainty because you can't press, certainty is no fun. Certainty, in fact, certainty, at least in my experience does tend to make me unopened to other perspectives. So talk about the balance of striving for perfection, both as a family leader in a family and a wife and a leader in the organization and now a leader in your community. The Ernst & Young Entrepreneurial Winning Women of North America. Tell me about this battle that I'm assuming you have because I think we all have it between perfection and creation.

Caitlin MacGregor (39:13)
I think you nailed it in that, you know, it's what I've seen with perfection consistently is that perfection requires control. And so it ends up being a single person or a single team that says, we're going to go and do this thing and we're going to control every element of it. And we're going to go off and do it on our own. And that doesn't leave room for collaboration. It doesn't leave room for doing things differently. It doesn't bring in other expertise. It doesn't allow for that gray space of figuring things out. and so I have just seeing that it, it doesn't, the only person that serves as the person that gets to say, see, I hit this KPI all by myself and pat on the back. But what happens if it took too much budget or took too many resources away from other parts in the organization? Like as an organization, you need to succeed as a whole. And so the question should be, what are we trying to achieve as a whole company first? And does that require collaboration in order to create the best outcome? And if so, collaboration is uncomfortable because you don't get to, you don't get to control everything outside of your department. You don't get to control all of the elements. So you have to be open to other people coming into that solutioning. But what I see when you have that kind of alignment, when you, when I see that kind of collaboration, I see

Mark Cleveland (40:15)
Thank

Caitlin MacGregor (40:37)
much better results, much better approaches, ones where we're balancing the resources, not at the cost of something else that could have been equally as important. One of the things that I did kind of in as an outcome of this executive coaching is I ended up taking this professional development course called the Collaborative Operating System. And was more about just teaching the importance of why you should collaborate. Why, why collaborate when you can just go off and create this perfect result on your own or with a small team that you can control. And so it took a long time to understand the, value of getting buy-in and that sense of shared ownership and how you just, you have more people that come along and more power behind what you're doing because you have the collective involved in doing it. And so it took a long time to understand why to even choose collaboration over other solutions. But as a result of that, I ended up designing a unique, our own system for creating goals and creating KPIs. I really didn't. Yeah. So I call it the collaborative operating, the Collaborative Operating System or the company COS. So think about your operating system on your phone. So what's that? That's COS company operating system for, for your own company. And we start with what are we trying to achieve as a company first?

Mark Cleveland (41:37)
Let's dive into that.

Caitlin MacGregor (41:55)
And, you know, annually, and then how do you break that in down to, okay, this quarter of that annual goal? What are we going to accomplish? And the executive team is responsible for accomplishing whatever full goals as a company we agreed to, which means you don't have a goal for the revenue team. You don't have a goal for the product team. You don't have a goal for the engineering team, a goal for the finance team. We collectively as an executive team say, what are we as a company trying to accomplish? And ideally that's something that requires lots of us to input on, like if we have a partnership strategy, okay, well, how is all of the different departments, how is finance contributing to a better partnership strategy? How is product needing to think about how they can increase that product strategy by 10 %? is engineering, like, how do we align all of our resources towards these, you know, three to five goals that are so important and critical for the business to progress? And it just is such a different way of thinking about it then, okay, what's the head of marketing going to go off and do and succeed with and what's the head of engineering going to go off and succeed in? Because you can have every department leader hit their goals. And the company run out of resources or energy or budget to accomplish any of them successfully. So, or sustain them, but it's super uncomfortable because you no longer have full control of that goal. You have to work with others.

Mark Cleveland (43:11)
Or sustain them.

Caitlin MacGregor (43:20)
And the trade-offs of resources, time, budget, money, but it's so rewarding because you're not alone either. You're getting that, that buy-in. And then this goes back to people and their strengths. The idea is if you've got some people that are great at thinking outside the box that are great at innovation, and you've got some great people that are great at persuasion. You've got other people that are great at working on teams. You've got other people that are great at communication. The idea is that when we have to communicate the plan to the company, I know who's the best at communication that I'm going to lean into to help me communicate that strategy. If I need to figure out how two departments are going to work together in a brand new way, I know to lean into the person who's strongest in teamwork to make that happen. And I'm not going to get mad at the person who's really, really strong at teamwork for not coming up with a better out of the box idea. I'm going to lean on the innovation people. So part of it is in order to collaborate, it's that trust that you know that people are bringing the best version of themselves to that project, but they're being utilized effectively. And so it gets away from the finger pointing, cause you know, nobody's sitting back and going, well, this isn't my responsibility or, know, I don't care about this or I'm just going to dial it in because the person who comes up with out of box ideas, they're going to love the opportunity to innovate. The person who loves to build bridges with other teams is going to love doing that. They're going to be invested in their job because they have a sense of self-worth at the end of the day because of it.

Mark Cleveland (44:46)
How you, you're describing the behaviors and the outcomes, I think, of a company that does not suffer from politics. How do you, is this how you eliminate politics in an organization?

Caitlin MacGregor (44:58)
I mean, I think that again, like what's the main goal of the company? I think before it was grow at all costs or, or profits. And there was a contract in with employees. Here's your paycheck, check, show up and do your work. And, you know, here's a 401k. We, we now are doing 401ks because we have to be competitive with other companies. So now we're providing it as a bare minimum, but this contract with "do the work no matter what" with an employee. I just don't think that that works anymore. I think that employees want to work for companies that give a shit about them, that have that symbiotic relationship. So when it's truly about how do we ensure that every single person can bring, what drives them into their job and, gives them that sense of self-worth and allows them to flourish - when we actually care about setting people up for success, they enjoy their work better. They perform better. They stay longer. All these things that companies need. But there's this thing of companies are worried that, if I support my worker too much, they're going to take advantage. If I care about this person too much, they're going to take advantage. Instead of no, if you actually started caring about them, they may care about you and actually do their job with this incredible output. We have to change the relationship to the best of our ability. I mean, there are still financial constraints that are still constraints that, there have been times in the past where I've had to let really amazing people go, it had nothing to do with them. There are constraints in the market. Spend has to change, things like that. There are always going to be constraints, but I think if the idea is we want to maximize the output of the company by maximizing the output of our employees. And the way to maximize the output of our employees is to actually set them up for success. Then the politics go away because everybody's aligned to a much better outcome that benefits everybody along the way, where it's not about taking advantage of people and expecting that they're just going to be okay being taken advantage of.

Mark Cleveland (46:57)
A common... So your life must have had a failure involved, a spectacular failure, a fail fast, a fail forward. Whatever the sort of term of the day is, I like to call it a spectacular failure because it's a spectacular opportunity to learn. Talk to me a little bit about your spectacular failures.

Caitlin MacGregor (47:24)
So this probably isn't fair, but I'm going to throw this one in here just because people might be, be wondering, the, the failure was the spark for starting Plum. So I, I built these two businesses for other people. I can tell you in the prior business, lots of failed hires, lots of like people that look great on paper, didn't work out people that, you spend a year hoping that they're going to be the kind of succession plan didn't work out. So I'd seen kind of the cost of bad hires, but when Neil and I went to, um, New Hampshire to start up the, the US branch of this Canadian ed tech company, our executive coach at the time said that if we screwed up that first hire, it'd be a loss of $300,000 on the business. So, my jaw dropped being like day, day one of being president of this, of this US branch. I don't want to screw that up. I don't want to lose $300,000 from a bad hire. And I'd seen firsthand how realistic that is to do. So we, we ran an experiment. We used a psychometric assessment, a personality cognitive assessment on all 80 applicants that applied for the job. And, two candidates stood out for different reasons. One was perfect on paper. He had a master's in education, five years of relevant work experience. He was the golden boy by every measure. My CEO back in Canada was like, this is the perfect guy. You've got to hire him. We're so lucky. Really expensive salary, like all of it. But the assessment showed that he had a mediocre work ethic. He was hired anyway. Then we had somebody else who out of all 80 applicants was the highest scoring applicant, she was in the top third percentile of the workforce for overall productivity. And my executive coach said, you'd be an idiot not to hire her. She's one in a thousand statistically in terms of how likely she is to work out. So we got permission. We ran an experiment, hired the guy who had was perfect on paper and the woman who had the highest assessment scores. Well, three months later, the guy's fancy football team was doing really well, but he was only doing 10% of his work. The woman on the other hand was doing all of his work plus hers. And within a year and a half had replaced me as acting president while I went on maternity leave and the punchline is she had two art degrees. Her only work experience was seven years of waitressing and she didn't even know how to use Excel. So if I had relied on a resume, there's no way I would have interviewed her, let alone hired her. And that was the case for the next three years. We kept finding these incredible diamonds in the rough by looking at the behavioral and cognitive data for each person and how well it aligned to the role. And that's where I realized that there's no way that I could ever be successful as a CEO, either running my business or running somebody else's unless I had this data on everyone. And I saw in the market that to access this highly predictive data and this, you know, field of industrial organizational psychology, that's a proven science, it was really expensive and really hard to access and a horrible user experience. So we started Plum to create data that people could have on their own, like a LinkedIn profile, but not based on what they've done historically, but based on what they could do, if given the opportunity that benefited the individual first. So they would want to take their Plum profile and then, you know, to have this data be intuitive so that you could scale it without having to have it interpret with a decoder ring by a really expensive, you know, IO psychologists, industrial organizational psychologists. So, I think it was the, the expense of failure that really showed me that there was another way and inspired me to, to build Plum. And, and now, you know, I keep going because my 13 and nine year old boys, like when they grow up, I don't care if they're doctors, lawyers, teachers, nurses, I just want them to be happy, fulfilled and thrive in whatever career they, they find. And when I look out at the landscape right now, there isn't something that can tell them where they would truly flourish except for Plum. And so we keep going so that we want to be able to match every single person to every role where they'd be happy, fulfilled and flourish.

Mark Cleveland (51:22)
So would that be your advice to your younger self? Go find a place where you'll be happy, fulfilled and flourish and don't let anything stop you until you get there.

Caitlin MacGregor (51:31)
Absolutely. And I'm really lucky because my very first boss, he saw that potential in me. But I think about if he had not seen that potential in me and given me the opportunity. I mean, I was hired to build a business from scratch and I had never done it before. I had no experience in that industry. I knew nothing, but he saw potential in me and just got out of my way and let me build something from nothing. But if I had not met him, if that had not happened, I don't know if I would be here. So, you know, I really wanted to start Plum to democratize access to that type of experience, because if we've been fortunate enough to have those people in our lives, that's great. But most people, they don't, they don't have that person that sees that potential and has the resources to just align them to a limitless career. And that's why a lot of time entrepreneurs, they invest in their own potential and they go out and create their own, because nobody else would give them that opportunity, which is great, but ... Every single person has that path where they could be fully optimized and it shouldn't come down to luck and chance that somebody sees that in them. We've got data and software in 2025 that can allow that to happen for everybody.

Mark Cleveland (52:42)
So one of my superpowers that I've, as I sit with this parallel entrepreneur concept and try to distill and pull out from other parallel entrepreneurs, what makes us successful and tick. I've gone into lots of different industries, like literally started a new company in an industry that I know absolutely nothing about. And I'm not, this conversation is distilling a little bit about why that might work. Because I know what to do and how to do it. And I don't know anything about the short sea shipping business, not a thing, or the bicycle manufacturing business or the sock business. And it never scared me to go in and do something I knew absolutely nothing about because I figured I knew how to build an organization and treat people and work with customers and do ethical behaviors. So, I'm really getting a charge out of this part of the conversation where you're just saying, and guess what? There's a whole lot of other people out there just like you, Mark, and you could organize your business around finding people like that. And how, how magic, how much magic could we set free in more than one business that we, we, we might look at and, you know, say grace over in some way, but really we're just trying to get out of people's way.

Caitlin MacGregor (53:58)
And that's, that's the magic of this, especially if we look at how hiring's happening in 2025, where, job applicants can apply to 5,000 jobs in their sleep using a product like Lazy Apply. It is a lose-lose situation right now where it's bot against bot to try to get a job. And it all comes down to keywords and a resume. And the reality is, is that it doesn't really matter in many, many ways. It doesn't matter what you did in the past. The past is no longer a good

Mark Cleveland (54:19)
Thank.

Caitlin MacGregor (54:27)
determinant of how somebody is going to perform in the future. That time to learn on the job is so short. It's so easy for people to be up skilled. Now we have a customer where they train people in cybersecurity in four months and there's 3.5 million unfilled cybersecurity roles in the world. So we need to train more cybersecurity people. The question is, is, is that person going to be exceptional once they've learned it? You can't teach the behaviors, that ability that you were talking about - it's transferable.
And this is the, this is the time where we need to really double down on people's transferable, durable skills, those skills that are going to consistently survive and be useful throughout their career and allow them to learn the rest, allow them to learn the hard skills on the job, but really invest in that potential. And yes, you can have an entire team. And I can tell you those people are less expensive because you're betting on them when nobody else would. And they are so loyal. They're excited to stay with you and to grow and be part of that journey because you bet on them. So they're going to bet on your company too. And so it really is a differentiator to access pool of talent that your competition is not accessing and to get that higher performance and to get that increased retention.

Mark Cleveland (55:38)
So there's probably a question that I know you to be somebody who's highly prepared. You're always well prepared. So tell me the question and I'm imagining go ahead and answer the question that I didn't ask you that you thought I would.

Caitlin MacGregor (55:53)
What book am I reading right now? Okay.

Mark Cleveland (55:55)
Well, I already told you that one. Well, yeah. What is the question you sort of, said I'm going into the Parallel Entrepreneur podcast. Mark's going to ask me some questions, which, which one should I have asked and I didn't, and which one did you have an answer for that? I didn't answer.

Caitlin MacGregor (56:11)
Oh my goodness. I mean, the one that I just think everybody needs to talk more about it, and I've been hinting to it is just the impact of GenAI. I mean, we're not we're not going to have robots taking our jobs, we're going to have robots taking the tasks. But that really asks like how, because that contract is going to look differently between employer and employee, like -

Mark Cleveland (56:14)
No.

Caitlin MacGregor (56:35)
are we really understanding how we could do things just entirely differently than before? Like really challenging our assumptions. And that's where I think, you know, seeing employees truly as potential that we can leverage in brand new ways, because we're not just repeating what we've done historically, we're building businesses entirely different ways and, and, and they can look very different than before. And I mean, listen, if you're a brick and mortar business, like I'm not, not necessarily what I'm talking about, but - there's so many businesses where we can reinvent a lot of the tasks that we were doing historically and we can do them more efficiently than before. And so how do we really understand that there's an opportunity to do things differently? One of the best examples that I heard, and it's a bit long to explain, but I'll try to do it quickly, is when electricity first came into the market in the early 1900s, they actually didn't make more money than steam run warehouses. And it wasn't until they had about 10 years of doing electricity that they realized all the cost savings that they didn't need to put in these metal beams. They didn't need to put in these two story buildings. They could start building their buildings completely differently when they fully embraced electricity. And then there were tons of cost savings and tons of incremental savings by doing things differently, but right out of the gate, there wasn't a tangible cost difference from a steam powered facility versus an electrical facility. And I think we're at that with AI right now. I think that GenAI, you know, the, the value of, of running a business using some of these GenAI tools versus how you've been doing things for the last 10 years, it's not super obvious right this second, but getting going - starting to build your building from the ground up differently with GenAI, that there's going to be exponential savings and how we think about our employees and the time to learn and the value and the relationship and the things that are uniquely human. I think there's an opportunity to do it differently. And I think the companies that get started now are going to be way ahead of others that are just going to be in a position to follow. I think we've got to figure out a bunch of things differently and you know, hiring people based on potential versus past experience is just a small example of an opportunity to do things differently. Especially as parallel entrepreneurs, we can be at the forefront of experimentation and seeing how we can do business differently.

Mark Cleveland (58:59)
I love it. The book that you're reading right now?

Caitlin MacGregor (59:01)
So it's by my fellow EY Entrepreneurial Winning Women, class of 2024 colleague. So it's Kara Smith Brown and it's called The Revenue Engine. And she's amazing at really talking about that marketing funnel and how to think about it differently and really think about the metrics around it differently and to make it very quantifiable and leveraging a lot of new tools. And so it's a really practical book and I'm really enjoying it.

Mark Cleveland (59:34)
And what's on your nightstand? What's next?

Caitlin MacGregor (59:37)
My nightstand is fantasy romance, to be honest, is total escapism. It's to completely, so for the most likely women, the third book in The Fourth Wing just came out today. So when I'm done the series I'm reading, I will be reading Onyx Storm. So there's the vulnerable personal side of it.

Mark Cleveland (1:00:00)
So what's your relationship to art? How do you view the art of business being the canvas versus the art of other forms of art? And I don't necessarily mean to put them one opposed to the other. I'm trying to make them a complimentary. How do you see art in your life?

Caitlin MacGregor (1:00:19)
Good question. Okay. So in personality, if you, you look at it, there's a specific part of like the big five that's called openness to new experience. And a lot of people that are very creative have very high openness. And in the early days when we use very technical language, now it's like innovation. It's very intuitive, but back in the days, like rewind, like 10 years, we talked about something where it was like experiential disposition and intellectual disposition. So some people that are really high in intellectual disposition, are constantly learning. Like they probably kept going back to university or they would love as an adult to go back to university. Like they love to just keep learning. Like on the weekend, they'll be going down rabbit holes of just learning about, I don't know, black holes or the latest LLM or, you know, they'll just learn, learn, learn through absorbing content. And then there's another one, which is experimental disposition, is experiences. So art for me is experiences. So art is trying new foods. It's going to new countries. It's learning about new cultures. Like it's not a piece of art on, on the background like you have for me, what excites me and fills my bucket is trying new things that have never been done and learning through those, through those experiences. And so - I lived in Ghana for a year. I lived in France for a year. I lived in China teaching English for a year, all when I was younger. And that was just the most amazing experience to constantly my entire environment was a form of art. And I, it's one of those things that like before, before starting the company, before Plum, my husband and I took three and a half months and we, we traveled around Asia, went back to places like Thailand that we had seen when we, uh, taught English in China after university, but like, that's the thing now that I think I miss the most is that I really want to take my kids to Thailand for a month. Um, but I like it's, it's on the horizon. It's a, but like, it's, it's, it's a big financial commitment. It's a big time commitment. It's a big thing to carve out, to prioritize. And I'm getting closer and closer, but I'm just not quite there that I can prioritize that over all other things, but like, I have this hunger to not only go back to Thailand and have that all of that art, but to to have to now share it with my kids, to have them have that enrichment. Like I'm more excited about having to share some of this with them. Um, like I never thought I would like helping my kids with homework, but I'm actually loving when I get to share something that I know

Mark Cleveland (1:02:43)
Mm-hmm.

Caitlin MacGregor (1:02:59)
with them or figuring it out. I'm using chat GPT to help me tutor my son in math, which is like a whole new experience. Like it's not hard. Chat GPT tells me exactly how to do it. Like that's, that is really cool and a new learning experience. So to me, that's, that's, think where my evolution and how I personalized that, question.

Mark Cleveland (1:03:20)
So when we're putting together the dots as leaders, parents, humans interacting with other humans, think we wind up my algorithm is a pattern matching, expansive perspective. And part of that, I've been to China, I've done business all over the world. Well, actually, I'm about ready to plan a trip to Thailand. So after this conversation, let's have that conversation. But I'm curious, what do you see next? I I'm constantly looking for the next thing. It might be the next business. Where do you see opportunity just sitting on the floor and you just can't believe people aren't picking it up and running with it?

Caitlin MacGregor (1:03:57)
The thing that excites me the most is transformation work. So, I mean, I saw three years ago a lot of enterprise companies were like, I'm just going to buy a bunch of technology. I'm going to automate everything. And that's my solution for everything is I'm just going to buy technology. I don't need consulting firms. I'm just going to do it myself. But what I'm seeing is that companies of all sizes, but especially mid-market and enterprise, the amount of change that they need to go through in the next three years to make sure that they're not the next blockbuster going bankrupt, that they really are evolving with the times, there's too much emotion, there's too much change management. It's too easy to point to somebody and make them the ones that failed. And so I see this resurgence of needing consulting firms to come in and do the change management and to hold people's hand. And to kind of de-risk it to say, Hey, I'm looking at your competitor and they're doing X, Y, and Z. I've got this higher up view and guiding people around. So, I see this need for change management and transformation to help companies get there faster in the next three to five years that I never like as a software person, we didn't want to have professional services. We didn't see the value in it. And now I'm like, wow. We are underestimating the amount of change management and the human element to change management and the amount of - we often don't, we're not utilizing our best assets. Like if you want change, who are your leaders that are best at facilitating change management? I've seen companies that have invested so much into AI, but over half the organization doesn't understand the value. So what they've really failed at is not the investment in AI talent. They failed in their communication strategy. So like, I really see this opportunity for transformation and change management in a way that I think is critical and is going to define the winners from the not winners. And I'm excited because a lot of that comes down to understanding how to unlock everybody's potential. It comes down to aligning everybody towards a common goal. And it comes down to, finding a new way to lead people through this where we're all aligned to the benefits of it versus the fear of failure, that fear of what happens if we get it wrong, that fear of perfectionism, not working out that fear, that I need to control everything so I can guarantee that this transformation is going to be successful. Like it's messy, but I feel like, there's something really exciting and powerful there that really keeps drawing me into it. And so, we've been talking a lot to partners and how can we partner technology with professional services to help get that adoption so that everybody can benefit from it as quickly as possible.

Mark Cleveland (1:06:47)
Humans are delightfully messy. And so are the organizations that we're a part of. And it's wonderful to have people like you thinking through the opportunities, thinking through the best pattern matching, the best ways to approach innovation and building companies around it for scale. It's such a pleasure to have you on the podcast today, Caitlin. I'm honored and let's do this again.

Caitlin MacGregor (1:07:10)
Thank you so much. This was great.