Dru Armstrong, CEO of Affinipay’s Path to Success

Speaker A: Welcome to Shesess Unplugged, the podcast where we dive deep into the world of female leadership in the private equity SaaS industry. I'm your host, Christine Maslin and I'm on a mission to spotlight the incredible female CEOs who, uh, are making waves in our industry. Join us, uh, as we embark on a journey to explore the triumphs, challenges and pivotal moments in the careers of 12 extraordinary female leaders. Over the course of 12 episodes, you'll hear firsthand from these trailblazers as they share their insights, experiences and the secrets to their success.

Speaker B: Today we're honoured to be joined by Drew Armstrong, um, CEO of Affinipe. Drew has an incredible career story, transitioning from law to private equity and then into leadership roles across SaaS and FinTech. Under her leadership, AFINOPE has achieved remarkable growth, including the acquisition of my case and expanding into accounting. Her strategic vision and commitment to innovation have firmly positioned her, uh, as a pioneer in the fintech space, adding to her very long list of accolades. Drew was recently recognised by American Banker as one of the 2024 Most Influential Women in FinTech, an honour that highlights her positive impact on the industry as a thought leader and CEO. Today we'll delve into her career journey, leadership philosophy and the strategies that have driven transformative growth at Affinipe. We'll also explore her thoughts on diversity, mentorship and the future of fintech. Drew, what a pleasure to have you on. Thank you so much.

Speaker C: Hi, thanks Christine. I'm happy to be here.

Speaker B: So can you kick us off by sharing your journey to becoming the CEO of Affinipe? What were some of the key moments, personally or professionally, that led you here?

Speaker C: Yeah, I mean, how far back do we want to go? You know, I grew up in Los Angeles. I was the daughter of an attorney and I got to watch my dad be a world class attorney and really struggle with the business side of running a medium sized practice, a small practice, a solo practice. And so I went off to college and graduate school thinking I was going to be a federal prosecutor or a litigator like my father. And I got to law school and I realized that that wasn't what I wanted to do. And I realized really quickly. I still finished law school, but I also added my mba and I worked for the Boston Consulting Group and realized that this was where I was meant to be and that I was really passionate about solving business problems. And I got exposed to a lot of different kinds of businesses. I worked with private equity clients and ultimately moved over and got to work on A mid market fund and work on both the deal side and then with the portfolio company CEOs. I loved the partnership and the pace and the ability to kind of impact the trajectory of a business with that kind of focus and partnership. I did a startup with friends in San Francisco. I think it's a badge of honor in tech if you've done a failed startup and then ultimately got recruited back to be the CEO of a company called Grace Hill. We were the pioneers of online training for the property management business, which doesn't sound very sexy, but in fact it's uh, a people intensive business. And I got to experience being a CEO at a young age and working really closely with my mentor who was the chairman of the board. He took a chance on me to promote me to CEO and I really got to transform that business in partnership with the team there and with our clients and with two different amazing private equity funds, the Riverside company and then Stone Point capital. We took we3x the business, we did acquisitions, we did organic product launches, and we really transformed it from a single product company into a platform with multiple products and a much bigger value prop and market opportunity. And so I learned a lot and really developed a passion for getting to be CEO, getting to build teams, set strategic vision and drive value for our customers and then ultimately for our shareholders. So that was my first baby CEO job, as I like to call it. And then when I got the call from Amy Porter and our investors TA about the uh, affinity pay CEO opportunity, I saw the opportunity to take the amazing business that Amy had built over 15 years, which had really pioneered verticalized payments for the legal industry and then the accounting industry and ask the question, what else can we do right and have the right partners in TA and our board, get to build an amazing world class team and really set a much bigger strategy and vision for the, for the business that we've been executing on. And so it's been fun to go from being a verticalized payments company that was world class to a world class software and um, embedded payments and fintech company. And so I've been at Infinite Pay for three and a half years. We just brought in a new investor and we've been building the business which takes more time than you would think it takes. But it's been an amazing journey. I think when you have that magic combination of great company customers that love your product, really engaged happy employees and um, then great backers, it's a winning combination.

Speaker B: Thank you for sharing, Drew. I mean, you're clearly very passionate, uh, about Telling the story, and it's a great story. And congratulations on the investment last year.

Speaker C: Thank you. It's a weird market right now, I think. I've been CEO for nine years of private equity backed companies. Longer than that if you count being CEO of a startup. And I've taken companies through three different transactions successfully. And I think the market that we're in today is still very weird and uncertain. So we felt incredibly privileged to be able to go through a successful sale process and bring on Gen Star and have Jenn Star and TA as our investors.

Speaker B: Yeah. And what great investors they both are as well. Yeah. Uh, and I agree the market's been quite strange for the last few years. So you definitely did well to secure that investment last year. And I think that's, obviously that is because of the value that you've driven during the, you know, during your tenure as the CEO at Finnipe. And you know, just listening to your career journey and story almost seems like everything that you did was like the perfect combination of experience to set you up to take on this role and then, you know, the kind of legal background combined with the SAS experience and now FinTech. So, yeah, great to listen to that. Thank you.

Speaker C: Yeah. And I, I guess I would say I think sometimes being a, uh, young CEO, you feel a little bit like you're on a hero's journey where you kind of leave the safety of big corporate gigs or private equity gigs. And you know, uh, there's a really good Harvard Business Review article about how to become a CEO young in your career. And usually it's you take on a mess, you take a step back. You know, there's like different attributes and it rarely is on the surface sexy and exciting and you know, they usually don't give you that necessarily like the coolest, easiest jobs first. So it's funny in retrospect, it kind of all adds up, but there were definitely many years where I was like, what am I doing? I'm living in Greenville, South Carolina. I have two really young kids under five, and I'm working in an industry that I didn't know anything about, um, on products I didn't really know. And so you just have to kind of have faith that if you feel like you're, you know, building cool things, solving important problems and working with the right people, that it will ultimately pay off. But it certainly wasn't a sure thing for many years, I'd say.

Speaker B: Yeah, and that's great insight as well. You know, stick with it. Even if when it feels like it's not necessarily going where you want it to go. Right. And you're, you're proof that it, you know, that it works out in the end. So we've already talked about this a little bit. You transitioned from law to private equity and then into leadership roles in SAS and in FinTech. What inspired these transitions and how have these diverse experiences shaped your career?

Speaker C: Yeah, I mean, I think it's really important to know what your strengths are. I think when you start out in school and early in your career, being good at a lot of things is what gets rewarded. Right. In American high school, it's, you've got to be an athlete, you've got to be, you know, I was a debater, I was a class leader. Uh, you had to be good at all the subjects. And I think the contrast between that and a successful career is continued narrowing focus on what you're actually exceptional at. Right. And where you can add the most value. And I think people should take advantage of the early times in their career and their schooling to start to hone their own self understanding. Right. Which is, hey, I'm in this environment, culturally, does it align with me? Does the work excite me? You know, is this a team I can learn from? And do other people seem happy while I may not be happy? And so I had spent many years thinking that I really knew I wanted to be a lawyer. I did work in undergrad, I was paralegal for the district attorney's office. I was a trial assistant for a mob defense attorney in Brooklyn. And I thought I really knew. And then I went to law school. And within a quarter I realized this is not, and it's a very academic law school. So it's not every law school isn't the same, but University of Chicago is incredibly academic. And I just felt like a total fish out of water. And so that kind of set me on the path of, well, if I don't love this, then what do I love? And I did two different summer internships and I still didn't get any closer to feeling like this is the work that I'm meant to be doing. This is where I'm going to be happy. Because I do think happiness contributes to our ability to be really successful. And then I went to private equity. I did Boston Consulting Group. I loved it until I didn't. Everyone says you're like two hard cases away from moving on. And I loved the intellectual work. I loved setting strategy, using data and insights to make hard, strategic business decisions. But I didn't love the client management side as Much. It just wasn't as exciting. I could see that became more and more the job. And then I went to private equity and there were things I loved about it. Culturally. The fund that I joined was not a fit for me. And one thing that I like to encourage people to do is to say, you know, we don't live in the Mad Men era anymore. There's a lot of different cultures out there. One thing that you're told when you become CEO is it takes seven years to change culture if you're the CEO. So if you join a business and you say, gosh, this just really doesn't fit me, I don't feel included, I don't feel like my voice is heard, I don't feel appreciated. You know, it's not to say you should quit when it's hard, but if it really isn't a fit, I think trusting your gut and knowing that it's time to move on. So I loved the work, but I didn't love the culture and couldn't see myself there in the long term. And so that kind of kept narrowing me back to. I loved working with the CEOs of portfolio companies. I love setting strategy in business. It took me becoming a CEO to realize how much I love to build teams, which I think is really the primary job of a, uh, CEO. That's what I spend a lot of my time doing. It's the hardest part, it's the most rewarding part. And so that kind of pushed me into the operator side of the world. Right. Actually being in the business, being accountable, making decisions, building teams. And so it definitely was, you know, not a straight path. And I think people shouldn't be afraid to make changes. You know, I was more senior in consulting and I took a step back in private equity. It's really hard to change. I took a step back when I went into an operating role and then got promoted really quickly to CEO. So I think it's a lot of chutes and ladders in terms of where uh, you ultimately end up and a lot of trusting your gut and your own self awareness around where you're going to be most successful.

Speaker B: Yeah, really, really interesting. Thank you for sharing and you know, really great advice for our members and listeners. You know, know your strengths and narrow, uh, your focus. Uh, you know, the stories that you've told around like joining companies and realizing or you know, studying and realizing, this isn't for me, I'm not enjoying it. It's quite a bold, brave decision to, to say I'm not going to do this anymore because this isn't for me. And not everybody does that. You know, they. They don't. Lots of people end up staying in careers that, uh, they don't enjoy. So I think bold move, which obviously paid off really well for you. And I think great advice for anybody listening around. Do what you do, what you enjoy. Be happy is so important. You know, I couldn't agree more. Thank you.

Speaker C: Yeah. And I wouldn't say, I mean, look, there have been times where, you know, the job is hard, it's not all fun. It's still a job, and you have to persist. And so it's certainly not a message of just kind of like sometimes, like, I've done a lot of executive hiring, and you look at resumes and people have been like the. The butterflies where they aren't in a job even two years. Every job is a year, year and a half. And so you do want to have longevity and you want to kind of. It's hard to build businesses quickly. I think that's sometimes the dance that we do as CEOs with investors, as. As the markets got better and better, the whole period shortened. And so part of the challenge is creating exceptional amounts of value in very short periods of time, when actually building value and, um, with companies and customers takes time. And so figuring out how to accelerate that value creation. So I certainly wouldn't say, like, don't, you know, stick with it when times are rough. But that's after you validated that this is where you feel like you should be and you've made a commitment and you feel like it's workable. So, you know, on one hand, I, uh. It's like the cheesy saying, but no one to hold them and no one to fold them. And that's actually where I think mentorship comes in, is usually mentors can give you a pretty unemotional perspective, and if they know you really well, you know, I've had mentors say, I know this. You know, you're kind of tired. You don't necessarily want to be living in Greenville. You don't, you know, you don't see the end of the road, but you need to stick through this because you committed to this chapter and see it all the way through, and then know that on the other side of that will be more opportunity versus sometimes they'll say, you know, you're right. Like, this doesn't sound like a tenable situation. Let's find. Let. Let me help you find something else.

Speaker B: Yeah, no, good. Yeah, good advice again. And I completely Agree. You know, and it's just knowing and, um, um, being able to be honest with yourself around. Is this really not for me, or am I just having a hard time right now and do I just need to spend a bit more time, you know, do I like the sector? Do I like the people? And it just comes back down to, you know, what. What you've been saying about is the culture, right? Are the people right for you? And I think if that's not right, then it's going to be very, very difficult to get anything else done. And you'll know that pretty early on. And I suppose, you know, our, uh, members and our listeners, as they're more experienced people, get to know themselves, and when they're at an interview, they realize, you know what, this person's perfectly nice, but I'm probably not going to click with them. They're not going to be my type of person to kind of be on mission with. So, yeah, good advice. What challenges did you face as you rose through the leadership ranks, and how did you overcome them?

Speaker C: Yeah, it's a good question. You know, I think that sometimes the challenges that we face at the time are only evident to us in retrospect. Right. I think that there's a certain amount of risk taking that has been involved in my career and sometimes a certain amount of, like, optimism and even naivete in terms of what I was taking on, especially relative to my level of experience. And so, you know, I think there, it's been really important for me to make sure that I had some level of being set up for success as I took those risks. But obviously, you know, I became CEO at a very young age. I had actually never worked in a company before. Right. I was Chief Product Officer for less than six months, and then I got promoted to CEO. I'd only worked in consulting and investing prior to that. So that was a challenge, right? Figuring out how to run a company, never having worked in one, you know, and it's funny, I had a mentor say to me, drew, anytime you sit in the CEO seat, it's new and hard, even if you rise up the ranks. So it's hard for everyone. Just know that. And he had ascended to C after being COO and many leadership roles prior to being CEO. So he's like, just trust me that sitting in the seat is hard no matter where you're entering from above, sideways, below. So I think that was really challenging. You know, I've definitely faced kind of discrimination and sexual harassment earlier on in my career, and that was part of My kind of recognition that it wasn't a good culture fit for me. And I think, you know, I think as a. From a pragmatic perspective, my goal was to kind of minimize and move. Move on from that as quickly as possible. And I appreciate the fact that culturally, we're far less tolerant of that than we were 15 years ago. Right. I think a lot of what my generation, the generation before us, faced, hopefully, is just not tolerated anymore. So definitely overcame that. I think as you go further on in your career, though, the overt discrimination can sometimes become subtext. Right. And so you sometimes ask yourself, you know, would they ask a man this question? Would they challenge a man? Would they extend him the trust? You know, am I getting treated like the seasoned CEO with the track record that I have that. That, you know, am I getting treated the same way that a man would get treated? But personally, I've found that, you know, obviously it's okay to ask those questions and talk to your girlfriends about it and talk to your mentors and your support system, you know, but usually I just kind of persisted and answered the questions and picked the priorities that I thought were important for the company. And the more that I stayed focus on. Focused on the fundamentals of what it meant to be a good CEO, the better, you know, it went. Right. And the CEO has a pretty hard job, but a pretty straightforward job. And so, you know, I'd say I've probably seen it all, from business challenges to challenges, being a young woman and having to overcome that. Though I do like to say I think one of my superpowers is being underestimated. And so sometimes we gotta take those challenges and turn them around. And, you know, we've made big strategic moves that others didn't think we could do or didn't see coming. And so, you know, I've always kind of had that mindset of being able to kind of overcome and exceed expectations, and then also who you partner with and who supports you really matters. I'm very blessed that most of my mentors and sponsors in my career have been amazing men. Right. And a lot of my board members who took chances on me and promoted me to CEO or, you know, gave me the infinite opportunity. There's just been a lot of great people, and it was not on gender lines. Right. And so I think it's about aligning yourself with people who really focus on performance and focus on investing in you as a person. And that's how you can kind of sidestep some of the other more treacherous parts of trying to Rise to the ranks. Especially as someone who is, you know, not the typical picture of a CEO.

Speaker B: Yeah, agree. Couldn't agree more. What values and um, principles guide your decision making process?

Speaker C: Oh, huh. That's a good question. I mean, it's probably boring to say integrity. Right. I think the thing that originally made me want to be CEO and it came out of working at BCG was just, you know, wanting to be the person in the seat who got to make decisions that were right for the customers and right for the team and really wanting to the best of my ability, you know, do that. And so I think it's important that. And we, we just wrapped our company kickoff yesterday and we talked about, and we have a great board member and he says that happy customers plus engaged employees equals success. Right. And so I think if you kind of put those two things, your customers and your team at the top, then it will be a winning formula. Right. And so I think that's been a big part of it. I also really trust my gut and my intuition and I'm not someone who needs never ending amounts of information to make decisions. And you know, it doesn't mean I always get it right, but I get it right a lot of the time. And um, I think experience feeds that intuition, but also, you know, what feels exciting and what feels like it's going to be rewarding. And so some of my decisions at the time seemed kind of nonsensical in terms of, you know, left San Francisco to go run, you know, 15 million ARR training business in the property management space and move to the South. Right. Well before everyone else was doing it. But I was an opportunity to work with my mentor and a private equity fund and sit on an exec team and it just seemed really exciting. And I, you know, turned down a job at Google where I probably would have made a lot more money to go do that because it seemed fun and exciting and impactful and it's felt like an adventure. And we were ready to buy a house and we couldn't afford that in San Francisco. So sometimes it doesn't have to be perfect on paper and you don't have to have a spreadsheet of criteria to make some of those decisions. And so I've always had a little bit of a penchant, uh, for risk taking and following, you know, what felt to me like it was gonna be exciting even if other people didn't think it seemed very exciting at the time.

Speaker B: Yeah, I know. Trust in your gut. Yeah, that's a good one. And another brave decision. You know, you get a job offer from Google and then there's this kind of 15 million ARR. Business m. Most people like okay, you know. But no, you obviously knew that that was the right, the right move for you and was proven. Right. Great.

Speaker C: Yeah. And I knew I wanted to be a CEO and it's kind of being core to who you are. Like I'd much rather have the opportunity to run a company and build products and serve an end market and even if it's you know, not at Google, like to me that was really exciting and felt like a uh, calling to me. And so I was willing to take the leap, you know, of faith thinking that that could lead to me being able to fulfill my dreams. And it happened much faster than I expected. So sometimes those risk really pay off in ways that you don't necessarily expect.

Speaker B: Yeah, no, it's a good story. And I think that those risks don't always pay off for people. Right. And that's where trusting your gut comes in as well. And then being willing to fail at something which also helps to shape your experience as a leader along the way. How would you describe your leadership style and how has it evolved over the years?

Speaker C: Yeah, I used to think that the hard uh, stuff was the hard stuff. So m, the math, the analytics, the intellectually solving the business question, the setting, the strategy. I think a lot about there's kind of three core jobs that a CEO has to do. One is set vision and strategy and your corporate priorities. Right. It's kind of the what we're going to do. And then two is build the team, build a world class team to execute on it. And three is make sure it builds immense value. Right. For employees, shareholders, customers. And when I started my career I was very focused on 1 and 3. The longer I go in my career I really think number two is what drives one and three. And so it's sometimes probably annoying to my investors that when we talk about results and if we're not getting the results that we want to see, I uh, talk about the team and what we need in the team. And you know, the reality is the bigger the company gets, the less you as CEO actually do. There's kind of nothing that I can say we're going to go do this and I could do it alone. Right. It really takes a village. We're, we're over 600 employees today. We're relatively big software fintech company. And so that's where my leadership style has evolved from being. You know, I hate to say it cause it's embarrassing now. Like the smartest one in the. That was like, you know, for many years I'd been an analyst longer than I had been a CEO. And a lot of that has shifted towards the magic that happens when you build the right team with diverse perspectives and depth of experience. And frankly, a team that complements, you know, my strengths and fills in my weaknesses. Right. I think that's another thing that's kind of unique to being CEO is that a lot of who I look to hire are people that are experienced in ways that I'm not, functionally masters of things that I'm not, and frankly just have mindsets very different to my own. I'm big picture, go fast, high impact, kind of typical CEO. I look for people who are good at process and good at asking 5 million questions that I used to think were annoying and would slow me down. Now they I'm like, oh, you're asking all the questions so we don't jump off a cliff, you know, without a parachute. So a lot of it is about that team and the team dynamic. And I really believe that high performing teams, it's based on people who like each other, who trust each other, who want to be together. And that kind of carries you through the good and the bad. Right. And so I don't, I'm not interested in spending all my time at work with a team that doesn't get along, that's contentious, that isn't really operating and functional.

Speaker B: Yeah. Very, very good. Very honest and humble answer. Thank you. Diversity and inclusion are obviously critical topics today in leadership. What specific steps have you taken to build an inclusive and diverse culture at Infinipe?

Speaker C: It's such a loaded topic right now because I, you know, I guess going way of the dodo bird. No, I'm kidding. I mean, I'm a diverse leader. Right. Just from a gender perspective and you could also say from an age perspective. And so it's, I think it's innately my culture. And I think where De and I fails is where it doesn't serve the purpose of the performance of the company. Right. And I think that's where sometimes it can go too far from our perspective. You know, you have to kind of look at from like a funnel all the way through, from a talent funnel all the way into your team. So from a recruiting perspective, every role that we hire for, we aim to have diversity in our pipeline. And if you have diversity in your pipeline, then you have a shot at having diversity in who you hire. Right. And you have to ultimately hire the Best candidate, regardless of demographics. And that's what we've done. But we do really focus on making sure that the candidates that we're considering are diverse and that we have a range, because otherwise you have zero chance of hiring, you know, diverse employees. So I think that's one piece. Number two is we work really hard to culturally reward diverse perspectives. And I don't mean that synonymous with demographics. I mean it, uh, in terms of different mindsets. We use personality testing. We use TILT360, which I learned when I joined the company. And it's kind of a really simple version of disc that buckets people into four categories. We do not use it to determine who we hire. We like to know it going in, but we use it to find ways to better communicate with each other. And so part of my self awareness that, you know, I'm an impact type, which is big picture, go fast. And my cfo, who's, you know, the one of the people I work most closely with, he's the exact opposite to me. He's a clarity. And he's. That means he likes to always be clear. He asks a million questions. And so we're kind of the gas and the brakes, right? And if you're able to go into a meeting and as someone who used, uh, to get really annoyed and almost offended when people ask me a million questions. Cause I was like, they're slowing my roll. This is a great idea you're holding me back from. Let's just go do it, right? And then you begin to appreciate, oh, he's a clarity. He's going to ask me the 5 million questions. My COO is a structure. He loves process. He's going to be like, but how do we do it? And then my GC is a connect, and she's always like, but who's gonna do it? Is the team gonna like to do it? Can that team do it? So, you know, we spend a lot of time and we do it. Every single person at the company does it. It's a big part of how we talk to each other, hear each other's ideas. We look at, you know, we used to have pretty much all clarities and some structures and no impact in connectors. So we kind of look at that and use it as a way to help us communicate with each other. And then I think the third part about this is really the culture, right? This is the foundation of the company. And so we do a lot to celebrate and reward the culture, which is really the behaviors that you want to see. And we do that. And it's something that I would say we get immensely positive feedback from candidates, and both candidates we hire and candidates we don't. In terms of being able to get a very clear sense of the culture. Even when they're interviewing that oftentimes I'll. I'll interview execs and they're like, I talked to you and it was great. But then it just got better and better the more I talk to your team, which I don't know if I should be offended by, but it's this idea that, like, underpinning this is like these core values that we all share that we all celebrate. And so that's kind of the commonality and then finding ways to really be inclusive of a lot of different voices and perspectives. And look, no company gets it perfect. Every company has things that they're working on. I think the companies that have been loudest about how important De and I is, Apple started their program in the 80s. You know, Costco started their program, I think, almost 20 years ago. So this is a journey, right? It's kind of like culture. You don't wake up one day have a one year initiative on culture, and then you're done. This is like a constant commitment to how you operate, how you build teams, your core ethos of how you operate. And I think for us, because we had a female founder and we now have a female CEO and we've got over 40% of our team is female. And, you know, we just feel like it's part of what makes us tick. And frankly, it reflects our industry. So over half of law grads today are women. And so I do think it helps when you're kind of able to hold a mirror up to your clients and they see themselves. And so, you know, I think there's a lot of opportunity for companies to do it in different ways, but ultimately in ways that make people feel appreciated and like they can stay and grow their careers. And it's a strategic advantage if you can get the best talent.

Speaker B: Yeah, thanks, Drew. Yeah, it sounds like you've built an incredible team with great awareness and great culture. Congratulations on being named one of the 2024 most influential women in fintech by American. What does that mean to you and how does it reflect your work at Affinipe?

Speaker C: Well, it's funny, until I came to Affinope, I'd never been at a payments company. I had never thought about fintech. I came out of the SaaS, the vertical SaaS world, and a lot of the vertical SaaS world or the product mindset is it's super powerful if you can identify really important problems that your clients have that you can then uniquely solve using technology, right? And I think that's a lot of what software does, right? And I think that's the magic of software. And what has been really exciting and energizing for me that I realized kind of very early on in partnership, we've got an amazing team that knows payments incredibly well. Christian, our CFO will tell you he started when payments was knuckle busters and he's like, thank goodness it became technology as it evolved. And our investors, you know, a lot of them have massive pattern recognition and payments in fintech. And early on what got me excited was the conversation that was like, this is another way, an um, another way to use technology to solve core problems. And a lot of what you're trying to figure out when you're building products and software companies is like, what problems are worth solving? Like, you know, what are people willing to pay for that? They're that important. And what we've seen is like, what's more important than the financial wellness of a firm? You know, if you look at that firm, so much of what lawyers and accountants struggle with is not the client work, but how to grow their business, how to have their business thrive, how to make money while they're able to then focus on their clients. And so what was really exciting to me was the idea that because of our payments DNA, we really understood the power, power of moving money. Right. Payments is kind of the OG Fintech product where it said, um, lawyers were tired of chasing invoices, they have massive write off challenges. You know, there's massive leakage in their firms because they're, you know, not able to get paid quickly and effectively. And digital payments help solve that. And, and we said, look, we know how to handle risk, we know how to handle underwriting. Like we understand these kind of core components and what it means to then bring them to the surface with digital workflows. And we said, well, what are the other financial needs of the firms and where are they not being addressed by more traditional financial institutions? And if we own the workflows, how do we embed them? And so what's been really fun for me is with the team being on this journey to identify lawyers have a really hard time getting loans and access to capital. They need, you know, merchant cash advances like any other business to help make payroll or fund filing fees. They've even a hard time getting a corporate card like a, uh, traditional credit card. For their business and so much of it they have to do personally and it may not be enough. Right. Like they don't have a single pane of glass on their financials. So of course it's hard for them to understand how their practice is doing. And this is where I think, you know, software and embedded finance can really fundamentally transform a practice and transform their business and we can do it so that they can focus on their clients. So it's for me, I never set out to do fintech. I didn't come from the traditional payments or banking world. But I'm really passionate about product and solving our clients problems and solving ones that really move the needle for them. And I think Fintech is proving to be a pretty powerful tool to do that. And I'm very fortunate that I joined a company that has so much deep expertise because a lot of people want to do fintech but they don't want to do the financial services part. And yet that's what's required. So it's been an amazing journey, an amazing learning experience and I'd say you should expect to see the rate of innovation from us in that area going faster and faster because we're now have already launched two products and we've got more coming and you just get better and better at it as you figure out the market and how to do it.

Speaker B: Sounds exciting and thank, yeah, your passion certainly shines through and congrats again on uh, the award. So let's talk about value creation. We touched on this a little bit at the beginning. During your time at Grace Hill, the company experienced transformative growth and was acquired by Aurora Capital Partners. Could you walk us through that journey and your role in making it a success?

Speaker C: Yeah. So we did two, I did two chapters as CEO. So the first one was around building a market leading position for the original business which was online training and property management's a really interesting business because in essence it's a staffing company to manage multi million dollar assets for local national global asset managers and real estate owners. Right. And and yet oftentimes you're recruiting straight out of the mall. Right. Like so Abercrombie and Fitch and J. Crew and you're hiring your kind of frontline employees who are the face of your brand and uh, man and are all the risk in your business to manage a multimillion dollar asset. Right. And so we were created originally by the founders to solve that need to train them both on their skills and on the compl risk and then the next chapter with Stone Point Capital was around, well, if we can solve training, what else can we solve? To really bring together all the people challenges and solve it in one place. And so that was transformational in the sense that we introduced this idea of being a people performance platform. And we said, look, you can bring the policies together and that's what you want them to do. The training, it's how you want them to do it. And then all the people assessment piece and it really brought together all these different point solutions that property managers were having to use to manage their team. And we created a single platform experience and really unified them, using data to help them drive improved performance. And I think one thing that was fun for me was like, you see that the on site turnover is 50% for the residents and that directly correlated with the staff turnover. And so companies that were investing in the operations and the training and getting their team set up for success had lower both employee turnover and resident turnover. And so it was really exciting. And the cool thing about these great companies is we sold and I was ready to start my new chapter. And I had this amazing woman, Kendall Pretzer. We had bought her company, she had built the, you know, leading policy management software and then she became CEO. So now I'm an investor and supporter of hers and she's one of my closest friends. And so it was a really amazing journey to kind of go from this single product company to a multi product company, to a platform and to also. I learned so much from her on how to build a team. And so I learned a lot in that experience. I also got to learn what it felt like to work with a world class investment fund. Stone Point Capital was just amazing partners. They took a big bet on me and they were the ones who were like, we don't have operating partners. You get to go figure out your value creation plan and we back your strategy, which felt very different. And so it was an amazing experience. It was hard. It was really, really hard. But I was really proud of the work that we did there. And sometimes we get so caught up on the size and scale of businesses that we want to kind of jump forward. But I think sometimes the, the harder companies, the companies that are serving more vended markets, it really teaches you, you know, kind of what the levers are to pull because you're so focused on it. And then when you go to other markets and bigger companies, you're like, oh, this is a little bit easier, there's more tailwinds, there's more greenfield. But all that kind of DNA about being willing to do the hard work, the unsexy work does pay off and translate into, you know, the next opportunity.

Speaker B: Yeah, wonderful to listen to. That's a great story and I could probably ask you lots more questions and we could talk about it for much longer but we have limited time on this podcast unfortunately. But yeah, thank you for sharing that. And uh, moving on to current day Finnipe and we've again talked a little bit about this already but the company's grown significantly under your leadership including the acquisition of MyCase and the expansion into accounting and the recent transaction or investment from genstar. What have been some of the more impactful strategies for driving value and growth at finnepe?

Speaker C: Yeah, I mean a year into joining we made what was a massive strategic pivot which is to go from being kind of a Switzerland vertical payments company into being a software plus embedded payments and fintech company and anyone who knows payments. That's about as big a strategic shift as you can make. And obviously we were able to buy one of the market leading legal practice management platforms. And so one thing we talk a lot about is that was only two and a half years ago. And the amazing thing about building a market leading company in large end markets with a lot of greenfield. So you know 65 plus percent of lawyers and accountants have yet to adopt cloud based practice management in the solo small and medium segments. So there is a lot more tech that these firms are going to be adopting and the strategic imperative around adopting it is only increasing. Between the COVID pushing everything remote and hybrid and then obviously now gen AI. Each of the verticals have different reasons for needing gen AI accounting. It's people don't want to be accountants so they need to automate and uh, the demand for their work is only continuing to increase with law firms it's around efficiency and ability to kind of, you know, better align supply and demand of legal work and probably pricing around that. So that's all to come. But I think what's exciting for us is you know, we've been really investing in our foundation. We're 3x bigger than we were. We are a rule of 65 company, top and bottom line growth and yet we still feel like we're just getting started, right? And we just recruited in new go to market leadership, a new chief revenue officer, a new cmo and when you guys say, you know, we've got hundreds of thousands of firms we're going to target and we're going to build great products and we're going to partner for great products especially on fintech and Then we're going to go buy more world class platforms and products. You know, the future feels very bright. If anything, our biggest challenge is what to focus on because there is so much opportunity. And so every year you just have that list and that ambitious growth goal and profitable growth goal and you just execute on it with the team. And so when I joined I was like, this could be, I could be at this company for a decade plus because there's so much potential. And what got me really excited was just seeing what Amy had built and they were 100 million of revenue, really doing one thing for one end market with massive customer love and super engaged employees. And I was like, what a great foundation to start from. And so we've been on this transformational journey and I think it's really fun, right? It's really, really fun. It's really hard. And you need a lot of things to go right. You need the right investors and you need the right team M even more than the investors and you need the right strategy. But we feel really good about it and I think we took a big risk that a lot of companies wouldn't necessarily have. I think there definitely was an off ramp and I give a lot of credit to Ta and Roy and Clara, investors who supported us in wanting to really open up the strategic aperture and be able to build this really amazing world class software company and go on that journey with us. So it's been fun. It's been hard, you know, but it's a pretty amazing thing to get to do.

Speaker B: Yeah, it sounds really exciting. It does sound like a lot of fun. And I shall certainly be keeping an eye out for the explosive growth, continued explosive growth, you know, that's yet to come. Is there any advice that you would give to other female leaders or other leaders navigating high stakes transactions or leading companies through periods of change?

Speaker C: Yeah, I think people really, you know, people want to kind of trust their leaders. Right. And I think you build trust through transparency and honesty and vulnerability. And I think the generations coming up really appreciate when people are authentic. And I think sometimes that term has gotten overused. Right. Every brand's authentic. Like we went through that. Everything looked like it was from the farm or something. But I think in leadership, you know, we're craving a different conversation, a more human conversation. And I think when you give people reasons to trust you and believe you and, and then you kind of do what you say you're going to do, you know, that will, that will help attract and retain a team that wants to go on that Hard journey with you, right? If you say, look, here's how we're going to go build a business. Here's why we think this is going to be transformational for our clients, here's why we think it's transformational for you. I don't have everything figured out, but here's like world class people that we've hired that fit our culture who've been on this journey before. Like, trust us, we're going to go figure this out together. And I think we're in this really big time of switching from command and control, top down leadership, which worked in a much more static environment where change didn't happen constantly. We need folks at all levels of a, uh, high performance company to be generating ideas, to be on the front lines, to be thinking about ways to serve our customers better, to think about new product ideas, about ways to build software better, all these things. Command and control does not work anymore. It has to be a learning mindset. It has to be people willing to be agile, adopt new technology, try new things. Like the rate of change is just too great. There's no world where, you know, I've got an eight person exec team, like we can go be like a cabal and come up with all the great ideas and just push them down. And so I think that just sets up a very different type of leadership model and culture model. Right. I mean it's why we believe in a hybrid work workforce. I loved that Spotify did the billboard saying we treat our employees like professionals, not children. Right. It doesn't mean we don't have expectations about being in the office and showing up to the kickoff and being professional. And you know, we're in the office three days a week, but we also are like you are professionals. Right. And so when you're not in the office because you're doing 10 demos today for customers, like I'm going to manage you on your outputs unless you give me a reason to manage you on your inputs. And so, you know, we've really embraced kind of the new model of leadership and I think it's allowed us to attract great talent and keep great talent. So I think it's an exciting time for leaders that are willing to kind of look in the mirror and embrace the new.

Speaker B: Great. Yeah, agree. Thank you, Drew. Moving on to a question that uh, I, uh, love to ask all the successful high profile women that I interview and it's about balance. How do you manage a demanding career, family life, in your case, I think two young boys and your personal well being and what strategies have worked best for you?

Speaker C: So number one, and it was interesting, I had a female employee, employee who just had her first baby, asked me the same question yesterday at kickoff. And number one is it takes a village. And sometimes you have to pay the village. So if you need help, get the help you need. And I will tell you, you know, when my kids were really little, there were years of feeling like a lot of my paycheck went to paying, um, nannies and babysitters and support. My husband also works. And so I just wouldn't be ashamed of that. And I think that can even cover sometimes we get a babysitter on Saturday morning. So I can go to a soul cycle and my husband can go for a long ride. He loves to ride bikes. I don't know why, but he does. And you know, it's like, that's not selfish. That's part of what gives us balance and energizes me. And then I come home and I see my kids all afternoon, all evening, and it doesn't take away from them. If anything, I think the happier we are, the more our kids flourish and the more that we know ourselves and invest in things that make us happy and they see that it gives them space to do the same. And then second is, I'm very blessed. I have an amazing partner. My husband is a wonderful father. And we really are 50, 50 split on, you know, being parents. And if I have a late night working like I did last night. Cause we had our company kickoff and a party, like he covers the kids. And so, you know, it was interesting. The gal I was talking to, she said, you know, cause I'm here this week. He got up and was like, it's so great. I get to bottle feed the baby in the morning. And it's such a special time. And she was like, oh, I didn't even think that you would want to do that. Right. And so I think creating space for other people, if you. If they're available to you, some people are recognized, that's not an option. But if you have. My experience was like, my husband wanted to help take care of the kids. The grandparents wanted to help take care of the kids. So back to the it takes a village and that, you know, it doesn't take away from us as moms if we do that. In my opinion, and I would la. The last comment is, I think as a culture, I hate to say it, but that Barbie monologue, like people love to judge and everyone loves to judge.

Speaker B: Judged. If you do judged. If you don't Right.

Speaker C: Yeah, like work, but don't work too hard. You know, be successful, but not too successful. Travel for work, but not so much that, like. But what about. What about your kids? You know, it's like, good Lord, there's no winning. So just have your. Have your, you know, your safe circle that loves you and supports you and doesn't judge you because you don't need any help getting judged. The world will do that. And just know yourself, right? And go back to the. You're doing what works for you and your family. When you come home at night, no one else gets to judge how that runs, how that operates. And just tune it out and find people that align with how you're thinking about building your life and your career and creating that balance. You know, tune out all the haters. Haters are going to hate.

Speaker B: Yeah. Yeah, I like it. Uh, thank you. Drew, reflecting on your career, is there anything you wish you'd known earlier that you think might benefit our listeners?

Speaker C: I think I was really young and impatient to get where I wanted to go, and I think that was a good thing, and I think it was a bad thing. I think one of the hardest things I did was that first CEO job, the first couple years of being CEO, and if it had taken me five years longer, I think that would have been okay. Right. And so sometimes I think we put a lot of pressure on ourselves to get where we want to go faster. There's an overemphasis on youth and doing things young. And one thing I've learned a lot in my career, I used to think experience didn't matter. It was like a way to not have kind of a growth mindset or change mindset. And I'm like, gosh, experience really teaches you a lot. And wisdom is learning from other people's mistakes. So being willing to, you know, invite in other people's experiences and benefit from them. So if you're not where you want to be today and you're like, why has it taken so long? Just have faith that if you are still very focused on where you want to go and you're putting in the work like, it will happen, it just sometimes doesn't happen as fast. And sometimes that's okay because we get the benefit of learning as we go along. And so maybe when you get there, you'll appreciate it more, you'll be more successful. Careers are built in decades, not in months or even years. And so that's. That's something that I wish I could have told myself younger. Like, don't Worry, don't be so nervous. You will get there. And if you get there really fast, it may actually be more painful. So careful what you wish for, right? So easy to say now.

Speaker B: Well, whatever you did, it stood you in good stead anyway. Is there, is there a motto or mantra or piece of advice that you live by that you'd like to share?

Speaker C: I mean, one of them is like, this too shall pass. So there are times that are really hard and I think that is, that is a big thing that I think about when times get really tough. I. Yesterday I had the opportunity to interview Gabby Thomas, the three time women's sprinting Olympic medalist from the Paris Games.

Speaker B: What a great person to get sko. Yeah.

Speaker C: Oh, my God. Oh, my God. Like, hard to not be a fan girl. She's just unbelievable in the full package. And you know, she talked a lot about, on one hand, success is about consistency and discipline. And that's something we talk a lot about at our company, is like, we get up every day, we work really hard for our customers, and we do it over and over and over. And then that builds towards these winning moments. And she talked about. But when it's race day, she has the confidence that she's put in all the time, all the years. I mean, Olympians are amazing. They finish the Olympics and then like the next week they're back to their two a day training, right? And they do it for four years, not necessarily on the global stage, you know, or the stage that is as, as focused on as the Olympics. And then race day, it's about finding a way to win. And she's like, some of my races are really ugly, but I got it done right. And so I thought those were kind of two great things that you could hold kind of in, in each hand. One is like, just be consistent, just show up, just do the work. Not every day is going to feel awesome. It's okay. Just like the grind, the rising grind. And then the other side is like when it's go time, like being ready to get the deal done, being ready to show up, having done all the preparation, all the work, you know your business, you know your shit, and it's go time, right? And so I think both of those really resonated with me as kind of two ways to think about, you know, achieving.

Speaker B: Lovely. Yeah. Thank you for sharing. So that brings us to the end and I've just got a quick fire round of questions if you're ready for that.

Speaker C: So fun.

Speaker B: Name one habit or ritual that keeps you grounded.

Speaker C: Going to bed Early, Yeah, good one.

Speaker B: I do that too. What's a book, podcast or show that you've enjoyed recently and would recommend?

Speaker C: Oh, my gosh. I just finished Landman and Lioness, and they were both so fun. I read and I watch TV for fun. I'm not a big business improvement person. It's my downtime. It's my happy time.

Speaker B: Uh, I shall look them up. Are they books or.

Speaker C: Oh, God, no. No, no, no. They're Tyler Sheridan, like, popcorn eating tv.

Speaker B: Oh, really? So it's Landman and Lioness. Two separate ones.

Speaker C: I'm gonna look at those. Yes. Yeah, yeah. Both by. So Tyler Sheridan did. What is it called? Yellowstone. You know, the family drama about kind of the big ranch in Wyoming. And then, um, Lionesses, starring Zoe Saldana, and, you know, she's kind of this badass warrior who, you know, takes down the bad guys. And then Landman is about. It's actually set in Texas, and so it's about the oil business and, like, fending off the cartels and John Ham's in it and Billy Bob Thornton, and so it's just. They're both. They're all amazing dramas and very fun to watch.

Speaker B: Oh, great. Well, that's just set my Friday night up um, nicely. I'll just grab some popcorn and.

Speaker C: Exactly. And then Harvard Business Review for good business tips, because they're, like, succinct, to the point, and always very educational.

Speaker B: Okay, good. If you would instantly master a new skill, what would it be?

Speaker C: I would say some people have an innate ability to read people from the jump, and it's something that I've been working on. But my chief people officer, we have an org psychologist we work with, and they just have an innate ability to understand what motivates people, what excites people, what their limitations are. And it's a skill I've been working on for years that I don't know I'll ever fully have, but it would be that great.

Speaker B: What's the best part about being a CEO?

Speaker C: Uh, the team. Working on a world class team that you love going to the office with. And I always say it's. It's not about the team you want to win with. It's the team when you have a losing day, you want to call at the end of the day and you want to have a glass of wine, and you want to laugh about it and pick yourself back up and go after it the next day. So definitely the team, for me, is the best part.

Speaker B: Describe your leadership style in one word.

Speaker C: Collaborative. Really Collaborative. I just think part of what let me be a young CEO is getting to hear the wisdom of others and being able to. I don't. I hate the term disagree and commit. I usually think if, like, the data and the arguments are sound, you're going to agree and commit and move forward. And that's a really powerful place to be in.

Speaker B: Well, look, thank you so much for coming on. It's been a really, really exciting story to listen to and I've personally taken away, you know, some key tips and advice that I think will help me on my journey. So I hope the same for, uh, our listeners and members.

Speaker C: Thank you so much. It was an honor to get to come on and talk about my journey and share and I hope it's been helpful to folks. So thank you for having me.

Speaker A: Thank you for listening to this episode of Sheas Unplugged. I hope it inspired you in your personal journey. If you enjoyed listening, please subscribe and share this episode with others. You can find out more about Sheas at our website, sheas.org you can also find us on LinkedIn.