National Women's Small Business Month: Female Entrepreneurship in Finance

In this episode, Virginia Heyburn is joined by Engage fi’s Co-founder & CEO, Jenn Addabbo, to celebrate National Women's Small Business Month. They discuss Jenn’s journey to entrepreneurship, female leadership in a male dominated industry, the unique strengths women bring to the table, and how today’s leaders can support and mentor the next generation of female trailblazers.

Transcript

Virginia Heyburn (00:02.116) 

Hello everyone and welcome back to another episode of FinTech Unleashed. My name is Virginia Habern. I'm the Director of Research, Insights and Advocacy at EngageFI. Did you know that October is National Women's Small Business Month? It's a time to recognize and celebrate the tremendous contributions that women leaders make in business and entrepreneurship. And at EngageFI, we are so fortunate that our leader is Jen Adabo. Jen is the co-founder and CEO of EngageFI. 

She is with us today. And before I bring Jen on, Jen has several impressive recognitions that I want to brag about a little bit because she might not. She's a 2023 Businesswoman of the Year from Tampa Bay Business Journal. She's in the Ernst & Young Winning Women Class of 2022. She's also a 2019 40 Under 40 recognized by Tampa Bay Business Journal. And under Jen's leadership, EngageFI has been recognized. 

as an Inc 5000, fastest growing private companies, four years in a row, and Tampa Bay fastest 50 companies, three years in a row. So I'm so excited for you to get to know Jen, to hear her incredible journey through starting EngageFI and also leading EngageFI to the success that we enjoy today. We'll talk about what it means to be a woman leader in a traditionally male led industry, what unique strengths that women leaders bring to business. 

and also how today's leaders can support and build a future generation of women in leadership. So let's get right to it. 

Virginia Heyburn (01:37.72) 

Jen, I am so thrilled to have you on the podcast today. Welcome. 

Jennifer Addabbo (01:41.559) 

Thanks, Virginia. I always love talking with you. Appreciate it. 

Virginia Heyburn (01:44.664) 

Always fun. So Jen, when we thought about who to bring on to talk about this topic in October, of course we come to you. Your story is so inspiring, it's motivating, certainly to all of us at EngageFI. Tell everybody out there, tell us about your journey through the early stages of startup because your story is pretty incredible. 

Jennifer Addabbo (02:06.849) 

Yeah, it's so funny. Sometimes we don't take the time to look back until we have these opportunities to have the discussion. So it's still shocking to me that we started this company 10 years ago on a leap of faith, honestly, and really with a passion to help the community financial institution market. Backing up a little bit, I had spent my career as a vendor like you, a lot of similarities in our background. 

spent a lot of time at FIS and then went to a credit union service organization, PSCU, that's now Valera. And, you know, even as a kind of learning woman and female in financial services and fintech, I was always kind of keeping my eyes open to what the next opportunity was and was always very competitive with myself in trying to kind of challenge myself to a zone of complete uncomfortableness and really try to get better every day. so 

Part of that was really the spark of starting this consulting firm because I had been a vendor for so long in negotiating against a lot of my competitors, many of whom happened to be male counterparts, but felt like there was another way for us to approach the market, have a really focused, passionate team that cared about the financial institution first and foremost and that 

If we treated our clients well and if we treated our team well, then the growth would happen. And now here we are, fast forward 10 years, and I'm just humbled by the growth that we've seen, the level of talent that we've been able to bring to this organization. So it's a great opportunity to reflect back on where we were. When I started the company, I was pregnant with my second son. 

My parents for sure thought we were crazy. My husband had started a small business here in Tampa and just fingers crossed said there's only one way this thing can go. And thankfully we're now 10 years forward and it has been working out. 

Virginia Heyburn (04:15.354) 

That's wonderful. mean, just to think about starting a business while you're growing a family, that's certainly a very challenging way to do it, but it has, of course, ended well. So that's a beautiful thing. Now, your experience was obviously unique. You talked about that. How did it shape your thinking about leadership? How you lead, engage, FI? What is it that you think you've taken from? What was... 

I think most people would say was a challenging way to grow a business. 

Jennifer Addabbo (04:48.973) 

Yeah, I would say I learned throughout my career on sort of wild extremes of leaders. So when I think of the probably folks that had the biggest impact on me were the folks that I did not want to be anything like from a leadership perspective, from a, you know, just sort of, this is how you're going to get things done and it's going to be my way and you have to follow my lead because I'm all knowing. I had some folks that led me in that way. 

early on in my career. And then I had wild extremes of very caring leaders that I feel like are true family and friends still to this day, 20 years later. So I have throughout my career reflected on how I felt as a person being around those two distinct types of leadership qualities. And I think you will agree that I do tend to lean toward, you know, 

treating the folks that I get to work with as a family. And that might be a little bit different than if a traditional sort of male CEO was running the organization. I don't know. I've had the luxury of co-founding with James Guild, who I consider family, and to be able to work alongside Andres now, it's really been eye-opening for me to surround myself with supportive male leaders as well to kind of bounce off of, right? So that you have, play to their strengths. 

in areas where you are self-aware enough to know that you have blind spots. And I think that's been very helpful too, is just putting people around me that are smarter and have tremendous expertise and that I can just kind of help steer the ship where we need to. 

Virginia Heyburn (06:33.046) 

And self-awareness is such an important business attribute. And you did mention, you know, I might perceive it. Certainly being here two years, it's good to know that someone has your back when you come to work every day. And I think that inspires loyalty so that I have your back and we have everyone else's back. It truly is a family. Now, speaking to the culture, tell us about the culture that you've built and engage up by. You know, I know it's 

obviously very supportive, but if you could give some details on what that really looks like on a day-to-day basis, that would be great. 

Jennifer Addabbo (07:07.651) 

Yeah, I mean, when you say supportive, that, one of our core values is people champion. And naturally I'm a pretty transparent person. You know, people know a lot about my personal life, my personal goals and my professional goals for this organization to keep it growing. And I think that even when I'm interviewing people or when we have new hires that come on board. 

I'm completely transparent. think that sometimes they're probably a little bit surprised. And my intention there is that I want to make sure they know I'm here. I'm here to help however possible. I'm eyes wide open to new ideas. And especially as people join our team, they come in with fresh, a fresh mindset. And so the culture has been built from that. I think at its core, which is continuous improvement is another one of our core values. And we, we really, 

focus a lot on that in the interview process, in the onboarding process. We do a lot of work with Predictive Index ahead of interviewing so that we are hand selecting the right people to bring into this group. And what ends up happening is good people bring good people and that just makes the entire organization better. 

Even our interactions on teams that we see all day, every day and late into the night and celebratory things that are happening personally or challenging things that might be, somebody might be going through personally. This team really rises to the occasion to support each other. And it's, I wish I could say it's something that I did specifically, but I do think it's just creating an environment where people have an opportunity to support each other and, and appreciate each other. that's. 

that's core to who we are as a team. 

Virginia Heyburn (08:53.88) 

Yes, it's from my experience, you just feel the empathy in the organization, but at the same time, it's empathy with the willingness absolutely to make those hard decisions and really in your shoes be the business leader that drives the company forward. 

Jennifer Addabbo (09:10.369) 

Yeah, and I think, you know, competitiveness is one of my probably strongest short personality attributes. Yeah, I know, shocking. And it's truly, honestly, it's with myself, right? So, and when I see kind of how that spurs people to be better, I think that's another component of, we have the hardest working team of people that I've ever seen, that I've ever been able to work around and. 

Virginia Heyburn (09:16.66) 

No. 

Jennifer Addabbo (09:35.203) 

When you're seeing people work really hard, you want to work even harder because you want to support whatever they're trying to accomplish. And so that's another component of our culture that it is, we're very celebratory, we're very supportive, but at the end of the day, man, the team works hard and the clients are raving fans because of it and Clients4Life, which is awesome. 

Virginia Heyburn (09:56.066) 

And I think that's what's so distinctive. It's not just that it's a great place for us to come to work. It is a great outcome for the clients too. Because everybody's all in. 

Jennifer Addabbo (10:04.673) 

Right, right? Exactly, exactly. 

Virginia Heyburn (10:09.59) 

So speaking of competition, you did bring it up. We obviously in financial services consulting and the financial services industry in general, we operate in what's traditionally been a male-led, male-dominated industry. You and I have both experienced that over a long period of time. And your leadership here at EngageFI is different. You've described that. But with more and more women leaders coming into financial services, coming into leadership positions in 

financial services of credit unions, banks, fintechs, you name it. How does EngageFI contribute to and really support that changing representation of women in our industry? 

Jennifer Addabbo (10:51.115) 

Yeah, it's been great to see even in some of the financial institutions, the larger financial institutions to see women taking the reins and really sort of bucking the trend. mean, we're lucky enough. have, you know, 70 % of our organization is female, 90 % of our senior leadership is female. So I might be slightly biased to that and the success that that can bring. But we do, we've done some great podcasts, as you know, with some of our clients. 

better female leaders to sort of get some understanding of the nuances of people's careers and how they got to that leadership role. We do a lot of work within our trade, within the industry to support next generation of leaders coming up. I just was working with a high school here locally who is creating this digital divas strategy to try to encourage women. 

young women to consider the technology as a field and not think of it as just, I'm to have to go be a developer or coder. And so I was shining a light for them on, know, FinTech and financial services in general and data and AI and all of the areas that we're focusing on and continue to invest in as opportunities for them to, you know, hopefully provide alternatives. So it's really big for me to, to who much is given, much is expected. And I 

try as much as possible to provide sort of a sounding board. I think sometimes as women, it's probably harder for us to talk about what's made us successful. And sometimes you just take for granted that, yeah, it just worked really hard and got here. So I think I'm learning to sort of pinpoint areas within my career that I can reflect on and hopefully help others that have a desire to start a business. 

and or to sort of move to that next level in their career. think I can think of friends personally who were somewhat just kind of concerned in their own mind of their self-worth of what their ability would be to take that next leap in leadership instead of seeing what folks outside might see in them. So I think that's a trend I'd like to see changed within female leaders and folks that want to challenge themselves to go to the next level. I think our 

Jennifer Addabbo (13:16.257) 

male counterparts sometimes think a little more highly of themselves than they might actually deliver on. But for the most part, think women tend to struggle with that. maybe we don't raise our hand to take as many opportunities or take that leap of faith, you know, like starting a business for fear that we might fail. So that's kind of a trend that I'm hoping to try to instill in the next generation female leaders. 

Virginia Heyburn (13:40.76) 

I love that. So risk taker, you're hard charging, you're supportive, you're very understanding of everybody who works at EngageFY and by extension of all of our clients and I think that really shows in what we do day in and day out. 

Jennifer Addabbo (13:56.213) 

It's most important. I if we take care of each other and we take care of our clients and the rest is easy, that's what I love about what we do. It's an easy gig when you've got the right people around you. 

Virginia Heyburn (14:06.488) 

I will leave it at that. That is the best way to close this podcast. Jen, thank you so much. And by the way, your dress is fabulous and it co-coordinates with the picture in the background. 

Jennifer Addabbo (14:07.767) 

Yeah 

Jennifer Addabbo (14:13.571) 

Thank you. Thank you. Little fall colors for us. 

Virginia Heyburn (14:19.318) 

I love it. Wonderful. Thank you so much. And for everybody out there listening in today. We are always so pleased to see you in our podcast audience. Thank you for listening to today's episode. To stay informed on when we're going to be dropping the next episode, follow EngageFI on LinkedIn. I look forward to seeing you again on the next episode of FinTech Unleashed. Have a great rest of your day. 

Jennifer Addabbo (14:22.359) 

Thanks for your time.