Trista Engel, CEO, Paragon Legal

Jessica Markowitz, President & COO, Paragon Legal

Paragon Legal is a women-founded and women-led business that provides high-level interim attorney support for in-house legal departments.

While Paragon is a well-known leader in a rapidly growing field, many don’t know that its co-leaders represent the first female search fund partnership to acquire a U.S. business. 

Here, Paragon’s President & COO, Jessica Markowitz, and CEO, Trista Engel, weigh in on this distinction in a conversation with Gwendolyn Guerra, Paragon’s Director of Operations.  

They also discuss working on Wall Street during the Financial Crisis, how the business world should be adapting to today’s market forces, and what their interests are outside of work (spoiler alert: pickleball is involved.)

Can you talk about your background and career progression? 

Trista: I grew up in Washington, D.C., and went to Yale for college, where I spent a lot of time playing soccer and not a lot of time thinking about what I wanted to do with my life and career. Coming out of college, I felt like my choices were to go to medical school, law school, or Wall Street, and, by process of elimination, I chose Wall Street. 

My first job out of college was with Credit Suisse, and my first day on the desk in 2007 was also the first wave of layoffs of the financial crisis. It was a very tough time to start a career on Wall Street, but it was also an interesting time to be there. I learned a ton, but I quickly figured out it wasn’t the right job for me.

I moved to a very small communications consultancy that was a much more qualitative and strategic role. From there, I went to the University of Chicago for business school, where I met Jess. 

While in business school, I wanted to find something that had the best of both of my previous roles. I wanted something that was data-driven and analytical but also had that qualitative and strategic element, so I went to Bain & Company in a management consulting role. I valued my time and learned a tremendous amount in my three years there. I loved the strategy, the teamwork, and the problem-solving, but I also felt like there were missing elements, things that I really wanted for my career. 

Jess and I had long talked about how we could run a business together. 

When we came across the search fund model, it all clicked for me. 

It seemed like a fit in terms of what I was looking for in my next move and a partnership with Jess. After many weekend days spent at Starbucks, considering all the angles of taking this leap, we started Calyx Capital Partners, which brought us to Paragon.

Jessica: I grew up on the East Coast, went to school at Tulane in New Orleans, and then worked in finance at Lehman Brothers. It was a very interesting time to work there during the Financial Crisis. I didn’t know what was normal and what wasn’t. 

In hindsight, a lot of things were not normal, but it was my first job. Lehman’s fallout led me to the Royal Bank of Scotland, working on the trading desk in distressed credit. I quickly realized it wasn’t a fit for me. I wanted to get inside companies, understand how they worked, and how to make them better.

I went to the University of Chicago, where I met Trista. After business school, I did distressed turnaround and restructuring consulting, where I helped troubled companies fix themselves through operational and balance sheet improvements. I understood how to create value in this role, and I loved it. 

But, similar to Trista and her role at Bain, many things were missing for me. When I learned about the search fund model and the opportunity to raise capital to acquire a business, it immediately clicked for me as well. I’m just so lucky that the timing and our lives were at a point where it worked for us to do this together.

What led you to Paragon?

Jessica: Well, a dirt road and Belgium… 

Trista: Rural Belgium…

Jessica: Rural Belgium. Yes. A lot of things led us to Paragon. It was very fortuitous. We were looking to buy a business where we could add value and be a part of the team for the long term. We connected with Mae O’Malley, Paragon’s founder, about six months into that 25-month journey. 

We liked the industry. We liked what we had heard about Paragon, and we thought it was really compelling. 

Mae told us: “I love what you guys are doing, but I’m not interested in selling Paragon. Best of luck.” So we went on our merry way but stayed in touch. 

About a year later, Mae reached out and said: “Okay, I’m ready, and I think you are the right people to take on my business.” And the rest is history.

Mae, at the time, was living in Taiwan, running a business in San Francisco, and Trista and I were living in Chicago, so it was a whirlwind to try to meet in person. 

We finally did a due diligence week in Belgium, where Mae was staying at some sort of waterpark-like resort. It had goats — a petting zoo — in the middle of absolutely nowhere. 

Trista: When we started Calyx, we were looking for a business in an industry that excited us and had a lot of tailwinds, a proven business that was running well with a solid foundation. But also a business where our skill sets could be of value. A business with a great culture that we would be excited to be a part of and proud to continue. 

Over those 25 months searching for this unicorn of a business, we reached out to probably 10,000 companies and talked to hundreds of business owners. We visited a number of business owners.

We were looking for a needle in a haystack that fit the two of us. 

When we met Mae for the first time, five months into our search, many things clicked, but an important element was that she was having fun. She wasn’t ready to sell at that point. 

We respected that and understood that when you’ve founded your own business, it’s your baby, and it’s not easy to move on from that. We kept looking, all while keeping in touch with Mae and thinking about Paragon. 

So when she came back and said, “Now feels like the right time for me,” it clicked on both sides. 

We definitely found what we were looking for — an industry that was growing and that we were excited about, a company that was strong but where our skill sets could add value in a new way, and a company that had a really great culture that we were excited about.

I think, from Mae’s perspective, she’d been approached by several private equity funds and competitors about acquiring Paragon, but nothing felt right to her before we met. 

She was excited about passing the business on to two women. She also understood that we saw the business’s potential and wanted to be the ones to unlock it. 

Mae saw that we valued the team and culture, and there were many elements we were excited to continue. She knew we would not just come in, chop things up, and change them around. I think we all feel lucky to have met one another.

Trista briefly mentioned the word ‘search fund.’ You and Jessica had a pretty amazing experience in that world. Can you talk a little bit about that?

Trista: A search fund is a type of investment fund for a would-be business owner or entrepreneur to search for and then acquire a company. 

For us, it allowed us to be in a situation where we could spend some time searching for a great business with the backing of a group of really thoughtful and committed investors. Our investors supported us along our journey, understood our motivations and skill sets, and saw the value of finding a great “needle in the haystack” business with an owner looking for a transition plan. 

The investors in our search fund then did a follow-on investment to acquire the business, and, over the past four years, they have remained a strong support network and board network.

Jessica: As does Mae.

Trista: Jess and I, as far as we’ve been told and as far as we know, are the first female search partnership in the United States and the first female search partnership to acquire a business in the United States, which is an exciting achievement for us. 

Like many financial or investing fields, there are not a lot of women in the search fund space. 

That’s certainly changing, but when raising our search fund over six years ago, it was a different environment. We were asked, “Why do you think you can be successful at this when no woman has been successful at this before?” 

And when we were making the rounds to learn about search funds, to learn about the process, to build an investor network, to build a support network, there weren’t a lot of women for us to turn to.

The reality is very few women have tried this before. And, of course, if you don’t see people who look like you doing what you’re trying to do, it makes you wonder if there’s a reason, making it a little bit harder to visualize yourself in that position. 

We got many questions about it, but we were very determined. We were very confident and had thought through what we wanted to do and why. 

Over the last six years, we’ve spent a lot of time helping to build up the community of women in the search field and supporting other women coming up and trying to do what we did. Several other female partnerships are out there searching and acquiring businesses, which is really exciting.

Jessica: There was one woman-run search fund in Brazil a few months before us — not a partnership — that bought a business, and then there was us in the United States.

What values drive you in your work and your life?

Jessica: A lot of the values that drive me are the values that we have at Paragon, which is really convenient because it’s easy to live by them. We call it “do the right thing, even when it’s hard” — acting with integrity in any situation. 

Taking the long-term view and having solid principles are important to me.

Aside from values —  I like having fun at work, getting to know my team, and being myself. A place where you can debate openly and have what may, on the outside, look like arguments, but between Trista and me, it’s just conversation to get to a better place. I call it positive conflict.

Trista: I would agree with that. One of the things that drew us to Paragon was the values. They were not explicitly written, but we could see and feel them from talking to you, Gwendolyn, and the other folks who were at the company when we joined.

We’ve gone through the journey over the last few years of writing down and explicitly saying our values, refining them, and putting new words to them. They’ve always sort of remained the same and very similar to what Jess and I discussed six years ago — when we decided to go into this partnership long before we knew about Paragon. 

Finding challenge in your every day is important to me, and we have a value related to that at Paragon — seeking to understand and grow, which is about learning and being open-minded. 

I care about people and relationships — one of our core values has always been people first. We have a very long-term relationship focus at Paragon. 

I need balance in my life. I care about and prioritize my family. I care about being able to play soccer. I care about having flexibility and ensuring that all parts of my life are taken care of. That includes, like Jess said, having fun and being able to be who you are at work.

Can you name specific challenges and rewards to leading a company?

Jessica: I think it’s been a really tough four years. Not Paragon specific — I think in the world, it’s been a heavy load for any individual. 

Leading a business through these unprecedented times has been challenging. I just want “precedented” times for a minute! 

We haven’t found a book or course, or class or advisor that you can go to that could say: “This is how you get through a pandemic, and this is how you get through whatever the United States is going through. And this is how you get through things that have never happened.” 

It’s been a challenge because we’ve had to learn, and we’ve made mistakes along the way. So not only are we growing into our roles as leaders at Paragon, but we’re doing it through a time that just feels incredibly heavy. 

It’s challenging to manage people through that. At the same time, it’s been amazing to watch people on the team, bringing them onto the team and then watch them grow, learn and develop and accomplish things they didn’t think were possible. That is amazing too.

Trista: I totally agree. When I think about the rewards and challenges, it’s all about the people. Coming from a consulting role, you’re often looking at and solving problems. You’re thinking about the business issues, and it’s very analytical, and there’s maybe not always an answer, but there’s kind of a clear path or a way to solve the problem. 

When you step into a leadership role in a business, it becomes all about the people; it’s no longer about day-to-day problem-solving, it’s just about how you interact with and care for people. To Jess’s point, there have been a lot of really, really difficult moments over the last four years. There have been a lot of really difficult moments in the last two weeks. It does feel unprecedented, and the biggest challenge is feeling responsible for the people you care about.

It impacts everything we do and say, whether it’s a business decision or supporting the team through all of these crazy global, national, or even personal challenges. You feel that weight, and you can’t go home at the end of the day and forget about it. It’s very real. But the positive part is that we have such a great team that truly cares about one another, and we help each other along. And that’s the biggest reward. 

Diversity has been one of Paragon’s core values probably since the beginning of the company, and as the leaders of the organization, what does DEI mean to you, and how do you embed it into a company culture?

Trista: When I think about what DEI means, it means being open and welcoming to all views and perspectives and creating space to listen to and amplify those voices. It’s very challenging to know how to embed it into company culture, but it’s always been a part of Paragon’s culture. 

As one of our values, it comes naturally to the business, but we still have to work on it. You have to keep talking about it and put resources into it. Money, yes, but also time and energy. 

You need processes that keep you honest about your efforts, the results, and where you’re trying to go. 

You have to make it part of everyone’s responsibility if it’s truly going to be a part of the company culture, and we still have more to do.

Jessica: It’s been a journey to figure out how to ensure that we are doing it in the best way we can. And there’s a learning process to us even though it’s been something core to Paragon since its founding 17 years ago. 

Creating the space for DEI to be more than just foundational, but putting actions and words behind it and building a program behind it has been something we’ve done over the last couple of years. We’re learning, and we’re making mistakes, and we’re trying to figure out how to do it right. And I don’t even know if there is a right, but we’re trying.

What business trends do you think will be important in the next 12 months?

Jessica: That is a tough one because so many things impact the world from a macro perspective. Layoffs and cost pressure in this uncertain economic landscape. Significant interest rate increases from the Feds that drastically impact investor allocations across the United States and even the world. You still have the globe choked up a little with supply chain issues from COVID. There are a lot of issues within the labor pool, both in the United States and internationally. I could go on for a very long time about all the problems in the world.

But I just listed a few of the big ones because what’s important over the next 12 months depends on how many of those things shake out. A couple of things that are evident that I don’t think will shift back are employees demanding more flexibility over “where, how, and when” they work. Being able to support the Paragon team and being an advocate for that will be continued. And we’ll also continue to see companies open to remote work.

Trista: I hope stakeholder capitalism over shareholder capitalism continues. Where companies, by employee demand and hopefully by the goodness of their hearts, continue to value speaking up about societal issues and allowing their employees flexibility. 

Where companies do the right thing for their employees, whether that is in regards to healthcare or parental leave or all sorts of things.

Companies are starting to step up and think about what’s right for the world and best for their employees instead of focusing on profits alone. 

Related to the rebalancing, I believe companies are focusing on spending money wisely, thoughtfully, and efficiently, rather than profligately, because there has been a glut of capital with nowhere to go. 

So I think that many companies will be rethinking how they make spending decisions and allocate dollars, which will be important.

Turning back to both of you individually, what are you most passionate about both in and outside of work?

Jessica: I love seeing people grow within work, and I’m passionate about helping support them. 

Outside of work, to be perfectly honest, I’m figuring out how to find that balance to find more passion in my personal life. I will take figuring that out as my new passion for this year.

Trista: And pickleball!

Jessica: Yes. Yes, exactly.

Trista: At work, I think a lot about our company culture and Paragon being a place where people want to work and feel cared for and where there is a culture of trust and collaboration. I love seeing the results; I’m competitive and want us to do well. 

I know this company’s going to the moon. I have big dreams for Paragon. But I feel strongly about doing that in a way that allows us to build on our company culture and be a place that people want to work and are proud to be a part of. 

In my personal life, I have a 3 year old and a 5 year old. That is where the majority of my time gets taken up. 

I do feel strongly about the balance piece for myself. So when I turn off my computer on Friday, I am pretty good about compartmentalizing and keeping it off. But I try to focus on being with my family when I’m with my family and being focused on work when I’m at work. That balance is important to me. 

I recently started playing soccer again, which has been fun and exciting and is something I’m somewhat reinvigorating my passion for.

What are you most excited about for the future?

Trista: I’m excited to continue building our corporate team, which means adding new people, giving the current team new growth opportunities, and giving everybody on our team new challenges —  pushing them outside of their comfort zone, learning new things, and putting their fingerprint on Paragon and Paragon’s trajectory, which I think is super exciting. 

Growth means providing more opportunities for attorneys and clients to do work in a way that works for them — finding that balance and finding that cost efficiency. The right way [for them] may not be the traditional way, but it is the way of getting the work done — doing challenging work in a way that fits their lives, so they can find that balance that I feel so strongly about.

Jessica: I am excited to see people in person more often. I was probably the best “staunch, never work remote” person pre-pandemic. 

Now I like it a lot, but I want to make it more regular to see folks on the corporate team and attorney team, meet with clients in a more regular cadence, and just get back out there in the world. It feels like it’s been too long. I’m excited about that.

What is your favorite vacation spot?

Trista: India is one of the most interesting places I’ve been and one of the places I’m most excited to take my kids. My dad is from India. He grew up there. He still has family there. 

When I was a kid, we used to go every two years. So I have many memories of visiting my grandparents in their apartment, eating delicious Indian food, and watching the lizards climb on the walls in the middle of the night. 

It’s one of the most unique places I’ve been to, with vibrant culture, delicious food, and family history. I don’t know if it’s my favorite vacation spot if I’m thinking of palm trees and beaches, but it’s a place that I feel connected to and a place I’m excited to take my kids someday.

Jessica: Mine isn’t a vacation spot, either. I haven’t lived near my family in 20 years. I get excited about having coffee outside with my brother, his wife, and nephews at their home. My mom and my other brother come along as well. It’s a nice treat on the weekends until it gets a little bit too chaotic with the kids.