As a former athlete, Annie Morsches Bailey knows what it takes to make it on the field, but now as the COO of RISE, a sports-focused family office, she’s teaching players what it takes to make it off the field. The sports executive helps her clients on how to plan for their lives beyond sports through avenues such as philanthropy, sitting on boards, and having more ownership over their careers.
As a woman in a high-powered position, Annie has used her expertise to elevate RISE. Becoming partner and COO in 2024, Annie oversees internal operations, culture, and compliance while working with both established and newly drafted athletes as they navigate contracts, endorsement income, and long-term financial decisions. Her work focuses on how athletes actually utilize their money. As a mother of two, Annie hopes to show her sons that she can be a strong mother while pursuing her career. She talks with Her Agenda about her evolution in sports.
Her Agenda: As a former Division I athlete, how has that background helped you as a sports executive?
Annie Morsches Bailey: Growing up in sports and then being a Division I athlete in college, you have to learn how to be organized and how to be able to put things in a priority to make sure you’re getting what you need to get done. You’re balancing sometimes four or five hours a day of practice, and then having to go to class afterwards, and having to get your study hours in. From a young age, I learned how to prioritize what was really important and have the ability to stay organized and on the right path to get done what I needed to get done.
Her Agenda: What made you pivot from athlete to executive?
Annie Morsches Bailey: As a lacrosse player, there’s not really much trajectory after college. It’s not really a money-making sport. There’s actually a professional league now for women, but that wasn’t around when I was in college. I also struggled with injuries throughout my whole career in college. I started seeing the writing on the wall that sports were coming to an end, and it was time to focus on what my life was going to look like after college. And so I come from a family of family businesses. My brother will be the fifth generation in our family business. My grandfather also operates a business. I always understood that work was going to come, and how to work hard, and what was required. I interned my senior year with Michael Ledo, who is the CEO and founder of RISE, as his executive assistant at his previous company, which was a training facility for athletes. It was my start to get my feet wet in the business world, and the rest is history. He and I hit it off, and it’s been 12 years now that we’ve worked together.
Her Agenda: How has working in this business empowered you, and how do you empower your clients?
Annie Morsches Bailey: It’s been very empowering. I was one of those people who never really knew what I wanted to do. I didn’t really like school. It wasn’t my thing. I didn’t have a job that I always wanted. I jumped from major to major. When I started working with Michael, I found I really enjoyed working with other athletes from that background and being able to relate to them in that way.
Number one, my confidence has come a long way. I struggled with confidence in college, and having a lot of injuries. I worked my way up, starting from a client relations specialist to now being a partner in the COO, and finding what works for me, what my passions are, how I can impact other people through that, and relating to my clients. Having the athletic background and finding one thing that we have in common and then pulling that out of them and really helping them identify who they are outside of sports has been something that’s really become a passion of mine throughout the years.
Her Agenda: Being a woman in a high position in a male-dominated field, how have you persevered, and what are some challenges you have faced?
Annie Morsches Bailey: It’s definitely a male-dominated field. I think it’s come a long way, even since I started. Women are leaving their mark and being trailblazers for women who want to get into sports in the future. You walk into a room, or you walk into a meeting, and you’re the only woman in the room. It can be really intimidating, especially when you’re just starting your career. I’ve been really lucky that Michael has been someone who’s always valued women, and he sees them as true equals and sees how they can impact a business or impact others. He has always been a huge advocate for me. Sometimes it’s really hard not to let your voice shake when you’re in a room full of men and have the confidence, especially if they’re all older than you or have more experience than you. I think never letting my voice shake, knowing I’ve earned a seat at the table, just like they have, and just continuing to speak up for what I believe in and what I know is right. I just know my worth, I know that I’ve earned every right to sit in the room, just like they have.
Her Agenda: What is the most rewarding moment you’ve had while doing this job?
Annie Morsches Bailey: The relationships that we’ve built with the clients, and that I’ve built specifically. We’ve got a couple of guys who have been our clients since the very beginning, and they’re like family now. Being able to see them from where they started in their business life, and also just as humans fresh out of college, and don’t know what they want to do outside of the sport. Now they’re really successful on the field, but also with the sport of RISE, they’re really successful off the field, too. They’re starting businesses, and they’re sitting on boards, and they’re running amazing philanthropy. That is definitely the most rewarding because not only have I been with them through that journey, but I’m just able to witness it and take a step back and see how amazing these athletes are. Not everyone sees them as humans. A lot of people just look at them as athletes and don’t think anything else of them. Seeing their goals, dreams, and visions come to life for their businesses is awesome.
Her Agenda: Tell me about your role at RISE and what you like most about working at the company?
Annie Morsches Bailey: When I first started at RISE, I started in the client services role. I was helping with anything off the field, the execution of those things. When we were doing strategy sessions and goal creation, it would then come to me to make sure that all of those things were actually getting done. I’ve transitioned out of that, and now I serve as the chief operating officer. I’m running the day-to-day operations of Rise as a business. I also oversee all of our staff, specifically our lifestyle management team, our investment and finance team, and our recruiting team, and support them so that they can help our families sustain and build their wealth. The most fulfilling part of that now is being able to have my hands in a little bit of everything and have a global oversight of all of the different things that are going on for our clients. Each one of them we view as a blank slate. They’re their own person. They have their customized plan that we create for them. Being able to not be so much in the weeds, but help from a leadership style role and keep RISE moving as a business so that everyone else can operate externally is really rewarding, and I didn’t necessarily know it would be as rewarding as it is now.
Her Agenda: What have you learned working on the business side?
Annie Morsches Bailey: A lot of things. I wasn’t a business major. I didn’t have a lot of business experience aside from watching my dad run a company and my grandpa. I’ve always been around it, but not in it. I see what it truly takes to operate a business: the budgeting, the hiring, and the culture. Culture is huge because we maintain a strong culture for our employees, and make sure everyone always feels heard, and they are getting the leadership that they need so that they can keep growing. I think that’s been really great.
Her Agenda: What kind of advice would you give another young woman wanting to break into this field?
Annie Morsches Bailey: Don’t be afraid to try something that you don’t think you’re going to like. When you’re getting into the sports industry specifically, there are a lot of jobs that will help you get to where you want to go. That may not be the end goal, but sometimes it takes starting small and building your way up. So, you know, don’t be afraid to try different things. It’s okay if you don’t like them, but that’s going to help you get to where you want to go in the end. You have to be confident and not let your voice shake when walking into a room. And like I said, just knowing that you deserve to be there just like everyone else does and that you provide a value that no one else can. You just need to, even if you’re nervous or scared, put on a good face, look good, feel good, and go out and do it.
Her Agenda: When you’re working with your clients, what do you aim to teach them about the sports world?
Annie Morsches Bailey: They know the sports world. That’s their whole life. Our goal is to teach them about the business world and help them find their identity outside of that sport. Whether they want to own and operate franchises, focus on philanthropy, or be the best patriarch or matriarch. We’re trying to help them be ready for when the sport ends because it’s not forever, especially football, which is primarily what we work with right now. It can end very abruptly with an injury or getting cut. We’re trying to expose them to the business world and educate them. Education is a huge part of that. We want them to be able to stand on their own two feet and understand how to read a P&L and the intricacies that go into that. We want them to fully understand that and know that they’re so much more than their sport. We also want them to know that their mental health is important. We’re just trying to teach them and empower them to build and sustain their wealth within business so that they know their world is just beginning when their sport comes to an end.
Her Agenda: What key qualities does someone need to sustain themselves in this business, and why?
Annie Morsches Bailey: I think you have to be fearless. I think you have to be flexible. Every day looks very different. Athlete schedules are crazy. You have to be able to be flexible and confident. You have to be a good communicator and understand that every single athlete comes from a different background, and that’s not going to look the same as yours. You have to build the bridge between business and where they are. Communication is huge.
Her Agenda: What new heights do you want to aim for as your career continues?
Annie Bailey: I think because I’m young and I serve in a relatively high position, I want to keep growing myself. I know there’s a lot that I don’t know, and a lot of experiences that I haven’t had yet, so I’m always trying to better myself and help elevate the team through horizontal leadership rather than vertical leadership. They know that I’m willing to get my hands dirty with them and do whatever’s needed to get us where we need to go. Now that I’m a mother and I have two kids, it’s a balancing act being present in motherhood and also being a force to be reckoned with in your career. I want my boys to grow up seeing me as someone who was well respected and was always working hard to give them the future that I would love for them to have. I want to continue to elevate RISE and continue growing RISE, but also I want my kids to grow up seeing a strong mother who tried to be a very good mother for them, but also still fulfilling myself as well.
[Editor’s note: This article has been edited for length and clarity.]
