Rebekah Brown Olson didn’t plan to lead a state CPA society. A single leadership assessment during a firm training session reframed how she saw her own strengths, and thirteen years later she’s the CEO of the Maryland Association of CPAs, connecting firm leaders across the profession every day. In this conversation, Brannon Poe talks with Rebekah about what’s really driving change in accounting right now, and why she believes community, not information, is what separates firms that thrive from firms that struggle.
Rebekah shares an encouraging read on the student pipeline, pointing to strong turnout and impressive second-career candidates at a recent University of Maryland accounting graduation event. She also walks through her theory on where private equity is headed: a barbell shaped profession, with large firms formed through consolidation on one end and a new wave of small, independent firms on the other, as CPAs who leave newly acquired environments choose to build something of their own.
For firm owners thinking about their own exit, Rebekah’s advice centers on two habits: treating strategy as something to revisit constantly rather than a plan that sits on a shelf, and involving the people around you early, since real alignment comes from letting your team weigh in on where the firm is headed.
The Conversation Covers:
- How a leadership assessment redirected Rebekah’s entire career path
- Why community may be the biggest differentiator for CPA firms over the next decade
- How private equity could reshape the profession into a barbell shaped structure
- Why small firms are positioned to specialize and move faster than larger competitors
- How involving your team early creates real strategic alignment ahead of a transition
- Why choosing the right private equity partner matters more than the deal itself
Rebekah closes with a story from her college years at Ohio State, working as a football field manager during a live scrimmage, that ties back to the same theme running through the whole conversation: what it looks like when a community shows up for someone.
This Episode Is For:
- Firm owners curious about how community and connection shape long-term success
- Leaders ready to think through a 5 to 10 year exit and succession plan
- Practitioners wondering how private equity might change hiring, retention, and culture
- Anyone interested in how small firms can compete through specialization and speed
BOOK RECOMMENDATION
The Upside of Stress: Why Stress Is Good for You, and How to Get Good at It by Dr. Kelly McGonigal
TIMESTAMPS
00:00 – Brannon Poe intro and podcast welcome
00:14 – Introducing Rebekah Brown Olson, CEO of the Maryland Association of CPAs
00:57 – How a quarter-life crisis and a leadership assessment changed Rebekah’s career path
01:41 – From CPA firm senior to curriculum developer at the Maryland Association of CPAs
03:12 – Working part time, then full time, then becoming CEO three years ago
04:02 – What Brannon and Rebekah share: burning out of public practice and finding a better fit
04:45 – What Rebekah gets to do now: advocate for the profession and connect people across it
05:06 – The big picture view: what the Maryland Association of CPAs CEO is seeing right now
05:31 – Why getting good at change is the most important capability for any accounting firm
06:00 – Why community is the competitive advantage when complexity and change accelerate
06:34 – Why you can’t know everything but you can know a lot of people
07:19 – Recruiting new students: are the numbers moving and what kind of students are coming in
08:15 – Why the pipeline alarm is starting to work and what recent graduation events are showing
08:40 – Accounting as a stable major during economic uncertainty
09:07 – What the new wave of accounting students looks like: different backgrounds, strong leaders
09:30 – Retention: are people staying in the profession better than they used to?
10:01 – The historical reality of planned attrition in CPA firm hiring
10:45 – The move from public to private still happens but may be slowing
11:10 – Brannon’s theory on PE-driven salary increases and the poaching risk that comes with it
11:37 – Why starting salaries in accounting need to keep rising to compete for talent
12:00 – How private equity is creating a barbell-shaped profession
12:40 – What the disappearance of the midsize CPA firm looks like and why it matters
13:29 – How small firms can win through specialization and speed on technology
14:25 – What Rebekah would tell a CPA firm owner who is 5 to 10 years from an exit
15:17 – Why a 5 to 10 year plan has to be iterative, not static
15:43 – Involving your team in strategy: why it changes buy-in, retention, and execution
16:08 – The Business Learning Institute and working with small to midsize firms on strategy
16:32 – Why the best insight sometimes comes from the person scheduling client appointments
17:53 – Vision casting as a retention tool: why people stay when they know where the firm is going
18:45 – What happens when someone is not bought in: it’s okay, not every culture fits every person
18:56 – What Maryland Association of CPAs members are saying about private equity and succession planning
19:25 – The top-level conversation: are we picking the right PE partners?
20:06 – The case for remaining independent and why different firm models are healthy for the profession
20:50 – What non-decision-makers feel about PE: caution, valid concerns, and fear of change
21:17 – Why settling on a PE buyer too soon is one of the biggest risks in a sale process
21:42 – Why every PE firm is different and why comparative analysis matters more than people realize
22:23 – Football story: handing the ball to Troy Smith and getting tackled by Ted Ginn Jr.
25:17 – What the experience after the tackle taught Rebekah about community showing up for people
26:45 – Book recommendation: “The Upside of Stress” by Dr. Kelly McGonigal
TRANSCRIPT
Brannon: I’m Brannon Poe, and this is The Accountant’s Flight Plan podcast, where you can enjoy engaging conversations about mergers and acquisitions and accounting practice management. Listen in on strategies to build a more fun and valuable accounting firm.
Welcome to The Accountant’s Flight Plan podcast. Today I’m talking with Rebekah Brown Olson, CPA. She serves as the CEO of the Maryland Association of CPAs. She has spent over a decade working for the profession there and brings a practical, on-the-ground perspective to the challenges firm leaders are navigating right now. She was named one of Accounting Today’s Top 100 Most Influential People in Accounting in 2022 and is known for connecting big-picture trends to real-world implications, helping firms think differently about leadership, workforce development, and what it means to build a future-ready profession. Rebekah, thanks for being here.
Rebekah: Thank you for having me. Really glad to be here.
Brannon: What brought you to the Maryland Association of CPAs?
Rebekah: How much time do you have? I entered the CPA profession through a traditional route: university, majored in accounting. There’s a little nuance there. Because of the 150-credit hour requirement at the time, I double majored in accounting and sports management. I went into a firm, got my CPA within three years, got promoted, and then had what I’d call a quarter-life crisis about the work I was doing. A bit of that burnout that can happen in any profession.
The moment of clarity actually came through a leadership assessment we were doing during a training session for seniors. My leadership style came back as considerate and spirited. I thought those were great words. But when I looked around the table, everyone else had been categorized as direct and systematic, and I thought, maybe there’s something to this. I started exploring what that might mean for my career. I had some natural gifts and strengths I wasn’t able to use the way I wanted in that firm environment, so I started figuring out what might fulfill me more.
I landed in a part-time role with the Maryland Association of CPAs, developing curriculum for firms. What I had always loved in the firm was training interns and first-year hires. That was 13 years ago, when I was just trying to figure out what I wanted to do next. I had my CPA. I knew I wanted to do something connected to the profession, just not in the same way. That part-time work developed into full-time. I ran the membership team, then took on the foundation for a while, and then three years ago the board asked me to become CEO. It’s a career path I would never have imagined for myself, but I love it.
Brannon: I can relate to some of that. I started at Ernst and Young and burned out pretty fast. I was a little different, a little out of place, and felt it. So it’s great that your leadership strengths have been rewarded.
Rebekah: I love getting to say I work for the CPA profession. I don’t work in it anymore in the technical sense, but I get to talk to really smart, wonderful people in the profession every day. I get to advocate for it, think about how we get more people into it, what we do to retain them, all of those things.
Brannon: What are you seeing in the big picture right now?
Rebekah: It’s an interesting question because everything is changing so fast, and I think that is the observation itself. We need to get good at change. That’s true for society broadly, but even more so for our profession right now. I don’t have a perfect five or ten year answer, but what draws me to this work is the role that community plays in navigating rapid change and increasing complexity. You cannot physically or mentally know everything. But you can know a lot of people. My job is really to connect people to each other within the profession. As I look out five to ten years, being part of a community in the profession more broadly is the difference maker in the success of firms, careers, and organizations. If we try to figure everything out on our own, or just ask ChatGPT and see what it says, we’re missing the broader picture.
Brannon: I completely agree. The amount of change is hard to deal with, and I think it’s going to continue to accelerate. What are you seeing around recruiting students into the profession?
Rebekah: The pipeline has been the alarm for several years, and the work done to raise that alarm is starting to produce results. Economic instability also helps, because accounting is a very secure major and career generally. I was at the University of Maryland’s accounting graduation dinner just a few weeks ago and was genuinely encouraged, both by the number of students and by the students themselves. I found myself connecting a few of them into other meetings immediately because they were already remarkable leaders, coming from different backgrounds and second-career paths. That’s exciting.
Brannon: What about people leaving the profession? When I started in the early 90s, it was not uncommon for firms to hire three people planning for one or two to leave. That turnover was built into the recruiting model. Are you seeing better retention?
Rebekah: I think of the profession more broadly, not just firms. We’re doing a better job than we were in the Covid era of maintaining people in the profession overall. The move from public to private still happens. Moving from one public firm to another still happens. I think it is happening a bit less, but I’m not certain how much of that is intentional versus just the economy and environment around us. It’s hard to isolate the contributing factors.
Brannon: I have a theory that private equity investment is going to drive salaries up in this profession, and I think that will also drive more poaching. Do you have thoughts on that?
Rebekah: I used to hear that word more before the pandemic and less recently. There has been a bit more of a collaborative feel lately, less of a protecting-your-people sense. I hope that trend holds. I do hope salaries go up, because the research is clear that starting salaries were too low, and that has been a barrier to attracting people into the profession. That has improved somewhat, but probably not to the degree it needs to. I can see your theory playing out, even if I haven’t seen it materialize fully yet.
I also think that with private equity comes change, and there are people who will resist that. What I expect to see is something of a barbell-shaped profession, at least for a period. We will have very large firms because of PE consolidation and mergers, and we will have very small firms because there will be CPAs who leave the newly acquired environments and say, this isn’t for me, and they will go build something entrepreneurial and independent. The midsize firms will have been absorbed into the large ones before the new small firms have had time to grow up. So we’ll have this period where the middle is largely gone.
Brannon: How do you think that affects small firms specifically?
Rebekah: Specialization is certainly one of the answers. And technology creates real opportunity there too. Large firms have big budgets for major implementations, but smaller firms can move faster. They can adopt and adapt more quickly, they can specialize faster. There will still be a home for every type of client. The environments will just look very different from each other.
Brannon: If you were advising a firm owner who is 5 to 10 years from an exit, what would you encourage them to focus on?
Rebekah: Two things. First, get good at change. A 5 to 10 year plan cannot be created and then sit on a shelf. It has to be constantly refined by new information and circumstances, monthly, quarterly, certainly annually. Strategy has to become a habit. Second, involve your people. If you’re in that leadership role and looking toward retirement, you probably have someone in mind for the next chapter. Make sure they know that, and involve them in building what comes next.
One thing I saw repeatedly when I worked with firms through our Business Learning Institute, which did strategic planning work globally before we transferred that entity to the AICPA, is that the firms that got real alignment were the ones that brought their teams into the strategy conversation, even briefly. It doesn’t have to be every person in a large firm. But there is an element of letting people weigh in, even just asking what they think is missing or where they see themselves fitting in. As the quote goes, in order to buy in, people have to weigh in. Sometimes the best insight came from the firm administrator who interacted with clients the most because she was the one doing the scheduling. You don’t always know where the sharpest perspective is going to come from.
Brannon: The secondary benefit of that is vision casting. Everyone in the firm knows where you are headed. I think so many businesses, not just accounting firms, underinvest in that. When you give people the vision, they feel more secure. And I think it is a significant retention benefit.
Rebekah: Absolutely. And if someone is not engaged or bought in after that process, that’s okay too. Not every culture is right for every person, and knowing that early is better for everyone.
Brannon: What are you hearing from your members about private equity and how it is shaping their succession planning?
Rebekah: I think it’s somewhere in the middle, and it varies widely. The conversation at the decision-making level tends to be around: if we go this route, are we choosing the right partners? That question of partner selection is a big one. There are also members who are adamant about staying independent, and I think that’s great too. We have always had one dominant model for how a CPA firm operates, and this moment is actually an opportunity for the profession to have multiple models. Some PE arrangements will be a great fit. Others won’t. You need to have the right client base, the right culture, the right team for any of it to make sense.
For the people in those firms who aren’t making the decision, the reaction is more cautious. Some of that is fair concern based on what PE can look like in other industries, and some of it is just the discomfort of change. It’s hard to generalize because there are genuine exceptions in both directions.
Brannon: What we see in M&A is that the biggest risk for people thinking about selling or taking PE money is that they settle on a buyer or investor too soon. They don’t weigh their options carefully or do enough comparative analysis. PE firms are very different from each other in terms of culture, how they integrate firms, and what they expect. It’s actually more important to understand your PE buyer than it has ever been in a traditional sale. You are not just selling and walking away. You are tied to that partner.
Rebekah: Exactly. Your firm’s legacy can shift. The concerns that team members have can be valid. That’s why choosing carefully matters so much.
Brannon: Do you have a memorable story to share?
Rebekah: This one is career-adjacent. I mentioned I double majored in accounting and sports management. I went to Ohio State specifically because I wanted to work in sports, in the finance and accounting side of the NFL in particular. It wasn’t until I took an accounting class there that I thought, this is going to be useful for understanding the business side, and also, I’m actually pretty good at it.
The fun part is that I wanted to work with the football team. Ohio State’s football program is well known. I got the opportunity to try out as a field manager, which meant I went to a practice in Ohio Stadium during a live scrimmage. They put me in the middle of the drills. My job was to hand the ball to the quarterback, who would throw to a wide receiver, who would catch it and throw it back to me so we could reset. At the time, the quarterback I was handing the ball to was Troy Smith, who went on to win the Heisman Trophy. Very cool as a football fan to be in the middle of that.
Later in the scrimmage, they had me run the chains on the sideline. Nobody told me the first rule of working the chains, which is to drop the chains and get out of the way when the play is coming toward you. I learned that the hard way. Ted Ginn Jr., who went on to play in the NFL, caught a pass and ran directly into me. I got a cut on my chin and a black eye. That was the end of my career as a field manager at Ohio State. I had the accounting degree to fall back on.
What I also remember is what happened after that, because someone else got hurt more seriously later in that scrimmage. And I got to be part of what it looks like when a community comes around someone who is hurt. I’m a person of faith, and my faith is really important to me. I got to kneel on the field of Ohio Stadium and hold hands with the Ohio State football team and pray for that individual. As a freshman at Ohio State, that was a significant moment. It was a reminder of what community looks like when it shows up for people. The same thing I saw in that CPA session that changed my career direction. It keeps coming back to that.
Brannon: That’s a great story. I think accountants always have interesting things to share.
Rebekah: One accountant at a time, we can prove that.
Brannon: Last question. Do you have a book recommendation for our audience?
Rebekah: I was trying to narrow it down to just one. For firm leaders in particular, I’ll go with “The Upside of Stress” by Dr. Kelly McGonigal. There is also a TED Talk if you prefer that format. I actually watched the TED Talk first and then read the full book. What it did for me was change the way I think about how my body responds to stress, and how to use that response as an advantage rather than something to be managed or avoided. Stress comes with the territory of leadership. You are responsible for the success of organizations and people, and that is genuinely hard. If we learn how to make stress work for us rather than against us, I think we will all be better off.
Brannon: We will put that in the show notes. Rebekah, thank you so much for joining us. I’ve really enjoyed this conversation.
Rebekah: It was wonderful. Thank you so much.
