Ryan Ross is not a CPA, and he does not plan to become one. In 2025, he bought Quality Back Office through Poe Group Advisors, combined it with his own firm, and found that the software he needed didn’t exist, so he built it. In this episode of The Accountant’s Flight Plan, Brannon Poe and Ryan explore how an entrepreneurial buyer scales an accounting firm through acquisition and why honesty with clients anchors a smooth transition.
Ryan is a U.S. Marine Corps veteran who left the service in 2019 and launched a bookkeeping firm for real estate investors and real estate adjacent professionals. After years of steady organic growth, he moved to growth by acquisition in 2025 and now has two more deals in the pipeline. The combined firm operates as QBO, with a management layer that frees Ryan to focus on client service and acquisitions. As he puts it: “You do not need to be a doctor to run a hospital.”
Brannon adds the seller’s perspective. Some sellers hesitate when a buyer is not a CPA, and Ryan’s answer is scale: once a firm has a stable team and backup for key roles, an entrepreneurial owner can lead it well. Brannon also affirms Ryan’s choice to tell clients the truth about the sale. Poe Group Advisors calls the alternative masking, and clients tend to spot it quickly, which leads to eroded trust and added difficulty in maintaining long-term client relationships.
The Conversation Covers:
- Why a non-CPA owner can lead an accounting firm once scale and a management layer are in place
- How the “hit by a bus” test pushed Ryan from organic growth toward acquisition
- Why telling clients the truth about a sale protects the trust at the center of the relationship
- How Marine Corps habits, including asking “why do you do it that way?” shaped the integration of a multi-office firm
- How a QuickBooks lockout and a price increase led Ryan to build Woven, an all-in-one platform with optional AI
- Why Ryan believes AI will free accountants to spend more time with clients, not less
Ryan’s view of the road ahead is practical: AI can supplement the advice, but it cannot care about a client’s family. Firms that use technology to make room for real conversations will stand out.
This Episode Is For…
This episode is for accounting firm owners curious about how a non-CPA buyer approaches an acquisition, sellers wondering how to talk with clients and staff about a transition, practitioners ready to look at where their software stack creates friction, and leaders interested in using AI to support the team without losing the personal touch.
Questions:
Can a non-CPA successfully run an accounting firm? Ryan Ross, founder of Quality Back Office and creator of Woven, says yes once a firm has scale and a management layer in place. He invested time and money in hiring a strong tax manager and bookkeeping manager, and he relies on his industry knowledge of what clients need. Brannon Poe adds that a stable team with backup for key roles reduces a firm’s dependence on any one owner’s technical expertise.
Should a seller tell clients about the sale of their accounting firm? Brannon Poe, founder of Poe Group Advisors, advises sellers to be honest about the transaction rather than masking an exit as a merger. Clients tend to notice when the story does not hold together, and even a small white lie can weaken the trust at the center of the accountant-client relationship.
How can a buyer integrate an acquired CPA firm without losing clients or staff? Ryan recommends keeping service and personnel consistent for clients, being candid about the change, and spending extra time with clients tied to the seller. Having the former owner stay on as an advisor and placing a partner locally to greet clients from day one also helps. He approaches integration by asking: “Why do you do it this way?” while respecting what the seller built.
How is AI changing accounting software and the role of the accountant? Ryan built Woven so that AI can be turned off completely, builds a private internal record of each client, and routes its work to a person for review. He believes AI should free accountants to spend more time with clients. Brannon predicts that firms without advisory-level services will see business clients leave.
TIMESTAMPS
00:00 – Welcome and guest introduction: Ryan Ross, Quality Back Office and Woven
01:53 – Why Ryan moved from organic growth to growth by acquisition
05:10 – Can a non-CPA run an accounting firm? Scale, management layers, and the “hit by a bus” test
08:47 – Keeping clients through a CPA firm acquisition: why honesty beats masking the truth
12:55 – How Marine Corps habits shaped the integration of an acquired accounting firm
15:40 – “Why does it hurt?” The question behind every process improvement
18:01 – The QuickBooks lockout and payroll pain that led to Woven
22:12 – One screen, one login: how Woven brings the ledger, clients, and tasks together
23:52 – How Woven’s AI works: optional, human-reviewed, and private
26:09 – What Ryan is doing differently on the next two acquisitions
27:44 – Why the personal touch matters more in the age of AI
29:34 – Ryan’s Marine Corps story: leading with humor and humility
31:59 – Book recommendation: “Business by the Book” by Larry Burkett
BOOK RECOMMENDATION
Business by the Book by Larry Burkett
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.
All right, welcome to The Accountant’s Flight Plan podcast. Today I’m talking with Ryan Ross, founder of Quality Back Office, a multi-state accounting and bookkeeping firm serving real estate investors and real estate adjacent professionals.
Ryan left the U.S. Marine Corps in 2019 and launched the business as [TRG Bookkeeping, name to confirm], growing it through a hands-on, advisory-first approach that treats bookkeeping as the bridge between financial performance and business results. In 2025, he made the shift from organic growth to growth by acquisition, and that’s where we came in. You purchased Quality Back Office through Poe Group Advisors, and you’ve rebranded and combined the firm under the QBO name. You now have two more acquisitions in the pipeline.
That first deal took you somewhere you didn’t expect. While integrating the acquisition, it became clear that the software the firm needed didn’t exist, so Ryan built it. That platform, called Woven, consolidates general ledger, bank feeds, reconciliation, invoices, month-end close, a client portal, and tax work into one system with AI built throughout.
Ryan, welcome to the show.
Ryan: Thanks for having me. I really appreciate it.
Brannon: That’s a great story. Let’s dig into it. First, walk us through when you decided to switch from organic growth to going for an acquisition. What made you ready to take on that endeavor?
Ryan: One of the biggest things was that organic growth was great. It sustained us and allowed us to get our feet set and understand what clients really wanted and needed, and what they didn’t like, which was part of the journey. Then it became evident that you can pursue organic growth, which is slow and steady and great, or you can grow by acquiring a firm.
Part of my story goes back to when I was trying to get out of the Marine Corps. I’m Christian, and I prayed a lot. I was asking God what paths he was putting me on, because it definitely felt like the Marine Corps wasn’t it anymore. He laid it on my heart, and I didn’t know why at the time, but he said, let’s go into accounting. So we started there. I always joke that the plan he put on my heart was significantly more thought out and greater in scale than the plan to get there.
Over time, I kept going down the path of thinking it was time to buy something. We ended up buying a different business as well. We owned a towing company, and we really liked the acquisition side of it. There are a lot of things about it we liked. We just kept praying, and we found another business, which we call Quality Back Office. One thing I pray all the time is, God, if this isn’t it, close the door, and close it hard so it’s obvious. It never seemed to do that, so we just kept going, step after step.
What it has given us is a lot of capabilities we didn’t have before. I’m not a CPA, and I’ll never be a CPA. Those of you who are, you’re doing God’s work. I personally didn’t have much interest in learning to prepare the taxes, but I had a really good understanding of them, and I wanted to supercharge our ability to offer that to our clients. My client base is largely real estate, so it made sense to find a firm with a similar client base, take those strategies and add them to our clients, and cross-sell. So far it has come with good success, even just in taking the current client base and maximizing what we get out of it. It supercharges us to go from organic to acquisition. We’re still doing organic, but the intent is to make the multiple considerably larger by the end of it.
Brannon: What’s interesting about your story is that we sell a lot of CPA firms, and sometimes when we send buyers to our clients, if the buyer isn’t a CPA, some sellers reject them. It’s hard to understand how a non-CPA could run a CPA practice. I think part of the answer is scale. If it’s scaled as a business, it’s totally operable by an entrepreneurial owner. Once a business reaches a point where the team is relatively stable, that expertise isn’t really needed from the owner, and if you lose a key person, you have redundancy in those roles and it doesn’t cripple you. I get why an acquisition makes sense: it gives you scale, and the more scale you have, the more stability you have in your team. Any thoughts on that?
Ryan: One thing I learned is that I’m going to die eventually. That sounds morbid, but I’ve always planned around the “hit by a bus” theory. If I get hit by a bus and I’m the only one running the company, that doesn’t do my family any favors, and it doesn’t do my clients any favors. One added benefit of buying is that we now have a management layer. There are our bookkeepers, our CPAs, our admin staff, and now managers in between us and them. The quantity of problems that reach us is smaller, but they’re harder, and we can focus our time on acquisitions and client service.
I’d also argue that you don’t need to be a doctor to run a hospital. The ability to run a business matters, and it matters that you know the industry. I think this would be really hard to do if I didn’t know anything about accounting, didn’t understand clients, and didn’t understand what hurts for them. We hired a tax manager, and we spent a lot of money and a lot of time finding that person so we knew our clients would get good advice. I could give him a scenario and tell that the advice he’d give was sound and client first. Our bookkeeping manager was the same. The idea was that good management in place lets you scale to another level. And even if we buy one of the two firms this year, folding all of that into one is where the magic happens.
Brannon: Right, you don’t need to be a doctor to run a hospital.
Ryan: Exactly. And the gentleman we bought Quality Back Office from had a daughter who worked in the company. She looked at me and said, we really thought you guys were like PE, because there were three partners and you had everything covered. I said, I guess you could say that, but we’re not a PE firm being a bunch of jerks. That helped ease their fears. We’re not here to strip the company and let everybody go, and we’re not going to jack up client fees or anything like that. That was never our intent.
Brannon: I’m sure you learned a lot on that first acquisition about the handoff. What did you learn about holding on to clients and staff through that transition?
Ryan: We learned lessons on both sides of the coin. What went well was that clients wanted to hear that the firm had been sold. They wanted to know who bought the firm, but their biggest concern was, am I still going to get taken care of? There were enough people in that firm that the owner didn’t touch every client, and those clients were easier to keep because they didn’t care so much as long as nothing changed: their person didn’t change, the service didn’t change, and they still came first. But they wanted to know the firm had been sold, because one piece of advice we heard was, you don’t need to tell anybody, just keep it the way it is. I didn’t feel comfortable with that.
On the flip side, some clients were still tied to the owner, and those were more challenging. They’d say, he’s leaving, so why should I stay? We told them, he’s leaving, but not really, because he’s still around as an advisor, and we’re going to take a lot of time to get to know you and show you that we’re not just the village idiots trying to run a firm we know nothing about.
At the end of the day, honesty mattered a lot. One of the first things I tell somebody is, the day I’ve got it all figured out and I’m perfect, you’ll be my first phone call, but don’t expect it. We’re going to mess things up. We had an issue, which we’ll talk about later, where QuickBooks locked our entire account and my entire firm was locked out. I had to call a bigger client whose accounts payable we handle, and I said, this is where we’re at, I’m really sorry this is affecting you, we’re still trying to figure out why they did this, and if we messed up along the way I’ll let you know, but here’s the story. I think he really appreciated the candor. Ultimately it wasn’t us, it was QuickBooks.
That honesty matters because clients let you see their financials and everything about their life like nobody else can, and they don’t want someone in there they don’t trust. Gaining that trust, especially with the clients tied to the seller, was one of the challenges for sure.
Brannon: You bring up a really good point, because we advise our clients to do just what you did, which is to be honest about what’s happening with the transaction. If it truly is a merger, we’ll be honest about that. But most of the time, when the seller is accomplishing an exit, you need to be honest with clients about that. The advice you heard, we call it masking: we’ll mask this as a merger and nothing has changed. What we’ve experienced is that clients are very smart and figure out quickly when what you told them isn’t true. Even a little white lie, they’re going to remember it, and it erodes the trust of the relationship, which is the key component of an accountant-client relationship.
Ryan: Absolutely, and they can spot it a mile away. I didn’t want any opportunity for ambiguity or the appearance of impropriety, so we tried to be as candid as we could. That doesn’t mean we got it perfect across the board, but we made that attempt, and I think it has panned out pretty well.
Brannon: Let’s talk a little about your Marine Corps background. We have one of our top advisors who is a former soldier, and he talks about the systems he learned in the military, built on precision, accountability, and systems. How did some of that show up in how you approached the acquisition?
Ryan: One of the things was understanding how the company was operating. We really liked the company, but we realized it didn’t operate with maximum efficiency, which I don’t think surprises most people. It had five physical offices throughout the country, so there were costs associated with that, and people were spread out. We learned later that some people had never even met others in the company. We loved the business, but there was a lot of room to make things smoother.
What I took from the Marine Corps is the question I always asked when I went to a new work center. I loaded bombs on planes, which doesn’t translate to anything in the real world, but my job was quality assurance and safety observer. I watched people work, and I always asked, why are you doing it that way? Maybe it wasn’t efficient, or it wasn’t by the publication. Almost all the time the answer was, that’s how we’ve always done it, and if I’ve ever heard a bad answer, it’s that one. We get into a routine, and it’s less inconvenient because that’s how we learned it.
That’s how we approached the business we bought: why do you do things this way? It wasn’t about tearing it down. They had built a great business, and we had built a really strong business. The question was, why are we doing it this way when this other option exists? The task management software we moved to, he had never heard of, so I can’t fault him for not moving to it. He knew what he knew, and he did a great job. But it didn’t allow for maximum communication and efficiency of information throughout the firm, and we saw that as a good opportunity.
In my head, it’s ingrained: how do we take any task, small or big, break it up, and make it efficient and easier? I always ask, why does it hurt to do this thing? Why do I dread this task? Once I start asking that question, I drill into it and figure out why it hurts.
Brannon: Great question. Why do I hate doing this? It’s worth fixing.
Ryan: And as we get further into the conversation, that’s the premise of why I built the software. I asked the seller, why does it feel like this hurts? He’d tell me about a frustration, and I’d try to understand why. I’d also ask myself whether I’m so smart and insightful that I have an answer he didn’t think about. So I bounced things off him, and he was great at collaborating. He’d say, I’ve tried that. The ability to collaborate came from the Marine Corps too, because there you don’t have a choice. My desire to be efficient and my willingness to say I don’t know everything and ask questions are elementary skills, but they were honed in the military.
Brannon: It’s great that you had a seller who was open-minded enough to help you think things through. Some sellers get their feelings hurt when someone wants to change what they built. It’s good that he let go enough to let you do what you wanted to do.
Ryan: I think it helped that he opened that door at the beginning. He said, we use this, but I don’t know that it’s what you guys should be using, so feel free to come in, ask questions, and see if there’s something better we could do. I’m incredibly grateful we had that ability with him.
Brannon: Let’s talk about the software platform, Woven, which I love the name of. When you’ve got something that integrates things together, Woven is a wonderful name for it. When was that moment of pain, when you realized what’s available in the marketplace is lacking and we can do better?
Ryan: The first moment of pain was earlier this year, when QuickBooks locked us out and it took two and a half weeks to get our account back. I think they were holding about $100,000. It stemmed from information they said they didn’t have on our company, though we had gone through their certification process a couple of times because of the switch. I thought, why am I beholden to this? But I didn’t do anything with it because I didn’t know what I’d want to do differently.
The next process that hurt so much was payroll. On top of real estate, another subset of our clients is Hispanic and Mexican restaurants throughout the Midwest. I really like them. They’re great people, and I’ve enjoyed getting to know them. A lot of them still like paper and pen. We use ADP for payroll, and some of them mail papers with hours on them. If we’re lucky, it takes 20 to 30 minutes per payroll to check everything: is the handwriting legible, do the numbers make sense. We have a whole spreadsheet that walks through every check, and all I could think was, why does this process stink so much? It’s hard to ask them to change abruptly, so I asked, why does this hurt?
Before January of this year, I was not an AI person. I wasn’t a fan. I just didn’t understand it, and I didn’t care to know more than ChatGPT. Then I started asking people I knew and ChatGPT, how do I fix this payroll process? What started as a way to get the payroll in from the client, by email or text, into our spreadsheet, have it do its check, and spit out exactly what our team member had to review before putting it in ADP turned into this whole process of, everything hurts, QuickBooks and everything else.
The final straw was when I was on vacation at the beach and got another infamous email from QuickBooks saying they were raising prices. The QBO Plus plan was $35 when I started in 2019 as an accountant, and it’s up to, I think, $225 now. Nothing has changed that I use or need. I took all of that, got fed up, and said I’m going to do it all and make it all.
The other problem is that a lot of these platforms are great, but now they’re slapping AI on top and saying, look, we’re AI-driven, and here’s a price increase to go with it. Whether you want the AI or not, you’re tied to it. What hurt for me was being in QuickBooks here, ADP here, a property management software here, and receipt capture up here. I have six screens at my desk for a reason, because there was a time I needed all six. All I could think was, why does this whole process hurt? It should all be in one screen, one login, one place.
That’s where I started. Your ledger, client communication, task management, files, and receipts should all be in one place, so I can see everything about my firm: my billing, my client data, my profitability by client, and I can drill down as far as I want. I want to know how long my employees were in the software and what workflow they were working on, so I don’t have to rely on them to hit the timer. I’m not there to criticize every minute of their day, but I want to know if a client is taking more of our time than they should, and why. So I built it around that. It’s our everything now. The last piece being built is the ability to e-file through the software.
Among all my software, I probably pay about $200,000 a year. Some people might think that’s not a lot, but there will never be a day in my life that $200,000 a year isn’t a lot of money. If I have to go into Drake or another tax program, the software is great and does what it’s supposed to do, but it’s probably as old as I am and feels like it, and I have to go to a remote server. All I’m thinking is, why does this hurt so bad?
In the software, you have the ability to turn AI off completely and use it as the exact same software. AI never touches it. If you connect QuickBooks to it, bringing a client over, it reads the entire QuickBooks file and creates its own brain for that client. It’s all held within the system. It doesn’t go out and talk to anyone. It builds an internal brain and helps you categorize. If you send in receipts, it reads them and either suggests or creates entries based on a certainty level, which I built in, so a lot of those tasks are easy.
On the email side, if a client needs a 1099 or a copy of a sales tax filing you’ve already completed, it goes into your file system, pulls it, drafts the email, and notifies you it’s ready for review. You review it and send it off. Everything is intended to have human review. It’s never intended to be done on its own. The whole way through building it, all I could think was, this process hurts, why does it hurt, and what can I do to make my life easier and my people’s lives easier? At the end of the day, I want them to like coming into work and not have to fight software. That was the premise behind it, and even on cleanup it has been immensely helpful already.
Brannon: Wow. What stage is it at? Is it just for your own internal use right now, or are you starting to think about licensing it to other people?
Ryan: I originally built it only for me, and then somebody smarter than me said I should probably look at selling it. It’s in beta right now. I think we have maybe two or three more weeks of beta, and then it launches to anybody who wants it.
Brannon: Interesting. Well, that’s exciting. That’s a typical entrepreneurial play: you find the pain and you create the solution to solve it. I hope it goes well for you, Ryan.
Ryan: I appreciate that. Thank you.
Brannon: Really quick question on the acquisitions. You’ve got two more in the pipeline. How are you approaching these differently based on what you learned from the first one?
Ryan: We are digging even deeper and wider than we did before. That’s not to say we didn’t do a satisfactory job. I thought we did a really nice job. But we realized that if we had kept going a little further than we thought was necessary, we would have found more. The other thing is being out in front of the clients more. We’re bringing on another partner who relocated to one of our offices near one of the places we’re looking to purchase, so he’ll be there to greet clients from day one.
One of the harder things for us is that I live in Pennsylvania, all three partners live in Pennsylvania, and the offices were in Chicago, Denver, and Durham, North Carolina. They were spread out, and even meeting the clients was tough. So we’ll have a partner who’s just there, who can come in and talk to them, get to know who we are and what we’re trying to do, and have that in-person communication. I value that a lot, and I think a lot of people do. We don’t want to lose that as a firm.
Brannon: That’s good. I do think there’s no replacement for it. In the age of AI, I feel the personal touch is going to become even more valued in the marketplace.
Ryan: I don’t see a world where people truly want to talk to AI all the time. I never will. I like people too much. You can get the answer you need and get the work done with AI, but AI doesn’t care about your family. The ability to sit across from a real human being and know that the advice, maybe supplemented by AI 100%, is coming from a place of caring about the client is important. I don’t think we’re in danger of being extinct as a profession. Even with the platform I built that has AI in it, it’s not designed to replace us. It’s designed to make us better and more like real people to our clients, because we have time to talk to them about them.
Brannon: It frees up your time to do more in person. I think it’s going to change the profession, so that if you’re not offering advisory-level services, a lot of your business clients are going to leave. That’s my prediction. Eventually you’re not going to need a number cruncher or a number pusher. You need somebody with real-world insights, who has seen what works and what doesn’t and can look at a number and say, that ain’t right. Not just that the math doesn’t math, but that something is happening, and let’s figure out what it is and dive into the problem.
Ryan: 100%.
Brannon: Love that. We’re at the wrap-up stage, so I have a couple of questions to close out. Do you have a story you can share, either funny or just memorable? It could be a professional failure that turned into a success, or just a memorable moment.
Ryan: Absolutely. It isn’t really about accounting. It goes back to the Marine Corps, but it was a funny moment where I learned a lot about myself and about leading and managing. We were deployed to the Middle East on an airbase, and my whole job was quality assurance and observing for safety. The Marines had done something that annoyed me to no end. We didn’t miss a flight schedule, but they had done something unsafe.
I remember standing in front of them, as serious as I could be. In the Marine Corps, it’s a bit acceptable to yell, you Marines! I was yelling because I was angry, the stakes were high, and I was stressed. By the way, that’s not really the right way to do it, but that’s how it was kind of done. Our job was to load bombs to be dropped in the Middle East, and I said something to the effect of, we’re here to drop bombs on dead people, right? Complete silence.
Even in the most serious moment, when I was the most frustrated, I realized, you’re still human, buddy. You might be mad at them, but you’re still a goofball who says dumb things too. I relaxed and moved on with our day. But “drop bombs on dead people” is all I remember from that day. It reminds me that I’m still imperfect, and God hasn’t given me infallibility.
Brannon: It’s a great story. I’ve never met anyone who was career military who didn’t have some pretty good stories, and some aren’t shareable to a wider audience.
Ryan: That’s a fair way to describe them.
Brannon: All right, last question. Do you have a book recommendation for our listeners?
Ryan: I do. I have it right here. It has shaped how I conduct myself outside of the military, where I stand, how I talk to people, and what I believe. It’s called “Business by the Book” by Larry Burkett. It’s all about how to be a businessperson as a Christian, how the Bible would guide us through scenarios, and what it really means to be a Christian in the business world. I still read my Bible every day, but it’s nice to hear from a very successful businessperson how he applied it to his life. It’s one of my favorite books, and it grounds me.
Brannon: I think that book has been around for a while, hasn’t it?
Ryan: It has. I want to say it’s from the 90s, maybe 1998.
Brannon: Very nice. Thank you for sharing that. One last thing before you go: what’s the best way for people to connect with you online?
Ryan: The easiest way is to find Quality Back Office on LinkedIn, and I’m on there, Ryan Ross. You can also email me at [email address to confirm]. I’d love to talk to anybody who has questions, whether it’s about acquisitions or software or whatever it is. Those are the two biggest ways.
Brannon: Awesome. Ryan, this has been a great conversation. Thank you for joining us on The Accountant’s Flight Plan, and good luck with Woven.
Ryan: Thank you. I really appreciate it. Thanks for your time.
