New Deal Partner: Rob O’Brien of ChangePilot
Helping More Founders Exit with Confidence
Breakwater M&A is proud to announce Rob O’Brien, founder of ChangePilot, as our newest Deal Partner.
Rob brings years of experience building, selling, and advising small-to-mid-market businesses. His founder-first perspective perfectly aligns with Breakwater’s mission—to help entrepreneurs achieve life-changing exits with clarity, confidence, and maximum value.
“I realized I had skills that could really help business owners achieve their goals of exiting successfully—and it felt good to help them do it.” — Rob O’Brien
From Founder to Advisor: Rob’s Story
Rob O’Brien’s M&A journey began like many great stories—with firsthand experience. After building and selling two of his own companies, Rob realized he loved the process of helping others do the same.
When a business owner once reached out asking for help selling her PR firm, Rob stepped in to assist for free. That experience ignited a passion that became ChangePilot, his boutique M&A advisory firm dedicated to helping owners prepare for and execute successful exits.
Rob’s mission is simple:
“If a business owner puts their trust in me, I owe them the right advice—not just the advice that gets a deal done.”
Why Owners Choose Rob and ChangePilot
Rob primarily works with founders planning to sell within three to five years, often those preparing for retirement or their next chapter. His approach combines practical, empathetic guidance with tactical readiness steps that increase valuation well before going to market.
Here are some of the core strategies he helps owners implement:
Delegate leadership early: Install general managers and empower decision-making to reduce owner dependence.
Secure client contracts: Convert handshake deals into written agreements to stabilize post-sale revenue.
Clean financials: Ensure accurate, organized accounting and reporting before diligence begins.
Document systems: Create an “instruction manual” so the business can operate smoothly without the founder.
“Buyers will pay more when they see a business that runs without the owner. My advice: work yourself out of a job.”
— Rob O’Brien
Preparing for Exit the Right Way
For business owners looking to sell within the next 12–24 months, Rob emphasizes one thing above all: assemble your deal team early.
“You’ll need a broker, an M&A accountant, and a lawyer,” Rob advises. “The earlier you get those people involved, the smoother your deal will go.”
He views the broker as the “coach” of that deal team—keeping everyone aligned and ensuring the process stays on track through valuation, negotiation, and closing.
Why Rob Joined Breakwater M&A
When asked why he partnered with Breakwater, Rob pointed to a shared vision: leveraging technology, systems, and specialized roles to help more deals reach the finish line.
“Breakwater is building a platform that helps more deals get done. By systematizing the process, I can spend more time with clients and less time buried in data rooms and admin work.”
Breakwater’s platform empowers experienced advisors like Rob to focus on what truly matters—guiding owners through high-value decisions—while the firm handles infrastructure, data, and buyer network support.
As Breakwater founder Morgan Tate shared:
“Rob fits perfectly with our values—attention to detail, client-first focus, and genuine care for founders. We’re thrilled to scale alongside him.”
What Owners Can Expect Working with Rob
Rob focuses on quality over quantity—limiting the number of clients he takes on so each owner receives his full attention.
“When someone trusts me to sell their business, that’s an honor I take seriously. I only take deals I can manage personally from start to finish.” — Rob O’Brien
If you’re an owner with $1M–$50M in revenue considering an exit in the next few years, Rob can help you see your business from the buyer’s perspective—so you can make smart, strategic decisions now that pay off later.
Ready to Start Planning Your Exit?
Whether you’re six months or three years away from selling, the right preparation makes all the difference.
👉 Book a confidential exit-readiness call with Breakwater and Rob O’Brien here.
Full Interview Transcript
(Included below for transparency, education, and SEO purposes.)
Morgan Tate – Breakwater M&A (00:00)
Rob, you could start with giving us your quick origin story and what led you to start ChangePilot.
Rob O’Brien (00:07)
Sure, Morgan, thanks for having me on. I started and grew and sold two of my own businesses. And then I was looking to buy a third and I was having trouble sourcing deals. So I was speaking to brokers and I wasn't getting anywhere. Eventually I made a post on LinkedIn saying, does anyone know anyone that's looking to sell a business?
Somebody reached out—they asked me if I wanted to buy their PR business. I wasn’t a PR person, so it didn’t really interest me, but I could tell that this person needed some help because they didn’t really know where to start. So I offered to help them sell it for free. It turned into a great experience for her—she got more than she expected, a big contract with the company that acquired her, and she was thrilled.
That experience made me realize I had skills that could be used in this field—and that helping founders exit made me feel good. It felt meaningful to help her achieve her goal of exiting her company and building a nest egg for retirement. So I decided to jump in.
Morgan Tate (01:13)
Amazing. You’ve now worked with a variety of different founders and operators. Could you dive into that core mission?
Rob O’Brien (01:30)
I find that when someone puts their trust in me to sell their business, I have a responsibility to give them the right advice—not just to go through the motions. Sometimes that means telling people it’s not the right time to sell. I might tell them to fix certain things or make improvements before going to market.
If they’re trusting me, I owe them honest guidance—not just what’s in my best interest to get a deal done.
Morgan Tate (02:15)
Then can you describe your typical clients?
Rob O’Brien (02:23)
Sure. Anyone thinking about selling in the next three to five years—often founders approaching retirement who want to unlock the value in their business. If you’ve got revenues between $1M and $50M, you probably have something buyers want. It’s smart to start early and talk to advisors now so you know what your future will look like.
Morgan Tate (03:00)
What’s the biggest mistake founders make when preparing to sell?
Rob O’Brien (03:06)
Too many don’t put general managers in place. It’s critical to push decision-making down into the organization. It makes the business less stressful to run and more valuable to buyers. Build a company that runs without you—that opens doors to more buyers and higher valuations.
My top advice: work yourself out of a job and become the owner overseeing the business, not the manager running it.
Morgan Tate (03:50)
For founders watching this who want to get out of the weeds, our Exit Navigator program is designed to help with exactly that. Maybe you can share a few other overlooked ways businesses can increase their valuation?
Rob O’Brien (04:14)
One of the big ones is customer contracts. Buyers love seeing long-term contracts because it shows revenue security. Owners often hate asking clients to sign deals, but doing so drives up value.
Another big one is clean financials. I’ve seen deals fall apart because reporting wasn’t where it should be. Work with your accountant—it will pay for itself.
And finally, document your processes. When buyers see written processes, they feel secure that operations can continue without you. It’s like giving them an instruction manual for running the business.
Morgan Tate (05:42)
Great advice. If a founder plans to sell in 12–24 months, what are the two or three most important things they should do right now?
Rob O’Brien (06:03)
First, start assembling your deal team—get your broker, M&A accountant, and lawyer in place early. Those advisors will pay for themselves. You might also need bankers or wealth advisors, but your broker acts as the coach of the team, managing everyone and keeping things moving.
Morgan Tate (06:44)
Amazing. Let’s talk about your partnership with Breakwater—what made you want to join the network?
Rob O’Brien (07:03)
Breakwater is building a platform that helps more deals get across the finish line. By bringing in specialization and systems, I can focus on clients and buyers instead of admin work or managing the data room. I’m excited to see the partnership grow as Breakwater continues to build tools that make deals smoother and faster.
Morgan Tate (07:43)
We’re thrilled to have you on board. Rob really fits our values—client care, attention to detail, and helping founders make smart exits. This partnership lets him spend more time on high-value client work instead of getting bogged down in admin.
Rob O’Brien (08:41)
Owners wanting to exit now or within three years should start the conversation early. Talking with advisors helps you see your business from a buyer’s perspective—and that can change how you operate leading up to a sale.
I focus on successful outcomes for my clients, which means I only take on deals I can personally manage. Selling a business is a huge act of trust, and I take that responsibility seriously.
Morgan Tate (10:06)
Thanks Rob—we’re really excited to work with you.
Rob O’Brien (10:13)
Thanks for having me, Morgan. I’m excited for the future—great things ahead.
Final Thoughts
Rob O’Brien embodies what Breakwater looks for in a partner—experience, empathy, and excellence. His addition to the Breakwater network strengthens our mission to help more founders navigate successful exits with confidence.
If you’re thinking about selling your business within the next few years, connect with Rob O’Brien and the Breakwater team to start mapping your strategy today.
👉 Book your confidential discovery call here