For many founders and owners of professional services firms, the hardest strategic question isn’t how to grow—it’s how to transition without undoing what took decades to build.What happens to the company when you step back? What happens to the people who helped build it? And what happens to the culture, independence, and values you care deeply about?
There’s a list of roles in every boutique firm that exist on paper but rarely get done well. Account management. Service design. Marketing. Sales management. Every founder has the list.
It wasn’t because founders didn’t care. It was because the math never worked. And the math just changed.
Two years into the AI era, many boutique professional services founders I talk to are stuck. The initiative isn’t dead, but it isn’t really moving either. There’s activity. Meetings, demos, vendor calls, but very little has actually shipped. No new economics on the P&L. No real change in how the firm operates. No buyer would look at the business and call it AI-native.
Like many Founders, I’ve spent hundreds of hours researching, using, testing, and talking to my peers about AI the last 12-18 months.
In those hundreds of hours, I’ve come to notice one fork in the road that’s quickly become critical in whether AI is creating value or destroying it: AI is either being used to cut costs, or it’s being used to compound expertise.
For founders of growing firms, retreats like these may feel familiar. For most COOs and certainly for me, they do not. I have an unusual seat at your table and sit in your conversations as a bit of an outsider.
After three retreats, I have something to tell you.
I have attended three Collective 54 retreats in the last 7 months. I am not a founder – I am the COO of a boutique professional services firm.
For founders of growing firms, retreats like these may feel familiar. For most COOs and certainly for me, they do not. I have an unusual seat at your table and sit in your conversations as a bit of an outsider.
After three retreats, I have something to tell you.
My partners and I have built Rootstrap over fifteen years. In that time, the firm has passed through many distinct inflection points.
These are the moments when what has been working stops working — sometimes loudly, more often quietly. Revenue plateaus. The leadership team that ran a $5M firm breaks under a $10M load. The meeting cadence designed for thirty employees suffocates a team of a hundred.
Information-overload. Conflicting advice. Market disruption. Margin pressure. The once in a lifetime opportunity enabled by AI. Change at the speed of… well…AI.
How do we, as leaders, make sense of it all? How can we embrace this unique time in which we live and work to capture the value of this fleeting moment? How do we avoid burning out in the process?
Over the past 30+ years, my firm has built a business focused on evaluating the digital customer experience delivered by the nation’s leading financial services and healthcare companies. We track how these institutions onboard new customers, deliver information, handle service requests, and compete on experience – not just products or price.
Launching a new product isn’t just about having something innovative—it’s about making sure people notice, understand, and ultimately care. In a crowded marketplace where attention is scarce and skepticism is high, success depends less on what you launch and more on how you present it.
For twenty-five years, I have lived by a simple truth. The service business is a human endeavor.
At OneAccord, we lead middle-market companies through transition. We do not do this with slogans. We do it by placing seasoned operators directly into leadership roles. These are men and women who have sat in the seat themselves. Because of this human-first heart, I was a skeptic of Artificial Intelligence.
