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.
If you talk to most firm leaders right now, there’s a similar pattern that comes up. Pipeline feels less consistent. You’re not getting pulled into as many opportunities. Deals that do come in take longer to close. You’re doing the right things, in many cases more of them, but it’s not translating the way it used to. What makes it frustrating is that nothing is obviously broken. Your work is strong. Your clients get results. Your team knows what they’re doing. And yet, something feels off.
If you’re a business owner looking at AI, you’ve probably felt the same tension we did: AI is moving fast, clients are asking for it, and it’s hard to justify building everything in-house from scratch. So we partnered with an outside AI firm to bring an AI capability to market quickly — and learned a painful lesson when that firm abruptly shut down with no warning. Here’s what happened, what we were building, and the safeguards we’ll never skip again.
Every year, Stanford’s Institute for Human-Centered AI publishes the most comprehensive independent assessment of where artificial intelligence actually stands. The 2026 edition runs 423 pages across nine chapters. I read it so you don’t have to.
If you’re running a boutique professional services firm, you’ve probably embraced Greg’s hyper-specialization thesis of winning by going narrow and deep in your market. Pick your niche. Own it. Become the obvious choice.
