Over the past two decades, wealth management has seen its share of change — some of it meaningful, and much of it cosmetic.
We’ve witnessed headline-making mergers and acquisitions, like Schwab’s acquisition of TD Ameritrade. We’ve watched broker-dealers merge, split and acquire each other in a dance that often feels more administrative than innovative. Yes, the logos on the buildings have changed. But has the pace of real, ground-level transformation matched the hype?
For many industry veterans, the answer is often no. Change happens — but slowly. And rarely where it counts most.
At the recent Tiburon CEO Summit in Boston, the conversation inevitably turned to artificial intelligence. In a room full of leaders, the big question wasn’t what AI is, but why it matters. And to me, the most exciting part of AI’s impact isn’t that it’s “disruptive.” It’s that it’s finally allowing us to fix something foundational: the feedback loop.
What Is the Feedback Loop?
The feedback loop is the cycle through which we build, test, learn and improve. In our industry, this has historically been a long and frustrating process. You design something. You pitch it. You wait. You wait longer. Maybe it launches a year later. Maybe it doesn’t.
When I led design and marketing at a leading wealthtech, we were heavily dependent on integrations with custodians like Schwab, Fidelity, Pershing — and most significantly, TD Ameritrade. I remember sitting in meetings where TD leaders would share ambitious visions for their Veo platform and its open API strategy. Schwab would share its roadmap. And then … we’d wait.
And when those long-awaited changes did arrive? They often fell short of expectations. Watered down. Poorly documented. Built on top of legacy systems that no one really understood anymore.
Enter AI: The Feedback Loop Multiplier
What’s different now — what’s actually disruptive — is that artificial intelligence is accelerating the feedback loop.
Developers can build faster. Teams can communicate more clearly. Ideas can be tested and improved in days, not years. AI can even identify the dysfunction buried deep within our existing tech stacks, most of which resemble ancient cities layered with centuries of construction.
A lot of our industry’s foundational technology is still dependent on Common Business-Oriented Language, or COBOL — which was developed in 1959. (Yes, 1959.) Originally designed for business computing, COBOL was revolutionary at the time. But today, it’s a fossil. And yet, many major custodians still rely on it. Not because they want to — but because it’s embedded so deeply into the systems that change feels impossible.
Until now.
The Shift We Need
The opportunity in front of us isn’t just about new tools. It’s about building a better system for change itself. It’s about making the feedback loop faster, tighter and more honest.
Because when the loop improves, progress becomes possible.
And we’re already seeing this play out. At Milemarker, we’re helping firms build intelligent systems that respond in real time, allow for faster iteration and give teams the power to adapt. And when we work with smaller alternatives platforms or cutting-edge fintechs, the difference is clear — they’re nimble, responsive and constantly improving.
This starts with asking the following questions:
- How often do you revisit your processes?
- How quickly can you go from idea to implementation?
- When something’s not working, how fast can you pivot?
Clients expect you to continuously improve their lives. Shouldn’t your business operate the same way?
Whether your mission is to be the most impactful financial planning firm in your city or to lead a national advisory movement, you need a feedback loop that keeps pace with your ambition.
Change shouldn’t be measured in five-year roadmaps or retirement cycles. It should be measured in days, weeks and months — because that’s how progress is made.
Jud Mackrill is co-founder and managing partner of Milemarker, which works with advisory firms to establish data management rules and procedures for their tech stack.
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