Introducing Stack Strategy

During that time, I had the opportunity to help an organization grow from approximately $4 billion to more than $16 billion in assets under management. Along the way, we navigated major technology transformations, cybersecurity challenges, regulatory examinations, acquisitions, platform migrations, and the emergence of artificial intelligence.

I learned a lot. Some of it the hard way.

But perhaps the most important lesson was that successful technology leadership has surprisingly little to do with the technology itself.

It's about understanding the business, the people, the processes, and the decisions that ultimately determine whether technology makes an organization better.

An Interesting Gap in Wealth Management

After leaving Laird Norton Wetherby in 2025, I spent several months reconnecting with people across the wealth management industry.

I spoke with CEOs, COOs, technology leaders, advisors, consultants, and other industry professionals. Initially, those conversations were simply an opportunity to learn what was happening outside the organization where I'd spent the previous 12 years.

But I started noticing a pattern.

Many wealth management firms are wrestling with the same challenges I spent much of my career addressing.

Technology costs are increasing. Platforms don't always work together. Cybersecurity expectations are growing. AI is introducing new opportunities and new questions. And firms are trying to scale without adding unnecessary complexity.

Yet relatively few have dedicated senior technology leadership.

In many cases, responsibility for technology falls to the COO, an operations leader, or even a financial advisor who happens to be comfortable with technology.

These are capable people, often doing an excellent job. But technology is only one of their many responsibilities.

And while these firms have legitimate technology challenges, hiring a full time CTO isn't necessarily practical or justified.

There aren't many CTOs in wealth management. But there certainly isn't a shortage of CTO problems.

That observation became the foundation for Stack Strategy.

Why Stack Strategy?

I'm launching Stack Strategy with a relatively simple idea: wealth management firms should have access to experienced, independent technology leadership without necessarily having to hire a full time executive.

Not another software vendor. Not another managed IT provider. And not someone whose first recommendation is to replace everything.

Someone who understands how advisory firms actually operate, can help leadership make informed decisions, and can connect technology investments to business outcomes.

Sometimes that means developing a practical technology roadmap. Sometimes it's helping select a new platform, evaluating cybersecurity readiness, figuring out where AI makes sense, or guiding a complicated implementation. And sometimes it's simply having an experienced technology executive in the room to ask the right questions, challenge assumptions, and help a leadership team avoid expensive mistakes.

I've been on the other side of those conversations. I've managed the budgets, negotiated the contracts, worked through the implementations, dealt with the incidents, and lived with the consequences of decisions that looked great on paper.

That's the experience I'm bringing to Stack Strategy clients.

A Different Kind of Technology Advisory Firm

Stack Strategy is intentionally designed to be a boutique advisory business.

I want to work closely with a select group of clients, understand their businesses, and become someone they trust when important technology decisions need to be made.

Our services are built around the problems firms are facing today, from technology assessments and cybersecurity preparedness to AI strategy, vendor selection, implementation leadership, and ongoing fractional CTO advisory.

We also help advisors establish independent firms, bringing experienced technology leadership to the planning, platform decisions, and implementation challenges that come with launching an RIA.

The goal isn't to create more technology work.

It's to help firms focus on the right work, make good decisions, and actually move things forward.

What's Next

I've thought about starting my own consulting business at different points in my career. The timing never quite worked out, and there was always another interesting challenge to tackle.

But after spending so many years building technology capabilities inside a wealth management organization, I realized there was an opportunity to bring that experience to firms that might not otherwise have access to it.

That's what makes Stack Strategy exciting to me.

I get to continue doing the work I enjoy most: helping people solve problems, mentoring teams, making complicated decisions a little easier, and finding practical ways for technology to make businesses better.

If you're leading a wealth management firm, building an independent advisory business, or working through a technology challenge, I'd welcome the opportunity to connect.

Let's talk about what you're working on.

Trevor HicksFounder, Stack Strategy