A Founder's Perspective: The Shift We're In - and What it Requires

A Founder’s Perspective: The Shift We’re In—and What It Requires

April 2026 — From the Desk of Cheryl Grimaldi

I’ve spent over 30 years in executive search, much of that time working closely with family offices, principals, and senior leadership teams.

And recently, I’ve found myself more energized than I’ve been in years.

That made me pause.

Because energy at this stage doesn’t come from pace—it comes from relevance.

The Realization

I’ve always been drawn to environments where something is being built.

Where decisions matter.
Where there is movement.
Where the stakes are real.

And right now, it feels like we’re all living in that kind of moment.

A Defining Moment for Family Offices

What’s happening in the family office space right now is not a startup phase.

It’s something much more significant.

It is one of the fastest-growing and most rapidly evolving sectors in the world.

We are seeing:

• Increased sophistication in operations
• Greater demand for top-tier talent
• More complex investment and governance structures
• A heightened need for trusted advisors and operators

This is expansion at a high level—and it requires a different caliber of thinking.

The Role of AI in This Growth

At the same time, AI is accelerating how these organizations operate.

Not loudly—but meaningfully.

How information is processed.
How decisions are made.
How lean teams create outsized impact.

In environments where discretion, efficiency, and trust are paramount, this shift is critical.

My Relationship With Technology—Then and Now

Historically, technology has not always come easily to me.

There have been very real moments in my career where I’ve been in tears trying to get something as simple as a video call to work—knowing a client was waiting, feeling the pressure build, hands shaking as I tried to troubleshoot in real time.

And then stepping into that conversation not fully present.

Those moments shape how you experience work.

Why This Feels Different

This is why AI has been such a shift for me.

It feels intuitive.
It removes friction instead of creating it.
It enhances clarity instead of complicating it.

For the first time, I feel like I have a tool that allows me to fully express the depth of experience I’ve built over decades in this industry.

And I’m not just enjoying it—I’m absolutely in love with it.

What We’re Seeing in the Market

Across our recent retained searches, one thing is clear:

AI fluency is becoming a baseline expectation at the senior level.

Not as a technical specialty.

As a way of operating.

Leaders are increasingly expected to:

• Understand how AI impacts their function
• Integrate it into decision-making
• Use it to drive efficiency and insight

In our most recent searches, AI exposure has been a consistent requirement.

Those who lean into it are moving forward quickly.

Those who resist it are creating distance between themselves and the market.

Unlocking What Comes Next

There is a depth of perspective that comes from doing this work for over three decades.

But it’s more than experience.

There’s so much in my soul—and I know I still have so much to give.

AI is allowing me to deliver that more clearly, more efficiently, and with greater impact—for the families, executives, and teams we serve.

Responsibility at This Stage

At this stage in my career, I feel a deep responsibility:

• To the families and principals who trust us
• To the executives we place into critical roles
• To the teams we help build
• To the community we’ve developed
• And to my family

To stay ahead of what’s changing.
To remain clear in moments of complexity.
And to guide hiring decisions with both perspective and precision.

Final Thought

This is not a moment to hesitate.

It’s a moment to engage—with clarity.

The family office space is expanding, evolving, and becoming more sophisticated by the day.

And those who adapt with intention will define what comes next.

Anton Everest Executive Search

Strategic hiring for family offices and leadership teams navigating growth

Cheryl Grimaldi, CPC

President/Founder

Anton Everest 
970.390.0773
cgrimaldi@antoneverest.com