If you built it from scratch today, would it be the same?
The company. Your role. The way you lead. The life around it. More of it likely accumulated than consciously chosen.
I work with founders and CEOs navigating consequential change, helping them get clear about the future they want, become the leader they need to be, and evolve the company for what comes next.
The ground is moving.
AI is reshaping how work gets done, where value is created, and what companies — and people — are capable of. Geopolitical and policy volatility are making the future harder to predict. And a changing workforce is bringing new expectations about work, leadership, and what people are willing to give their lives to.
For founders and CEOs, standing still isn’t an option. You’re being asked to make bigger decisions with less certainty — about strategy, your team, your board, AI, capital, growth, and exit.
What does this next stage require — from the company and from you?
I know this one from the inside.
I’m Matt Prindiville. Years ago, I co-founded and ran Upstream, a national change agency at the center of U.S. packaging and plastics policy. By every external measure, it looked like wild success. But inside, I was overwhelmed, running on empty, and not leading the way I knew I could. My team felt it. So did my family.
So I started changing how I led and how I lived. For the better part of a decade, I read, trained, worked with coaches, and tested what I was learning under pressure. I kept what worked and dropped the rest.
Some of it was as simple — and as hard — as walking out at 5:30 to coach my daughter’s basketball team, and actually being there when I arrived.
Later, I became CEO of CLYNK when the business was under real strain. I put those lessons to work: getting clearer about my role, building a stronger leadership team, and changing how decisions got made and how the company operated. I stopped sitting in every sales call and started showing up where only I could make a difference.
We turned the business around, grew revenue to $30M in three years, doubled our store footprint, and ultimately sold the company to TOMRA. I did some of the best work of my career. And I lived and led differently while I did it.
Now I help founders and CEOs do the same.
Ways to work together
Three ways in, depending on what's actually going on.
CEO Advisory
“I’m too close to see it. I need someone who’s been in the chair.”
An experienced CEO in your corner.
A private advisory relationship for founders and CEOs. We start with what's in front of you: what you're trying to build, where you're stuck, and the decisions that matter most. The acquisition offer, the exec who isn't working out, how AI should change the way your company runs, the hard call you keep circling. As we work through what's immediate, we step back to the bigger design: what only you should own, what your team should own, and what kind of life the job has to fit inside.
Someone who’s founded, owned, and run companies — and will tell you the truth when you need to hear it.
Leadership Team Work
"We need to get everyone in a room and figure this out."
The right people. The real problem. Enough time to solve it.
A strategy that needs to evolve. A leadership team that needs to work as one. A decision that keeps getting stuck. A company entering a new stage. AI changing which work people should do, what should be automated, and how it all flows. An offsite that needs to produce more than good conversation. I design and lead focused work with CEOs and leadership teams on the questions that drive results: a vision and values the whole team owns, how the team needs to evolve to get there, and how the company executes to achieve it.
“I'm leaving the life I want, and the leader I could be, on the table.”
ThriveLab
Build the foundation to go further.
A 12-week experience for ambitious founders and leaders who know going further means changing how they live and lead. We work on what's underneath: your vision, the beliefs and patterns you're carrying forward, how you lead under pressure, and the role work should play in your life. It starts with an immersive retreat, then continues through a small cohort, a peer partner, and private sessions with me. You leave with a Personal Operating System you've tested in real life, and a process to design every stage that follows.
Free resource
What's keeping you up at night?
The 3 A.M. List is a free 30-minute exercise built on the three questions I start with in every advisory relationship.
Get the list →“I’ve seen Matt drive breakthrough innovation, navigate investor dynamics and operational complexity, lead a team through an acquisition, and handle challenges that would overwhelm most leaders. His ability to set a vision, inspire a team, maintain perspective, and make hard choices is remarkable. Anyone who has the opportunity to work with Matt will get an incredible coach and partner.”
— Susan Hunt Stevens, Founder, Tessi · Previously WeSpire (acquired by Bonterra)
“I hired Matt to succeed me as CEO of CLYNK — and in less than three years, he grew the company faster than at any time in its history, positioning it as a dominant force in a volatile, quickly-evolving marketplace. His innovation was only surpassed by his skillful leadership managing and motivating a rapidly expanding workforce.”
— Clayton Kyle, Founder, CLYNK · Executive Chairman
key organizations i've worked with include
Board Service
I've sat on every side of the boardroom table.
I bring an operator’s perspective to the boardroom. I’ve founded and led organizations, reported to boards through a turnaround, rapid growth, and an acquisition, and worked at the intersection of business, policy, and systems change for more than two decades.
I understand the relationship between a board and CEO from both sides — where a board can add real value, where it can get in the way, and what leaders need when the stakes are high.
I serve selectively as an independent director for founder- and family-led businesses, PE-backed companies, and organizations where my experience in growth, leadership, circular economy, packaging, and environmental services can be useful.
“In 45+ years in business, I've worked with and been exposed to a number of top-talent executives. In my opinion and experience, Matt Prindiville is in the very top of that class.”
— Bob Schools · Former SVP of Retail Operations, Hannaford Supermarkets · CLYNK Board Member
featured in
Essays
Notes on the work
I spend my time with founders and CEOs in the moments when the old way of operating stops working and a new path is required: growth, pressure, hard decisions, changing roles, and the life around all of it.
Every couple of weeks, I write about what I'm seeing: patterns worth noticing, ideas worth testing, and questions worth thinking harder about.
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One essay every couple of weeks. Free. Unsubscribe anytime.
New here? Start with the 3 A.M. List →
