Bricklayer. Soldier. Exec. AI Strategist. The Career Nobody Would Have Written.
My resume doesn't follow a straight line and never has. Here's why I think that's exactly why it works.
May 24, 2026
Leadership, Cross-Industry, Military, AI Strategy, Career
The Reaction
When people look at my resume for the first time, I can usually pinpoint the exact moment they get lost. It happens somewhere between "stone mason" and "Lieutenant Colonel" — or maybe between "Waste Management" and "AVP, Financial Technologies at KKR." The brow furrows. The head tilts. And then someone says some version of: so how exactly did you end up here?
The honest answer is that none of it was planned. Not a single transition was the result of a five-year career strategy or a deliberate pivot toward some predetermined destination. Every move happened because a door opened, I was prepared enough to walk through it, and I had the sense to recognize that what was on the other side was worth exploring — even when it didn't match what came before.
The Thread
There is a thread. It just doesn't look like a straight line.
Every chapter of this career built something that the next one needed — even though I couldn't see that in real time. The masonry taught craft and standards. The military taught leadership under pressure. Retail and distribution taught operational scale. Waste management taught process rigor under regulatory constraint. Financial services taught enterprise complexity. And all of it — every seemingly disconnected chapter — converged into the AI strategy work I do now in a way that makes the whole path look almost intentional in retrospect.
It wasn't. But the pattern is real.
The Foundation: Military and Masonry
The Army came first — April 2000, right hand raised, no real understanding of what 26 years of concurrent service would eventually look like alongside a full civilian career. What the military gave me immediately was a framework for operating under pressure with limited resources toward a defined objective. Decision-making under ambiguity. Leadership without always having positional authority. Accountability with no room for excuses. Those aren't soft skills on a resume — they're operational instincts that transfer into every room I've ever walked into since.
In 2005, I was coming off a deployment and approaching my final semesters at UMass. I'd accumulated deployment income with nothing to spend it on, and I needed to figure out what came next. Masonry was the natural answer — not because of some career plan, but because I'd been mentored in stonework as a teenager by one of my paper route customers. I knew the trade. I had the capital. I started my own business.
Stone masonry teaches you something that most professional environments can't replicate: your output is permanent, visible, and either right or wrong. You either laid it level or you tore it out and started over. There was no hiding mediocre work behind a well-formatted slide deck. That standard — build it right or don't build it — embedded itself so deeply that I still apply it to everything I touch.
The Pivot Nobody Planned: Construction to Corporate
A stonework project led me to a Home Depot construction site. That proximity led to a conversation. That conversation led to an application. And suddenly the BBA I'd just finished had somewhere to land.
I hung up the sledgehammer and stepped into operations management at Home Depot's distribution network. The jump sounds dramatic from the outside — mason to corporate — but the underlying work wasn't that different. Logistics is logistics. Moving materials efficiently, managing people under time pressure, maintaining quality standards while hitting volume targets. The scale was different. The principles were identical.
Scale: Retail and Distribution
Home Depot introduced distribution at scale. Target introduced retail operations at a level of organizational complexity that rewired how I thought about leadership entirely. As an Executive Team Leader, I was managing a floor of people across wildly different situations, skill sets, and competing priorities — with real pressure and narrow margins for error. Retail stripped away every theory about management I'd ever encountered and replaced it with operational reality.
You learn what actually matters when you're running a team on a Sunday night with a system outage and a line of customers out the door. The answer is never in a playbook. It's in the person who can stay calm, prioritize in real time, and communicate clearly enough that everyone around them knows what to do next. That capability isn't something you learn in an MBA program. You earn it under pressure.
The Data Awakening: Waste Management to Global Atlantic
Waste Management's National Accounts team put me inside enterprise operations with serious consequence — environmental compliance, regulatory risk, federal exposure. Process discipline wasn't optional. And managing a $22M national portfolio meant I was living inside operational data every single day: performance metrics, cost-savings analyses, compliance tracking, renewal forecasting.
That's where the data instinct sharpened. Not through a course or a certification — through daily necessity. I was swimming in operational data, and I started noticing patterns in how organizations used it (or didn't). That perspective followed me to Global Atlantic, where I joined as a Retirement Operations Manager and immediately started pulling the same thread: where is the data, who's looking at it, and why isn't it being used to drive better decisions?
The Accidental Technologist
The Salesforce story is probably my favorite because it's the most accidental.
I was the operations team's best representative on a cross-functional Salesforce Working Group — a seat I held because I understood the business processes being configured, not because I had any technical credentials. The group was led by the VP of Salesforce Engineering. Over months of working sessions, we built a strong working relationship. He knew I was effective in my operations role and that I understood both the business logic and the platform capabilities at a level most ops people don't.
One day, half-joking, I said: "If you ever have an AVP spot open on your team that I could fill, I'm in."
Three weeks later, he asked me to join his team.
No formal application. No recruiter. No technical interview. Just months of demonstrated competence in a cross-functional setting, a relationship built on mutual respect, and the willingness to say out loud what I wanted — even as a joke.
That moved me from operations into financial technology. From there, I taught myself Salesforce administration, then architecture, then the AI capabilities being built on top of the platform. When generative AI arrived, I went all in — not because someone told me to, but because I could see where the entire landscape was heading and I wanted to be ahead of it rather than reacting to it.
What the Non-Linear Path Actually Built
Every chapter handed me something specific that the AI strategy work I do now requires daily:
The mason built an intolerance for mediocre output and an understanding that foundations have to be right before you go vertical.
The soldier built decision-making under ambiguity, leadership across organizational boundaries, and the ability to execute when the plan falls apart — which it always does.
The distribution and retail operator built an understanding of how large, complex organizations actually function at the ground level — not how they're supposed to function on an org chart, but how they actually behave when the pressure is real.
The waste management executive built process discipline under regulatory constraint and a comfort with operational data as a decision-making instrument.
The fintech operator built enterprise-scale technology fluency and the ability to translate between business stakeholders and technical teams.
The continuous improvement practitioner built a systematic methodology for identifying and eliminating inefficiency — Lean, DMAIC, process mapping — that predates the AI work by years but integrates with it seamlessly.
None of these were acquired with the intent of building an AI strategy career. But collectively, they produced something that a single-track background simply cannot replicate: range. The ability to walk into any industry, any organizational structure, any operational environment — and understand within the first conversation where the friction lives, why it exists, and what's actually needed to resolve it.
The Advantage of Breadth
I've watched highly specialized people walk into complex, ambiguous, cross-functional problems and freeze — because they've never had to operate outside their lane. That's not a knock on specialization. It's just what deep specialization sometimes costs.
AI strategy in particular rewards breadth. The work isn't purely technical. It isn't purely operational. It isn't purely about change management or leadership or process design. It's all of those things simultaneously — and it requires someone who can hold all of them in their head at once while making decisions that account for each dimension.
That's not a skill you develop by spending twenty years in one domain. It's something that gets built — accidentally or otherwise — by spending time in many.
The Cost of the Unconventional Path
None of this comes without trade-offs.
The non-linear career means constantly explaining yourself. Every new conversation — with a recruiter, a hiring manager, a potential partner — starts with the same fifteen seconds of visible confusion. The resume doesn't scan the way people expect. There's no clean narrative that fits into a LinkedIn headline or a recruiter's keyword search. You don't get the benefit of the doubt that comes with "fifteen years in financial services" or "career military officer." You have to earn the credibility from scratch in every room because nobody's going to hand it to you based on pattern recognition.
That gets tiring. It never fully goes away. And there are absolutely doors that stayed closed because someone looked at the path and couldn't make it make sense fast enough to keep reading.
The Juggle
Running a 26-year military career concurrent with every single civilian role on this resume is its own category of challenge. Deployments that pull you out of civilian work for months. Drill weekends that consume time your peers spend with their families or advancing their civilian careers. The constant cognitive switching between two entirely different organizational cultures, leadership contexts, and operational environments.
The Army doesn't pause because your civilian job is demanding. Your civilian employer doesn't always understand why you're gone for three weeks. And your family absorbs the cost of both. Making all three work simultaneously for over two decades requires a level of time management, prioritization, and tolerance for sustained discomfort that I wouldn't wish on most people — even as I wouldn't trade it for anything.
What Specialization Offers That I Don't Have
I'll be direct about this: the generalist path means I will never have the depth of someone who spent fifteen years doing one thing. There are technical domains where a specialist will outperform me. There are institutional relationships that only form over decades inside one organization. There's a credibility shorthand that comes with deep domain expertise that I simply don't carry.
The advantage I bring is different — it's pattern recognition across domains, adaptability to unfamiliar environments, and the ability to connect ideas that don't usually share a room. But I'd be dishonest if I pretended the non-linear path doesn't have real costs alongside the benefits. It does. The question is whether what it builds is worth what it costs. For me, the answer has always been yes — but I understand why most people don't choose it.
Reflection
I didn't build this career on purpose. I built it by showing up, staying curious, and never turning down an opportunity because it didn't fit the last chapter. The path from stone mason to AI strategist doesn't make sense in a linear narrative — but it makes perfect sense as a compounding series of capabilities, each one building on everything that came before.
If your own path already looks unconventional from the outside — if you're questioning whether the detours were mistakes — they probably weren't. The thread is there. You'll see it eventually. And when you do, you'll realize that the very thing that made your resume hard to explain is the thing that makes you impossible to replicate.
The Principle
Stay disciplined. Stay curious. Keep building. And when someone asks how you ended up here, don't apologize for the path. Explain why it's exactly what the work requires.
Cross-industry experience, military-grade operational discipline, and applied AI strategy don't often come in the same package. That combination is exactly where I do my best work — and where the organizations I work with tend to find the most untapped value.