Packed Up. Showed Up.
Built it.
I grew up in Iron River, Michigan. Upper Peninsula. The kind of place where winters are brutal, options feel limited, and you learn early that no one's coming to rescue you. You figure it out. Or you don't.
Where I Came From
Iron River, Michigan is a small town in the Upper Peninsula. The winters are long, the options feel limited, and the path out isn't obvious for most people who grow up there. A lot of people stay. Not because they want to — just because leaving takes more than wanting to.
I wanted out.
So I worked. Whatever I could find. Construction, fast food, manual labor. The kind of jobs that teach you things no classroom ever could — how to deal with difficult people, how to show up when you don't feel like it, how to figure things out without anyone walking you through it.
One of the stranger ones: I got paid to drive around to gas stations and restaurants and try to order alcohol to see if they'd card me. When they didn't, I handed them a violation. It's a funny thing to explain at a dinner party, but it was real work, and it paid.
I saved everything. After about a year, I had enough. I packed up and moved to Chicago.
The Mailroom
I grew up watching movies where the city felt like a whole other world — the skyline, the energy, people moving with purpose toward something. Chicago was that world. I wanted to be part of it.
I lived on the south side in the cheapest apartment I could find. No network, no connections, a resume that closed more doors than it opened. So I got a job in the mailroom for a document processing company in downtown Chicago.
That was the actual job. Sorting mail. Learning the floors. Figuring out how the building worked.
I paid attention to everything — who was busy, who was respected, how decisions got made. I kept showing up and doing more than what was asked. Eventually people started to notice.
The Moment Everything Clicked
Growing up, people used to tell me I'd either end up as an actor, a lawyer, or a salesman. I never really knew whether to take that as a compliment or a sideways comment about how I never stopped talking.
When I realized the mailroom was as far as I'd go at that company, I figured maybe I should finally listen. I didn't have time for law school and didn't have the money to try acting — so I started looking for sales jobs.
I started as a BDR. Cold calls, prospecting, getting hung up on — all of it. But I was good at it, and I moved up. Eventually I was managing other BDRs, which turned out to be the part I loved most. Watching someone who was nervous and raw start to find their footing, that was genuinely satisfying.
The accounts I was working weren't easy either. A lot of C-suite outreach — executives who had seen every pitch and had no patience for anyone who wasn't sharp. There's a real gap between a kid from Iron River who'd never sat in a boardroom and someone who can hold a conversation with a CISO or a VP of Engineering about their specific problems. I had to close that gap fast. I did it by learning everything I could about every product I sold and by caring more about solving the right problem than closing the deal.
I started doing well. Really well.
A Decade Of Building
Over the next ten years I worked across healthcare, cybersecurity, medical devices, SaaS, and events. Different industries, different stages, different problems. Each one taught me something the last one didn't.
The last stop before going out on my own was CyberRisk Collaborative. I built and managed CISO communities across the country, planned events, developed relationships, and drove revenue through memberships and sponsorships. One of our flagship dinner events went from averaging around $25,000 per event to over $70,000 after I took over. At one point I oversaw 9 quarterly dinners and 3 annual Summits.
None of that happened because I had a formula. It happened because I built real relationships with people.
The Day The Decision Was Made For Me
In a market where mass layoffs had become almost routine, I wasn't immune. It happened to me too.
Part of me was genuinely sad about it. I liked what I was doing. I was good at it, and I cared about the work. Losing that wasn't nothing.
But another part of me felt something unexpected — relief, maybe, or something close to it. I'd spent years watching the same sales problems repeat themselves across every company I'd worked for. Founders who couldn't get out of their own deals. Teams without a real process. Revenue that felt random no matter how hard everyone worked. I knew how to fix those things. I'd been doing it in one form or another my whole career.
Getting laid off forced a decision I might have kept putting off. So I made it. I started Stafford Strategies — not as some bold leap, but because betting on myself made more sense than waiting for someone else to decide what came next.
What I Believe
Sales is simpler than most people make it.
You shouldn't have to convince anyone to buy from you. If it's the right fit, it should feel like an obvious yes for both sides. The moment you're working to talk someone into something, you've already lost — and candidly, you probably should.
The best sales leaders don't create pressure. They create trust and clarity so that the right decision becomes obvious.
The Mission Now
Stafford Strategies exists to give founders and business leaders something most companies don't have until they're much further along — sales leadership that knows how to build, manage, and scale a revenue function from the inside.
This isn't consulting from a distance. I sit in the seat. I manage the team, run the pipeline reviews, build the playbooks, coach the people, and drive the outcomes. The same work a VP of Sales does — without the full-time overhead and without making myself a permanent fixture in your business.
I know what a well-run sales org looks like. I know what quietly breaks one. And I know the difference between motion and momentum.
I don't want to be anyone's long-term crutch. I want to build something that runs without me. When that happens, the work is done.
If that's where you're trying to get, you know where to find me.
Let's build something that works.
Book a free consultation. No pitch. Just an honest conversation about where you are and whether we can help.