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About Cypress Jet

I didn't start this company to sell jet cards. I started it because clients kept getting sold, instead of served.

I'm Steve Simard. Before private aviation, I spent five years in the United States Marine Corps and more than fifteen years building relationships in technology sales. Those experiences taught me two different sides of trust.

The Marine Corps taught me about standards: prepare for what can go wrong, pay attention to the details, take responsibility for the outcome, and when people are counting on you, execute.

My career in sales taught me about relationships: listen before you talk. Remember what people tell you. Don't waste their time. Tell them the truth, including when the better answer isn't the one that makes you the most money.

Then I entered private aviation and saw an industry that was exceptionally good at providing access to extraordinary aircraft, but often surprisingly transactional in the way it served the people flying on them.

I thought those clients deserved both.

That's why I built Cypress Jet.

Steve Simard Founder & CEO, Cypress Jet
Steve Simard, Founder & CEO of Cypress Jet

The standard doesn't change under pressure.

I enlisted in the Marine Corps in 2001, a few months before September 11th. What I thought I'd signed up for and what the next five years actually required of me turned out to be very different things.

I served two combat tours in Iraq, both of which I volunteered for. During the first, I served with Security Forces, helping establish and maintain perimeter security for a forward operating base. During the second, I returned to my trade as a T-58-GE-16 engine mechanic, performing field maintenance on CH-46 engines and rotor blades in desert conditions far removed from a hangar back home.

Some of what we encountered hadn't been contemplated in the existing procedures, so I helped develop maintenance practices specifically for operating in that environment. I was promoted to E-5 in three and a half years.

That experience gave me a standard I've carried with me ever since: prepare thoroughly, pay attention to what others miss, take responsibility, and perform when people are counting on you.

The aircraft doesn't care about excuses, and neither do the people counting on it.

The Marine Corps calls its core values honor, courage, and commitment. What two combat tours taught me was how those values translate when circumstances are difficult, the stakes are real, and the plan changes.

That's the standard I brought with me when I left.

Then I learned the other side of trust.

I spent the next fifteen-plus years in technology sales, working with executives, founders, and other people whose time was valuable and whose tolerance for a sales pitch was understandably low.

I learned pretty quickly that the best relationships weren't built by selling harder.

They were built by listening.

Remember what someone told you the last time you spoke. Understand what matters to them before recommending something. Don't make them repeat themselves. Don't waste their time. And tell them the truth, even when the truth isn't the answer that makes you the most money.

Do that consistently enough, and something changes.

"You stop being someone they buy from. You become someone they call."

That distinction ended up mattering a lot when I found private aviation.

Private aviation showed me what was missing.

I entered the industry three years ago, almost by chance. I was ready for something new after technology sales, and the fit was immediate.

I learned the aircraft, the operators, the economics, the safety standards, and the mechanics of charter. But the part that came most naturally wasn't finding airplanes. It was the client relationship.

And something kept happening.

Clients who had flown privately for years started calling me directly. They stayed with me when they had plenty of other options. They told me things that had nothing to do with an itinerary because they knew I'd remember why those things mattered the next time they called.

Some eventually told me I should start my own company.

They weren't asking for another charter broker. They were asking to keep the relationship.

The longer I worked in private aviation, the more clearly I saw the disconnect. These were people who could access almost anything, flying on aircraft that represented the highest end of travel, yet the relationship surrounding the experience could still feel remarkably transactional.

A different representative. The same questions again. Another quote. Another trip. Start over.

I thought private aviation could be better than that.

So I built Cypress Jet.

Cypress Jet brings together the two sides of trust I've spent my career learning.

The Marine Corps taught me the standard: be prepared, take responsibility, and execute when people are counting on you.

Fifteen years in sales taught me the relationship: listen, remember, tell the truth, and earn the next call.

Private aviation showed me where both were needed.

That's what we're building here.

We want to know how you like to fly and which aircraft you don't. Who usually travels with you. Your dog's name. Whether you care more about finding the smartest value or getting the newest aircraft available.

And we want to know the things that aren't really about aviation at all.

Maybe there's a meeting you absolutely cannot miss. Maybe you're making the same trip every week for a reason you don't want to explain every time you call. Maybe your arrival time matters more than usual because someone is waiting for you on the other end.

Those details are part of the trip, too.

The longer we work together, the less of that you should have to tell us again.

5 YEARS

United States Marine Corps

Two voluntary combat tours in Iraq: perimeter security, then CH-46 field maintenance. Promoted to E-5 in 3.5 years.

15+ YEARS

Built on relationships

A career in technology sales spent earning trust with the same kind of clients I serve today.

3 YEARS AGO

Moved into private aviation

Trained, then outpaced peers with years more tenure by building my own approach on that foundation.

NOW

Cypress Jet is founded

Built around one standard: put the client first, every time, without exception.

What working with Cypress should feel like.

You should have someone who knows you when you call.

You should get a recommendation, not a pile of aircraft options you're expected to sort through yourself.

You should be told when spending more is worth it, and when it isn't.

You should be able to say, "Same as last time," and have that mean something.

And when something changes at the last minute, you shouldn't be calling around trying to solve an aviation problem yourself. That's when having someone who knows you and your trip matters most.

Most of all, you shouldn't have to manage the relationship.

Remembering the aircraft you like, the catering you don't, the people who travel with you, and the one thing that would ruin the trip if we got it wrong, that's our job to carry, not yours to remind us of.

In My Own Words

"I think the best service is the service you eventually stop noticing. You don't have to remember who to call, explain how you like to fly, or wonder whether someone is handling the details. That's our job. The longer we know you, the less you should have to ask."

STEVE SIMARD, FOUNDER & CEO

The luxury of being known.

You already fly private because your time matters. Your relationship with your aviation company should respect it, too.

Start with one trip. We'll take it from there.