Join the Team

Are you looking for an exciting opportunity to join a dynamic team in the insurance and financial planning industry? Winsor Trust & Financial is currently seeking remote sales employees to be part of our growing business.

Young, Hungry, and Searching for More? This Is Your Tribe.

Let’s be real for a minute.

If you’re tired of dead-end jobs, college debt, or just feeling stuck with no clear direction… you’re not alone.

Maybe you’ve got that fire inside—but no outlet to release it. Maybe you’re craving something more than just punching a clock and trading time for a paycheck. You want real money, real freedom, and a team of people who push you to become your best.

Welcome to the opportunity you’ve been searching for.

This Isn’t Just a Job—It’s a Brotherhood Built for Winners

We’re building a tribe of driven individuals who are done living average lives. We don’t make excuses—we make progress. And we’re doing it through one of the most powerful and recession-proof vehicles out there: remote life insurance sales.

This isn’t MLM. It’s not some “get rich quick” play. This is real business. Real work. Real results.

And the best part? It’s 100% remote. That means no suits, no commutes, and no begging your boss for time off. You work from wherever you are—and you earn based on your hustle and your heart.

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What We Offer:

✅ 6-Figure+ Potential in Year One

We don’t guarantee easy—but we do guarantee a proven system. If you show up coachable and hungry, it’s absolutely possible to hit $100k+ in your first year. Some do it much faster.

✅ Mentorship from Elite Producers

You won’t be tossed into the deep end alone. You’ll be trained and mentored by some of the best in the industry—people who’ve already built seven-figure businesses and know exactly what it takes.

✅ A Brotherhood, Not a Boss

This isn’t a job. This is a movement. We believe in brotherhood, accountability, and calling each other higher—not managing from a distance. You’ll find yourself surrounded by others chasing greatness, just like you.

✅ Freedom + Purpose

Make money. Change lives. Build a business that you own and can be proud of. We’re not here to just make sales. We’re here to help people protect their families, and in the process, create generational change for ourselves and others.

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Who This Is For:

    •    Anyone pissed off for greatness with something to prove.

    •    Ex-athletes, military, door-knockers, or anyone with grit.

    •    You’ve got the drive, but need the vehicle.

    •    You’re coachable, competitive, and ready to go all-in.

    •    You want a tribe that pushes you, checks you, and has your back.

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Let’s Be Honest…

You’re not going to become a millionaire by doing the bare minimum. But if you’re willing to put in the reps, follow the system, and stay committed—you can build something most people only dream about.

If you’ve ever thought to yourself, “There’s gotta be more than this,”—this is it.

Not everyone’s cut out for this. But if you are? We’ll change your life. Not just financially, but mentally, physically, and spiritually.

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Ready to Join the Tribe?

We’re actively looking for the next wave of warriors— ready to fight for a better life, a better future, and a better version of themselves.

📲 Apply now, get on a quick call, and let’s see if this is the right fit for you.

You bring the fire. We’ll bring the system. Let’s build something legendary.