My approach
How I work with clients
I don't sell, I review. Every call starts with your prescriptions, your doctors, and your real budget — then we look at what actually fits.
Licensed Medicare Caddie
Jake Tripp
Licensed Insurance Agent
Insurance agent who left another firm to work with veterans full-time. Focused on unhurried annual reviews and prescription-list matching.
VeteransMedicare AdvantagePrescription Drug CoverageAnnual Reviews
- States licensed
- Multiple states — ask for current list
- Languages
- English
Biography
About Jake
Jake started his insurance career somewhere else and felt unfulfilled for years. Everything changed the day he sat across from a veteran and walked him through benefits he didn't know he had — often with no additional cost.
He made the switch shortly after. Today Jake specializes in that exact conversation: slow, clear, no pressure, and always tied back to the client's actual prescription list rather than whatever plan happens to pay the highest commission.
In their own words
Why I became a Medicare Caddie
"The best part of this job is being the person someone can call every October, not just at enrollment. That's the version of insurance I always wanted to practice."
Who I love helping
The people I do my best work for
Veterans who've been on the same plan for years and aren't sure whether it's still the right one — plus their spouses, who usually have questions of their own.
Favorite part of the job
What keeps me coming back
Getting the October phone call from a returning client. That's the real job — not the initial enrollment.
Fun fact
A little about Jake off the clock
Left another insurance job because it didn't feel like the work was really about the client. This one does.
🏌️ Jake's Caddie's Tip
"Your prescription list changes. Your plan should get reviewed every year to match it — not the other way around."
Ready to work with Jake?
No pressure, no scripts — just a plain-English walkthrough of what fits your situation.
Medicare Caddies is an independent insurance agency. We are not affiliated with, endorsed by, or connected to the U.S. government, the federal Medicare program, or the Centers for Medicare & Medicaid Services (CMS). We help compare Medicare Advantage plans from the insurance companies we represent, and we don't offer every plan available in your area.