Christopher O'Kieffe
Founding Agent & Licensed Medicare Advisor
Meet Chris
Christopher O'Kieffe is a Founding Agent and Licensed Medicare Advisor at The Pocket Protector with more than 15 years of experience in sales and client advisory, and a sharp specialization in Medicare Advantage, Medigap, and prescription drug coverage. In 2024, Chris ranked in the top 10 out of roughly 1,000 agents nationally and earned back-to-back Presidential Trip awards — recognition reserved for the highest-performing Medicare advisors in the country.
Chris spent more than a decade in client-facing roles focused on service, retention, and conflict resolution before moving into Medicare — earning six consecutive Pillar of Excellence awards for outstanding client service along the way. That foundation translates directly into his Medicare practice: he doesn't just enroll clients, he builds plans they actually keep, because the fit is right from day one.
Chris is especially skilled with complex situations that other advisors miss or get wrong: veterans who don't realize their VA benefits count as creditable coverage, clients who lose Medicaid after a life event, new-to-Medicare beneficiaries shocked by cost differences from employer plans, and TRICARE coordination issues that leave people overpaying for months. He takes the time to untangle these situations and get clients to the right answer.
When Chris is not advising seniors or spending time with his wife and kids, he loves fishing.
Areas of Specialization
Client Success Stories
Veteran — VA + Medicare Coordination
Veteran Thought He Was Disqualified from Medicare Advantage
A veteran believed he couldn't enroll in a MAPD plan because he never had Part D or dental. He was also afraid of a late enrollment penalty. Chris confirmed his VA benefits counted as creditable drug coverage — meaning no penalty — and enrolled him in a plan with dental, vision, and hearing included.
Veteran — Out-of-Pocket Drug Costs
VA Didn't Cover Key Medications — Client Was Paying Cash
A veteran relied solely on the VA for prescriptions, but the VA wouldn't cover needed pain management medications. Chris enrolled him in a MAPD plan with Part D coverage for the drugs the VA wouldn't provide, while keeping VA access for everything else — eliminating the gap entirely.
Medicaid Loss After Home Sale
Lost Medicaid After Selling Home — Premiums Spiked
A client lost Medicaid after selling her house — the proceeds temporarily boosted her assets, triggering full Medicare premiums and IRMAA surcharges. Chris explained exactly why it happened, walked her through the SSA appeal process, and sent her the correct form to document the home sale as a one-time life event.
New to Medicare
New Beneficiary Shocked by Medicare Costs vs. Employer Plan
Peggy was new to Medicare and frustrated that Part B plus a supplement cost more than her employer plan. Chris reviewed her total cost picture and showed her that while premiums were higher, her actual out-of-pocket exposure was lower under Medicare — and a long-delayed surgery would be easier to get approved.
TRICARE Coordination
Client Overpaying Because Claims Weren't Going to TRICARE
A client was overwhelmed by medical bills. Chris discovered she had TRICARE but wasn't submitting claims for secondary coverage. He showed her exactly how to submit claims correctly, immediately reducing her financial burden.
Licensed States
Licensed in 24 states
Carrier Appointments
License Verification
National Producer Number (NPN)
19887558
Education & Credentials
- Niles North High School — Skokie, IL
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