Accurate Personalized Medicare Advice Without Getting on the Phone

The Pocket Protector is a smart, easy to use Medicare virtual assistant. Our interactive guide walks you through every Medicare decision step by step — asking about you, then personalizing a plan just for you, and clearly explaining the why behind every recommendation.
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Digitizing the $33-billion Medicare enrollment opportunity.

Our Technology: Making Medicare Simple

The Pocket Protector brings together doctor lookup, plan shopping, and prescription checks into one guided experience. TPP walks you through each step, then clearly shows you which options which option is the right fit for you and why.

Doctor Lookup

TPP doctor lookup screen

Plan Shopping

TPP Medicare shopping experience

RX Lookup

TPP prescription lookup screen

Our Team

Experienced team with deep industry experience and success
Jarret DiToro headshot

Jarret DiToro — CPO

Prior public & private CMO driving innovative growth of the largest publicly traded Medicare agency.
Michael Boshardy headshot

Michael Boshardy — CEO

Medicare attorney & compliance specialist.
Joe Wald headshot

Joe Wald — COO

Ten-year Medicare operator; built and ran high-throughput digital funnels for multiple agencies.
Joe Wald headshot

Patrick Kahn — CTO

Serial architect of AI-powered products; computer-science background and successful prior founder.
Collectively, we’ve built and scaled some of the most successful Medicare platforms in the U.S. — now we’re automating that expertise.

Comming Soon

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No spam, no calls - just smarter Medicare.