
Meet Our Team
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Jarret DiToro
Jarret has been involved in Medicare since 2018, specializing in uncovering benefits that many Medicare beneficiaries may not realize they’re eligible for. Jarret takes his mission seriously, making sure people are as knowledgeable as possible around what they qualify for. He researches which insurers are living up to their obligations, and what consumers need to know to make sure they don’t get taken advantage of. Beyond Medicare, Jarret is on a mission to hike through every major national park in America.

Michael Boshardy
For the past decade, Michael has established himself as a prominent regulatory attorney specializing in Medicare. He has successfully led Legal and Compliance divisions for various organizations focused on senior health, managing operations to design and implement programs tailored to beneficiaries and patients. Drawing on his deep expertise in navigating highly regulated markets, Michael plays a key role in advancing the goals of The Pocket Protector’s clients across the industry. He holds a JD from the University of Wisconsin and a BA in Economics from the University of Illinois.When not chasing after his toddler, he enjoys playing tennis and grilling in the little free time he finds.

Joe Wald
Joe has been working in the Medicare industry since 2017 with a specialization in digital marketing, and has proven experience leading marketing efforts and being an innovator in the space . He is passionate about simplifying Medicare into ways that help individuals navigate the Medicare maze with ease, confidence, and a sense of security. His approach combines innovative digital strategies with a deep understanding of consumer needs, ensuring every interaction empowers individuals to make informed decisions about their Medicare coverage. Outside of his work life, Joe is an avid 16 inch softball player and enjoys riding his bike around the beautiful city of Chicago.

Reid Cleveland
Reid Cleveland, serving as a Data Analyst at The Pocket Protector, brings a robust skill set in executing digital marketing campaigns for health and life insurance products. Reid meticulously analyzes market trends to optimize targeted marketing strategies. With a sharp focus on data, he manages databases for efficient AI utilization and rigorously tests in-house AI systems for prompt accuracy. Reid's collaborative approach ensures compliance with industry regulations, while their keen insights improve marketing performance through thorough KPI evaluations and strategic reporting.