Silas Jessup, Medicare Insurance Agent

About Me

Silas Jessup has worked as an insurance advisor and consulted with individuals and small business owners since 2001. He helps clients protect their assets while also implementing strategies to mitigate rate increases and maximize any available tax advantages. Silas is also a recognized Medicare specialist. He partners with top insurance carriers to provide clients with private Health, Life, Supplemental, Long Term Care, Disability, and Medicare Insurance options.

Silas also serves as a Territory Vice President and Executive Sales Leader with HealthMarkets Insurance Agency. In these roles, Silas recruits, hires, trains, mentors, and motivates a team of over 100 insurance professionals. HealthMarkets advisors meet with clients by individual appointment to review their situation, analyze their options, and provide informed counsel.

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My Google Reviews

75 Total Reviews   (5.0 )

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Michael Slisher
May 28, 2026

This was our fourth (fifth?) year with Sondra and as usual, she was professional, personable, and a great asset for our insurance questions. Looking forward to our next appointment. (Can you believe someone would actually look forward to discussing health insurance?)

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Phil Taylor
May 27, 2026

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Steve Nichols
May 26, 2026

I'm so grateful for the Silas Jessup Agency, and especially for Sondra Gardetto. She guided us with real expertise, patience, and care. It means a lot to have someone so knowledgeable and trustworthy helping us.

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Phyllis Spanton
May 16, 2026

Silas has been our agent for over 15 years, yet we have never met in person! He has always been available for our yearly review and any other issues that come up. We feel like we know him and his family well. Our phone conversations are always professional, but also feel like we are catching up with an old friend. His staff have also been available and helpful. We began our relationship through a friend’s referral and we would never hesitate to refer his expertise to other friends.

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Michael Kramer
May 16, 2026

Silas and his crew are great to deal with they all treat like family they are vary professional and courteous