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Dillon Schackmann
Licensed Sales Agent

A Personal Message from Dillon

Cell: 808.428.1029


  • LinkedIn

License & Credentials

  • HI Insurance License number: 440982

  • National Producer number:  17977028

  • AHIP Medicare + Fraud, Waste and Abuse Certified

Contracted Insurance Carriers

  • HMSA

  • UnitedHealthcare®

  • Humana

  • Ohana Health Plan

  • AlohaCare

  • GTL

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Get to know Dillon

As a Premier Benefit Consultant agent, Dillon Schackmann is here to help you understand all of your health insurance options and to provide excellent ongoing service once he assists you to enroll into the plan of your choice.  Dillon offers guidance for individuals with existing Medicare health plans, those new to Medicare as well as those preparing to retire and transition from employer based health coverage to individual coverage.  Phone or video conferencing consultations are available by appointment and free of charge.  Whether you are a Medicare beneficiary, employer, physician, guardian or anyone looking to understand the complexities of Medicare, contact Dillon and he will gladly assist you.

Dillon was born and raised in Honolulu, the only child to a hard-working, single mother. Dillon’s grandfather, who was a second-generation, Okinawan immigrant and former pig farmer, and his grandmother, a Catholic eucharistic minister, played a large role in helping to raise him. As a result of his multi-generational upbringing, Dillon was taught the importance of faith, hard work, integrity, and ‘ohana. Dillon was raised in Kalihi and was fortunate enough to be enrolled at Maryknoll Highschool, where he graduated in 2006.

Dillon obtained his health insurance license from the State of Hawaii in June of 2016 while working with special needs children for the Department of Education as an autism behavioral therapist. Dillon’s patience and ability to simplify, what would be complex and confusing information, lead him to being recognized as one of the top therapists in his field. However, Dillon had a feeling that there was still more he could do for his community. Hesitant to leave the children he had been working with for more than 8 years, Dillon decided to begin his career as a licensed insurance agent, but only part time.  Within a year, Dillon realized his true calling.  He discovered his affinity for assisting the Medicare beneficiaries of Hawaii in understanding and obtaining healthcare benefits. Moreover, he genuinely enjoyed helping them find security, comfort, and confidence in their healthcare choices.

Dillon finds gratification and pride in helping those less fortunate than him. He is a volunteer coach with Special Olympics Hawaii. He also offers his assistance to the homeless community at Punawai Rest Stop, River of Life Mission, as well as multiple foodbanks and soup kitchens around the island. Dillon has also been working closely with the Cancer Center of Hawaii and Hawaii Cancer Care for the past 4 years, in assisting all of their Medicare eligible patients.

When Dillon isn’t working, he enjoys fishing, traveling, trying new foods, and spending time with his family. Dillon also has a passion for plants and gardening and takes pride in his “green thumb”.

Medicare is intimidating and confusing to navigate alone. With so many different choices and annual changes, it can be difficult to know which plan is the best fit. As a trusted resource, Dillon guides his clients every step of the way. Dillon continues to serve his clients with unrelenting determination, integrity, and whole-hearted empathy. Dillon sees a little bit of his grandparents in every client he has the opportunity to work with, and treats them as if they were his own ‘ohana.

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