Melissa Andrews is your local health insurance expert. With 20+ years in the health insurance industry, she brings knowledge and education from many areas. Her career began as a benefits administrator for a software company in Boulder, CO. It was there that she discovered a unique love of benefits, and paired it with a passion for helping others. She enjoys the complexities of health insurance and is happy to help others navigate through their various options.

Melissa spent several years working in Human Resources (HR) as a Benefits Administrator, but it wasn't until she returned to Wisconsin in 2013 that she discovered how helpful she could be to those seeking health insurance outside of traditional benefits offered through an employer. She became the Elder Benefits Specialist (EBS) for Door County and worked for the Aging & Disability Resource Center (ADRC). In this role, she had the honor of meeting several local residents and assisting them, and their families, with accessing benefits.

This role was mostly education and assistance, so in 2016 Melissa decided to take the leap and become a licensed health insurance agent so that she could offer more services to her community. Melissa worked for a local insurance agency to learn the ropes and in the fall of 2018 she decided to take it solo. Olive Benefits LLC was born and has been growing every since!

Annika VanAlstine joined the team full-time in May 2024. She has assisted on a part-time basis during prior open enrollments, but now she is with us daily to keep the office moving along smoothly. She is an avid learner and enjoys helping others, too. She is ready and willing to assist you with any basic questions or issues.

Our mission at Olive Benefits LLC is to educate, empower, and advocate for all Wisconsin health insurance consumers. Melissa is independently contracted with several insurance companies to ensure our ability to offer a variety of products to meet your health insurance needs. Whether you are seeking education on your options, exploring the possibility of change and want to know how health insurance will impact you, looking for short-term medical insurance, or needing to learn more about longer term options, Like Medicare; we are here to help you every step of the way.

There is never a fee for our services or an obligation to enroll. Our goal is to save you time, money, and frustration throughout this process, as well as be there to help you when questions arise.

Owner & Agent

Administrative Assistant

Olive Benefits is an independent health insurance agency located in Sturgeon Bay, WI. We provide education & assistance to individuals on their health insurance needs. We are contracted with several insurance companies with various products available so that we may offer you a variety of options to ensure the most comprehensive coverage for your unique situation.

There is never a fee for our services or an obligation to enroll. We aim to educate, empower, and advocate for all Wisconsin health insurance consumers. We are compensated for our services via commissions paid by the insurance companies based upon secured contracts.