Meet Our Team

Sam Olson

Meet Sam Olson, the Medicare expert who’s simplifying the confusing world of healthcare for seniors in Napa Valley and beyond. With a passion for helping others and a keen eye for navigating the complexities of Medicare, Sam founded Sam Olson Insurance Services in 2019, driven by a mission to make healthcare accessible and understandable for everyone.

As an independent insurance agent, Sam represents over 20 carriers, providing recommendations tailored to each client’s needs. Specializing in Medicare supplement plans, he conducts personal interviews to analyze all available options and ensure his clients maximize their benefits.
Sam’s commitment to excellence has earned him recognition in the industry, including being named the Best Insurance Company in Napa County for 2023 and achieving the Highest Production Increase for United American Insurance in 2022. With over 50 five-star reviews on Google, his dedication to his clients is evident. He also contributes his expertise as a Medicare expert for Napa Spotlight Magazine.

For Sam, the joy of his work comes from the relationships he builds with his clients. Listening to their stories and sharing in their wisdom, he finds fulfillment in making a difference in their lives. While others may find the topic of Medicare daunting, for Sam, it’s an opportunity to connect with people and provide them with the peace of mind they deserve.

Outside of his professional endeavors, Sam is deeply involved in his community. He’s an active Rotarian for the Rotary Club of North Napa, where he served as Secretary from 2021 to 2023 and is currently President-Elect, set to become President in July 2024.

When he’s not busy serving his clients or giving back to the community, Sam enjoys spending time with his wife, Sarah, and their three beloved dogs, Penny, Max, and Arya.

Sarah Krupa

Administrative Assistant

Sarah Krupa is an Administrative Assistant at Sam Olson Insurance Services and is often the first point of contact for clients. With more than 20 years of experience in healthcare, Sarah brings a strong background in client service, care coordination, and administrative support to the agency.

Before joining the team, Sarah worked with the Department of Veterans Affairs as an Advanced Medical Support Assistant and Referral Coordinator, where she helped Veterans access specialty and urgent care in a timely manner. Her dedication to service earned her the “Going the Extra Mile Award.” Her background also includes experience as a Certified Medical Assistant, caregiver, mental health technician, and volunteer with the American Canyon Welcome Center.

Sarah holds a California Life and Health Insurance License and enjoys helping clients through education, clarification, and support. Her goal is to make clients feel heard, comfortable, and confident as they navigate their Medicare planning needs.

Sarah has lived in the Napa area for more than 15 years. Outside of work, she enjoys spending time with her husband, Derek, their family and friends, and their dog, Buddy. They especially enjoy getting outdoors and visiting places like Mare Island, the American Canyon Preserve, and Downtown Benicia.

Sarah believes that being of service to others is an important part of living a fulfilling life, and she brings that mindset to every client interaction.