Our Team

Meet your local insurance experts.

Outstanding service starts with an outstanding team. Meet the real people behind Safe Harbor Insurance.

Leo Michael and grandsonleoLeo G Michael

Principal, Licensed Agent: Property & Casualty, Life & Health



Leo has been with Safe Harbor since 2003, and has been a part of the Friday Harbor community for more than 40 years. He and his wife, Chris, moved back to the home of his alma mater to raise their three children in 1999. Leo values service to his community, time with his friends and enjoying this beautiful place he calls home. When he is not at work, he loves spending time with his growing family (he just welcomed his third grandchild this year!). Leo also enjoys kayaking, bicycling, hiking, photography, and riding his motorcycle.

To contact directly, please email leo-michael@leavitt.com

“Leo has been there for me every call I’ve made…he’s researched…found the answers…I feel very secure with his knowledge and abilities.  A very good man!  I’m fortunate to have him as my very capable agent.” – Irene S. | Read More

beckyBecky Greenway

Licensed Agent: Property & Casualty – Commercial




Becky is a sixth-generation San Juan Islander, born and raised. She has a strong background in business, having successfully owned and operated several of them prior to joining Safe Harbor in 2004. She’s not all business, though – she loves spending time with her husband, Mike, their two kids, and their two awesome dogs, Georgia and Jack. Becky is also a big fan of boating, fishing, and hiking. On the weekends, you might even catch her cheering on the Seahawks or enjoying a bonfire with friends!

To contact directly, please email becky-greenway@leavitt.com

Becky has been absolutely GREAT for me for almost 10 years! …EVERY question, EVERY situation handled quickly and efficiently. Becky is a top notch representative and “face” of Safe Harbor…” – Jerry H. | Read More

juan-and-ariesJuan UnpingcoJuan Unpingco

Licensed Agent: Property & Casualty, Life & Health




Juan grew up all over, as his father served in the US Navy for over 20 years. He and his wife, Carrie, moved to San Juan Island in 2007. They are proud parents of two children: son Aries and daughter Athena (but their miniature Dachsund, Stretch, still thinks she’s the baby). In his free time, Juan enjoys being silly with his family, “getting down on” some Madden (the video game), playing Fantasy Football, and rooting for the Seahawks. He has a weakness for sports jerseys, shoes, and pens. He’s also our office king of bad jokes.

To contact directly, please email juan-unpingco@leavitt.com

“Juan has provided outstanding service, he is prompt, courteous and pleasant. His knowledge and eagerness to serve are clearly evident in his work performance!” – Tim O. | Read More


Tanasha Webb

Licensed Agent: Property & Casualty, Life & Health




Tanasha spent most of her childhood moving from state to state with her family, following her father as he traveled for work. Hitting seven schools before age 12, her family finally settled down in Kooskia, Idaho, where she finished high school. Immediately after graduating, Tanasha visited the island and fell in love with it. She has now been an islander for seven years. When she’s not at work, she enjoys spending time with friends, lounging at the beach, fishing, hiking, gardening, and any opportunity she gets to be outdoors with her black lab, Whitt. She has become a Seahawks fan (not the bandwagon kind) and a growing community volunteer. She is very familiar with “small town livin’” and loves this island life.

To contact directly, please email tanasha-webb@leavitt.com

“Your service was outstanding. Tanasha Webb was totally responsive and ahead of all issues. We had trouble from our former insurance company to get our Center island property insured because it isn’t served by a public ferry. Tanasha went to work and got a wonderful policy for us right away. You are lucky to have such a wonderful employee. We plan to do business together for many years to come!” – Connie P. | Read More

Caitlin Greenway

Licensed Agent: Property & Casualty




Caitlin is newly licensed and is eager to get to know the ins and outs of the insurance world. She is a 7th generation islander, born and raised. Caitlin is a huge animal lover and loves spending time outside with her dogs, Piper and Izzy. In the summer, she loves getting together with family and friends and spending time at their family pond swimming and having BBQ’s. And of course, in the winter you will find her on Sundays cheering on the Seahawks. She and her boyfriend have recently started building their dream home in Foxhall as part of the Homes for Islanders program. They also just recently found out they are expecting their first child together!!

To contact directly, please email caitlin-greenway@leavitt.com

Samantha MichaelSamantha

Marketing & Events Manager, Bookkeeper




Sammi spent most of her childhood in Friday Harbor and is proud of her island roots. She graduated from Pacific Lutheran University with a BA in Anthropology, worked four years in the medical field, and then ended up coming back to the family business. She and her fiance live in Mount Vernon, and she commutes to the office weekly. When she’s not at work, she’s usually loitering at the gym, hiking with her pup Harlowe, or relaxing with a pint of local craft beer. She totally digs the Seahawks, Asian food, and true crime.

To contact directly, please email samantha-michael@leavitt.com


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