Our Team

Robert Woodman, Independent Insurance Agent, Owner

Robert Woodman
Independent Health Insurance Agent

Rob Woodman started working in Financial Services in 2015 shortly after retiring from his 20-year career as a Great Lakes Merchant Marine Pilot. He acquired his Life & Health Insurance License in that year and his Series 65 Securities License shortly thereafter. In 2018 Rob shifted his focus to Medicare and acquired his AHIP Certification and became registered with Aetna, Anthem/Maine Health, Humana, Martin’s Point, United Healthcare (AARP) and WellCare. Starting in 2023, his daughter Hilary joined him in the business.

Rob is an active member of Saint Peter’s Parish in Portland where he Lectors and sings in the Choir. He lives in Westbrook with his little dog Begonia.


Hilary Mansfield, Independent Insurance Agent, Owner

Hilary Mansfield
Independent Health Insurance Agent

Hilary Mansfield is a state licensed, independent Medicare insurance agent. She recently joined the family business and feels grateful for the opportunity to learn the ropes from her father, Robert Woodman. A lifelong learner with a degree in education and over thirteen years of experience in the publishing industry, Hilary brings a wealth of knowledge and expertise to the Woodman Mansfield Company.

In her publishing career, Hilary specialized in project management and process improvement, as well as graphic design and marketing. She enjoyed collaborating with other creative professionals in the news, calendar, book, and web publishing fields.

Hilary is very happy to use her positive attitude, creativity, and passion for education to assist people in navigating the confusing system of Medicare insurance.

When she’s not taking nature photos or at the office or whipping up the latest logo, website, or business card, she enjoys spending time with her horse, Louie, and swimming or kayaking.


And because we understand that when you’re nearing retirement age you may need services beyond Medicare insurance, we have teamed up with trusted professionals to provide the guidance you may need.

Give us a call or send us an email and we’ll be happy to connect you. We’re here to help!

  • Social Security Income Planning

  • Financial Planning

  • Estate Planning

  • Real Estate downsizing and transfers

  • Elder services