About Woodpecker Insurance

The Woodpecker Name — What’s Up With That?

Let’s be honest: turning 65 and figuring out Medicare isn’t exactly at the top of anyone’s list of fun things to do.
So, we asked ourselves: what if there were a way to make the experience a little more enjoyable? A little less intimidating? Maybe even bring a smile or two along the way? That’s where the woodpecker comes in.

Here in New Hampshire, woodpeckers are part of everyday life. Most people have spotted one in their backyard—or have a story about one hammering away on a tree, a house, or sometimes something it definitely shouldn’t be pecking.

Meet Woodrow Pecker, our Medicare mascot.

Woodrow is cheeky, witty, a little sarcastic, and never misses an opportunity to crack a joke about retirement, Medicare, or getting older. His favorite target is Rocky, our beloved Australian Shepherd, who takes the teasing surprisingly well.

But beneath the humor is a serious purpose. Medicare can be confusing. The choices can feel overwhelming, and the stakes are important. Woodrow helps remind us that while Medicare is serious business, the process doesn’t have to be stressful every step of the way.

At Woodpecker Insurance, we’re here to provide clear guidance, local expertise, and a little personality along the journey. If Woodrow can make you chuckle while helping you navigate Medicare, then he’s done his job.

Introducing

Larissa Troy

What do I love most about my work? The relationships. Our clients come to us not only because Medicare is daunting, but also because they want to have someone they personally know and trust standing side-by-side with them as they enroll in and manage their health insurance. I love onboarding our clients to coverage they understand and coverage that brings overwhelming value. And after they are enrolled, I love being there for them- for the quick calls just to check in on a Medicare detail, or the more complex calls of how Medicare and Medical health plans will operate in more serious situations. Simply put, Medicare and health insurance are constantly evolving. I like being the steady-eddy rock they can count on.

NH Licensed Insurance Agent #21381136

Introducing

Larissa Troy

What do I love most about my work? The relationships. Our clients come to us not only because Medicare is daunting, but also because they want to have someone they personally know and trust standing side-by-side with them as they enroll in and manage their health insurance. I love onboarding our clients to coverage they understand and coverage that brings overwhelming value. And after they are enrolled, I love being there for them- for the quick calls just to check in on a Medicare detail, or the more complex calls of how Medicare and Medical health plans will operate in more serious situations. Simply put, Medicare and health insurance are constantly evolving. I like being the steady-eddy rock they can count on.

NH Licensed Insurance Agent #21381136

Introducing

Christian Troy

What do I love most about my work? Well, really two things. First, the clients. Through our firm, I have had the great fortune to meet the most wonderful people, all with rich stories, deep knowledge, and with wonderful outlooks on life. Our clients are inspiring and as my own life moves on, they give me both inspiration and motivation for what is down the road for me and my own family. And secondly, I deeply enjoy getting to know my clients and ‘solving’ their health insurance coverage puzzle. Every client is different in their own way, and I enjoy the custom coverage architecture that we do to make sure each client is compliant, fully covered, and has their coverage optimized the way they want; and that they understand it! NH Licensed Insurance Agent #21379781

NH Licensed Insurance Agent #21379781

Um, not a woodpecker…

Rocky Troy

Our sometimes office dog

…but he wants to be a woodpecker. What he is, though, is an endless source of distraction to Mom, Dad, and our clients. Rocky is an Aussie Shepherd with the heart of a woodpecker, always caring and concerned for those in his forest.

How We Help

We’re independent, licensed Medicare agents who represent multiple insurance companies. That means our recommendations are based on what’s best for you—not any one carrier.

Whether you’re considering a Medicare Supplement (Medigap) plan or a Medicare Advantage plan, we’ll help you understand your options and choose the coverage that fits your needs.

And our relationship doesn’t end when you enroll. We’re here year-round to answer questions, help solve problems, and keep you informed when plans or benefits change.

How We’re Paid

Our services don’t cost you anything extra.
Insurance companies pay us a commission when we help someone enroll in a plan. That commission is already built into the cost of the plan, so you pay the same premium whether you work with us or enroll directly with the carrier.

The difference? With us, you get personalized guidance, ongoing support, and a local advocate at no additional cost.

Licensed, Trained, and Certified

Medicare is complicated, and helping people navigate it requires ongoing training and certification.

We maintain all required state licenses, complete annual Medicare and carrier certifications, and stay current with changing Medicare rules and regulations. Simply put, we’re trained to help you make informed decisions with confidence.

Local, Accessible, and Here for You

Our office is right here in Concord, New Hampshire. We’re not a call center hundreds of miles away—we’re your neighbors.

Like a good woodpecker, we’re never far away when you need us. From our nest to yours, we’re here to make Medicare a little easier, a little clearer, and a lot more personal.

Our office at Farrington House on Main Street, Concord, NH

Farrington House (Concord, NH)

Built in 1844, the Farrington House stands as a testament to the Greek Revival style that swept through America after the War of 1812.​ Designed as a duplex for two brothers, Samuel and Philip Farrington, it reflects a national trend towards Greco-Roman influences, a rejection of British styles after the War of 1812. The house, with its single entrance leading to twin staircases and parlors, was part of the expanding southern end of Concord. The brothers, successful merchants, sold it in 1866 to Joseph S. Lund, a farmer and entrepreneur. The Greek Revival, rooted in European Neoclassicism, became America’s “National Style,” embodying the nation’s ideals of democracy and republicanism.

Woodpecker Insurance

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