Meet the family

The people behind your policy

We're a small, family-run agency — and that's exactly the point. When you call, you talk to us. When you have a claim, we're in your corner.

Margaret Calloway

Margaret Calloway

Principal Agent & Founder

Margaret grew up in Fairbanks, the daughter of a Lutheran pastor and a school principal. She spent her early career volunteering with food banks and youth programs before earning her insurance license in 1999. She founded Northern Advantage because she saw how underserved Alaska's non-profits and faith communities were — and decided to do something about it. Twenty-five years later, she still personally reviews every new policy.

Alaska roots3rd generation Alaskan. Fairbanks born, Anchorage based.
Fun factRuns the Iditarod Trail Invitational 350 every February.
Robert Calloway

Robert Calloway

Senior Agent

Robert spent twelve years as executive director of a mid-sized Anchorage non-profit before joining Margaret at the agency. He knows the world of non-profit governance, grant compliance, and board liability from the inside — which makes him uniquely qualified to explain why D&O coverage matters and what it actually protects. He joined the agency in 2011 and has never looked back.

Alaska rootsMoved to Alaska in 1998. Never left.
Fun factFormer competitive dog musher. Now just a recreational one.
Dana Whitfield

Dana Whitfield

Client Relations & Quoting

Dana is the first voice most clients hear, and she makes sure that first impression counts. Born and raised in Anchorage, she joined the agency after a decade in non-profit administration. She handles quoting, renewals, certificates of insurance, and the hundred small questions that come up between policy dates. She's known for calling clients back the same day — every time.

Alaska rootsAnchorage born and raised. Wouldn't have it any other way.
Fun factVolunteers every summer with a Kenai Peninsula salmon habitat restoration crew.

How we work

What makes us different

You talk to us, not a call center

Every client has a direct line to the person who wrote their policy. No ticket numbers, no hold queues, no transfers.

We know your world

Our team has worked inside non-profits and faith communities. We understand your budget pressures, your board dynamics, and your mission.

Alaska-specific expertise

We write policies for Alaska's climate, Alaska's regulations, and Alaska's unique community landscape — not a generic national template.

No surprises at renewal

We review every policy before renewal and call you if anything needs to change. You'll never open a renewal bill and wonder what happened.

Ready to work with people who know your name?