Co-Founder Hiring Assignment · Gitwit Venture Studio Stedmon Harper · September 2026

Why most people don’t switch insurance — even when they shop.

Five pages, and you only need the first. The brief is the deliverable — it stands on its own. The walkthrough is the short version I would talk from in the room.

The assignment I was given

Harbor is a new insurer selling car and home coverage. It cannot outspend the big companies on advertising and nobody has heard of it. Lots of people shop for insurance. Far fewer actually switch. That gap has been there for decades.

Go and learn from real behavior. Find one non-obvious reason it happens. Propose one thing Harbor could do about it — and be clear about what you are giving up by choosing that one thing.

Harbor is not a real company. It is the imaginary insurer this work was written for. Everything behind these pages is real — real insurance websites, real documents, real people, real accounts. Four conversations, two live accounts, three websites and one paper bill, over one day.

The site I sent with my original application →