Passion. Place. Progress.

Three years ago, we had 21 people. Today, 50+. The infrastructure of Windsor is being built in real time, by the people inside it. If you want to grow with something, this is the moment. We're not just filling roles. We're creating a legacy.

We hire people that don't need a map. But are bold enough to create it. And willing to blaze the trail. We are incredibly intentional on who we hire. And that is by design. When you join Windsor, you will join a team worth being a part of.

We take the best idea in the room. Full stop. We don't care where it comes from or who's holding it. Good ideas don't need a ladder here. We move fast, stay flat, and cut the approval layers that slow most companies down. If you have something worth saying, say it. If it's the best idea in the room, it wins.

At Windsor, we have no KPIs. Great teams aren't built on metrics. They're built on people who consistently deliver for each other.

We don't limit our hiring to a ten-mile radius. We hire the best talent—wherever they are. By being a remote first company, our only limitation to the best is simply a WiFi connection. Our team spans across state lines and globally.

Building a team that performs at a high level over the long run requires more than good hiring. It requires taking care of the people you bring in. That's why we invest in a benefits package designed to support you — not just at work, but in life.
Our comprehensive coverage includes Medical, Vision, Dental, Disability, Life Insurance, and 401(k). Medical benefits come paired with an HRA card, FSA-Traditional, and FSA-Dependent plan options — plus access to tools like Headspace and discounts through ClassPass, because wellness extends beyond the clinic.

Great work requires great rest. In your first year, you'll have 31 guaranteed days off total - 15 vacation days, 5 sick days, and all federal holidays. In your second year, this steps up to 36 guaranteed days, as you will have 20 vacation days. This does not include Windsor Days, which are days we close the office early. For example, a half day on the day before Thanksgiving, a half day on Christmas Eve, etc. However, Windsor Days are not guaranteed to be offered on an annual basis. The offering of Windsor Days depends on the needs of the business!