Principal Software Engineer

About the Role

We are hiring one principal engineer, and we are hiring them to raise the ceiling of what this team can build.

Engineering is six people today and will be fourteen inside a year. Our surface area is far larger than that: reservations, payments and money movement, dock and slip management, rent roll, boater CRM, service and work orders, accounting integrations, a native iOS app, and now multi-currency for international markets. That math only works if we get dramatically better at building, not just bigger.

You will rebuild how we build. We treat AI as core development infrastructure, not a side experiment. We want someone who pushes the automation of our development lifecycle much further than it is today, proves it on real production work, and pulls the rest of the team up to that bar.

You will own the architecture that makes speed safe. We are twelve years into a system carrying real traffic and real money. Going faster only works if the foundation holds while we stack international, enterprise, and new verticals on top of it. You make those structural calls.

We are not hiring a principal to be the best coder in the room. We are hiring one so that in eighteen months a team of fourteen ships like a team of forty.

Who Thrives Here

The people who thrive at Dockwa have usually founded something, or joined something early and grew with it. They think in outcomes rather than tickets. They have opinions about the product and the business, not only the code. They would rather ship something a marina operator notices on a Saturday morning than win an argument about abstractions.

You should want to steer. There is more consequential work here than there are people to do it, which means you will decide what gets built at least as often as you build it.

What You Need

Production software you owned outright, end to end, including after it shipped.

• Real AI fluency with receipts.
• Not tool familiarity.
• Work you could not have delivered without it.

• Comfort across a full stack. Ours is Rails, React, Postgres, AWS and Swift, but we will take judgment over stack match every time.
• Architectural decisions you had to live with afterwards, in systems you did not originally write.
• Evidence you changed how a team worked, not only what it shipped.

How We Hire

Short, collaborative, and built around real problems rather than memory tests or puzzles. We are screening for motivation and judgment over trivia, and we want you to finish the process more excited than you started it.

How We Work

We are a small team that is winning. Problems grow exponentially with each person added, not linearly, so we keep the organization lean on purpose and put people at the source of problems with real ownership.

• We automate before we hire.
• We ship quality at speed and treat those as compatible.
• We own the full loop from discovery to payment to analytics, because controlling the data is what makes the intelligence products possible.

We move fast, and context does not always land perfectly. It is always fine to ask why.

• We have an institutional partner in PSG and an annual plan that’s in our control.
• We’re investing heavily in product and engineering because the operating system of the marine economy is ours to build and own.
• Acquisitions are part of how we grow, and we have dedicated budget behind that as well.