Principal Software Engineer

Dockwa

About The Position

We are hiring one principal engineer 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.

Requirements

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.

Nice To Haves

Founded something, or joined something early and grew with it.
Think in outcomes rather than tickets.
Have opinions about the product and the business, not only the code.
Would rather ship something a marina operator notices on a Saturday morning than win an argument about abstractions.
Want to steer.
Decide what gets built at least as often as you build it.

Responsibilities

Rebuild how we build.
Push the automation of our development lifecycle much further than it is today.
Prove AI integration on real production work.
Pull the rest of the team up to a higher bar of development automation.
Own the architecture that makes speed safe.
Make structural calls for system foundation to support international, enterprise, and new verticals.
Enable a team of fourteen to ship like a team of forty in eighteen months.