Seattle or Remote with travel • Full-Time • Salary + Competitive Equity

About Rosie

Rosie is reimagining care, for families & for caregivers.

We created a new category of care: flexible, on-demand childcare and household support, bookable by the hour, backed by a bench of vetted and professionally trained Pros who know your family. Families finally have a way to get the help they actually need with minimal effort.

We're building the infrastructure that powers modern family life: a world where parents book care the way they text a friend, where caregivers build real careers doing work they're proud of, and where having support at home just feels normal. We're expanding to new cities, and we're just getting started.

The Role

As Rosie's Head of Engineering, you'll work directly with the founders to set the technical north star — the architecture, infrastructure, and engineering philosophy that determines not just what we can build today, but what we'll be capable of building two years from now.

You think in systems. You know the difference between technical decisions that compound over time and ones that quietly accumulate debt. You make the former, and you catch the latter before anyone else does. Rosie is at the inflection point where the decisions made in the next 12 months will define the ceiling of the company — you'll be the person who sets that ceiling as high as possible, building the infrastructure that lets a small, exceptional team move with the leverage of one ten times its size.

You'll spend most of your time looking up and ahead, partnering with the founders on product strategy, anticipating where the business is going, and making sure the technical foundation is already there when we arrive.

Who You Are

• Systems thinker: You see the architecture & user need behind the feature request. You make decisions that compound positively over time and spot the ones that don't before they become expensive.
• North star setter: You build the roadmap. You have a strong point of view on where the product and infrastructure need to go and the conviction to drive the team there.
• Founder-minded: You operate with the same urgency, ownership, and long-range thinking as the people you're building alongside. You are co-authoring the vision.
• Multiplier: You build systems, culture, and infrastructure that make everyone around you faster and more effective. The team you hire and the foundation you lay will define Rosie's engineering capacity for years.
• Technically excellent: You have deep, earned opinions on architecture, reliability, and scale — and you can get into the weeds when it matters.
• Calm in complexity: You thrive in ambiguity, make decisions with incomplete information, and never confuse motion with progress.

What You'll Do

• Set the technical direction: Own Rosie's engineering roadmap and architecture. Make the foundational decisions on infrastructure, tooling, and systems design that the company will build on for years.
• Partner with the founders: Sit at the table on product strategy, business direction, and company building. Engineering at Rosie is a co-equal input into the business.