Head of Engineering | Full-time
Rosie
Posted on May 4, 2026
Head of Engineering
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.
Build for scale: Design the systems and infrastructure that let a small team operate with massive leverage & get your hands dirty as a builder yourself. You will be writing code.
Hire and develop the team: Define what great engineering looks like. Set a high bar, recruit to it, and build a culture of craft, accountability, and speed.
Maintain technical excellence: Establish engineering best practices, documentation, and standards. Keep the codebase healthy as we move fast.
Stay ahead: Anticipate where the business is going and make sure the technical foundation is ready when we get there. Establish an AI-first culture that magnifies the team’s impact & always keeps us on top of the latest functionality.
Basic Qualifications
5+ years of professional engineering experience, with meaningful time in senior or staff-level roles.
Proven track record of setting technical direction — architecture decisions, infrastructure choices, and engineering culture at a company level.
Deep experience with full-stack systems and production-grade infrastructure at scale.
Strong command of modern AI/ML tooling and experience building products with LLMs at the core.
Experience with React/Next.js, TypeScript, Postgres, AWS, OpenAI / Anthropic.
Demonstrated ability to hire and develop engineers.
Ability to work full-time, on-site/hybrid in Seattle, WA. If remote, you're able to travel at least once per quarter.
Preferred Qualifications
Prior Founder, founding engineer or CTO at a start-up experience — built from 0→1.
Experience building consumer marketplace or two-sided platform products.
Background working on AI-native products, including self-hosting, fine-tuning, and running evals.
Experience with mobile development (iOS or cross-platform).
Deep knowledge of security best practices in consumer applications handling sensitive family data.
Why Join Now
Impact: The technical decisions you make in the next 12 months will define the ceiling of what Rosie can become.
Timing: Early enough to set the culture, the bar, and the direction.
Ownership: Salary + meaningful equity, with true co-builder responsibility.
Mission: You're building the infrastructure that powers family life. There is no greater mission than this.
Compensation
Your success is our success. Competitive salary with significant equity.
To apply, email hi@rosiematch.com with: a link to a system or product you've architected that you're proud of, how you think about the relationship between engineering and product strategy, and a few sentences on why this mission calls to you.