Forward Deployed Engineer, Operations

About Rosie

Rosie is reimagining care, for families & for caregivers. We created a new category of care: flexible, on-demand childcare and household management, bookable by the hour or in a weekly cadence, backed by a bench of vetted Pros who learn your family's rhythms.

The Role

This role has the opportunity to define & create an entirely new function. Much like GTM engineers own & build GTM tooling, the Founding Operations Engineer will fully own the day-to-day operations at Rosie (the lifeline of the business). Not only will you manage the daily operations and program development, your primary goal is to build the AI automations that will do the work.

Today, a lot of what makes Rosie feel magical happens behind the scenes: matching a family to the right Pro in minutes, filling a last-minute cancellation, onboarding and vetting new Pros, keeping schedules tight, and catching the edge cases. Today it's a mix of agents, humans and software tooling. Your job is to run it well and build the systems — agents, admin tooling, evals, dashboards — that make it run itself.

This is a rare hybrid seat: half operator, half engineer, full product owner. Our north star is 100% AI-managed matching and scheduling with a small, deliberate human-in-the-loop.

## Who You Are

• Operator and engineer in one: You've run real operations and you can write the code.
• AI-forward: You build with agents, LLMs, and automation as a default.
• Data-minded: You build the evals, guardrails, and monitoring that tell you when a system is trustworthy.
• Systems thinker: You see the whole operation as one system and fix the root cause AND the symptom.
• Bias to action: You move fast, ship, measure, and iterate.
• Founder mode: You are the owner, and the buck stops with you.

## What You'll Do

• Run day-to-day operations: customer communications, matching, scheduling, coverage planning.
• Build the autonomous stack: agents, admin tooling, internal dashboards, workflows.
• Stand up evaluation, monitoring, and guardrails for automation.
• Instrument everything: match quality, fill rate, time-to-match, reliability.
• Build the operational playbook for new city launches.
• Lead the function and grow the team.

## Basic Qualifications

• 3+ years across operations and engineering, with real hands-on time in both.
• Strong software engineering fundamentals — you can build and ship internal tools, integrations, and automations end to end.
• Direct experience building with LLMs / AI agents in a production setting.
• Data obsessed — you instrument, measure, and make decisions from what you see.
• Ability to work from Seattle on a hybrid basis, or remotely with travel at least once a quarter.

Compensation

Competitive salary plus founding equity, commensurate with a founding leadership seat.

Apply on the career site