FORWARD DEPLOYED ENGINEER, OPERATIONS
Operations · Full-time
Seattle, WA, USA · Remote
Posted on Aug 28, 2026
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 management, bookable by the hour or in a weekly cadence, backed by a bench of vetted Pros who learn your family’s rhythms. 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
This role has the opportunity to define & create an entirely new role. Much like GTM engineers own & build GTM tooling and FDEs manage & build for their customers, 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 before a family or Pro ever feels them. Today its 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. You'll be close enough to the day-to-day to know exactly where the friction is, and technical enough to go build the thing that removes it. You're not handing requirements to someone else, you're shipping the automation yourself. Over time you lead this whole function as the product leader for Rosie's operations: the person who decides what "autonomous operations" means here and builds the roadmap to get there.
Our north star is 100% AI-managed matching and scheduling with a small, deliberate human-in-the-loop to keep all touch points “human first”. You will make this happen.
Who You Are
Operator and engineer in one: You've run real operations and you can write the code. You'd rather build the tool than file the ticket, and you're happiest closing the loop between "here's the problem on the ground" and "here's the system that fixes it."
AI-forward: You build with agents, LLMs, and automation as a default, not a novelty. You know how to turn a fuzzy human workflow into something a model can run reliably, and where a person can jump in when needed.
Data-minded: You don't ship automation on vibes. You build the evals, guardrails, and monitoring that tell you when a system is trustworthy and when it isn't, and make it self-improving.
Systems thinker: You see the whole operation as one system, can confidently organize and categorize consistent problems from one-off issues, find the real bottlenecks, and fix the root cause AND the symptom. You automate the toil and design out the failure modes.
Bias to action: You move fast, ship, measure, and iterate. You make confident calls with partial data and create clarity for the people around you instead of waiting for it.
Founder mode: You are the owner, and the buck stops with you. You treat the operations like your business inside the company and take full ownership of the metrics, successes, failures and growth.
What You'll Do
Run day-to-day operations: Own the operational engine: customer communications, matching, scheduling, coverage planning, and the daily save-the-day work. Keep it reliable while you re-engineer it underneath.
Build the autonomous stack: Design and ship the agents, admin tooling, internal dashboards, and workflows that take operations from human-run to AI-managed.
Consistent improvement: Stand up the evaluation, monitoring, and guardrails that decide when automation can run and when to bring humans in the loop. Measure quality, catch regressions, and keep raising the bar on what runs unattended.
Instrument everything: Define and build the metrics and visibility that show how the operation is actually performing — match quality, fill rate, time-to-match, reliability — and use them to decide what to automate next.
Multi-locale support: Build the operational playbook and tooling that lets Rosie launch a new city and run it lean from day one.
Lead the function: Set the vision for autonomous operations, own the roadmap, and grow the team and tooling as Rosie scales. You are the product leader for how Rosie runs.
Basic Qualifications
3+ years across operations and engineering, with real hands-on time in both — you've run complex operations and you've shipped production-grade software.
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.
Very comfortable in the unknown and always unblocking yourself relentlessly.
Ability to represent Rosie the brand to Pros & families alike via written and voice communication
Ability to work from Seattle on a hybrid basis, or remotely with travel at least once a quarter.
Preferred Qualifications
Prior 0→1, founding, or early-operator experience. Ex-founders and to-be-founders very welcome.
Experience with marketplaces, logistics, on-demand, or care and parenting products.
Experience building agentic systems, evals, or human-in-the-loop automation in production.
Fluency with modern AI tooling across research, prototyping, and building — always ahead of the curve on the best tools to work with.
Why Join Now
Impact: You'll decide what "autonomous operations" means at Rosie at the exact moment those systems are built for the first time.
Timing: Early enough to own the entire function and the stack that runs it.
Ownership: Salary plus founding equity, with expectation to grow with the company.
Mission: You'll build the systems that power modern family life. There's no bigger problem worth solving.
Compensation
Competitive salary plus founding equity, commensurate with a founding leadership seat.