Software Engineer, ShiftOS

Location: San Francisco | Stage: Seed ($6.8M raised) | Equity: 0.25 to 0.75% ownership

The problem and the product

Shift-based workforces run the world. Hospitals, restaurants, clinics, anywhere that lives and dies by who shows up and when. The software managing all of that is an embarrassment. We're talking spreadsheets, group texts, fax machines, and enterprise tools so bad that managers have given up on software entirely and are just doing it from memory.

We're burning it down.

ShiftOS is an AI-native workforce coordination platform built for organizations that can't afford to get staffing wrong. The core of it is Holly, an AI worker to generate schedules and automate the manual orchestration that goes into running a workforce.

Call-off at 6am? Holly finds coverage, reaches out, confirms the swap, updates the schedule. The manager finds out after it's already handled. She tracks licenses, keeps people compliant, updates payroll — all the boring shit that bogs people down from their actual jobs.

We didn't raise money and go looking for a problem. We built ShiftRx first: 1,000+ pharmacies, 12,000+ clinicians, proved the model, and used that foundation to build ShiftOS and launch the Holly product. We’ve raised $6.8M for our seed round, we have real customers on both products, are deploying in enterprise environments; we’re onboarding one enterprise customer a month right now. We’re looking to hire to go faster, because we have the demand.

We're in SF, with a sick spot in Jackson Square. We need engineers who want to own something. Real equity: 0.25 to 0.75%. Direct line to the founders. Architecture decisions that ship immediately. If you want a job, this isn't it. If you want to build something meaningful at the early stages of a generational company, come talk to us.

Who you are building with

Our engineering team is small, mighty, and honestly a little unhinged in the best way possible. We take the work incredibly seriously, but we do not take ourselves seriously at all.

On any given day, you will find us deep in the trenches debugging a complex agentic workflow, and ten minutes later, someone is dropping a cursed, AI-generated image of the CEO into Slack. We play around, we roast each other, and we laugh a lot. But when it is time to ship, we lock in and deliver.

Because we are a small group, we rely heavily on each other. We have a ton of experience across the team, and we are always here to offer guidance, pair program through a nasty bug, or just act as a sounding board for a weird architectural idea. You are never building alone here.

What your week looks like

No week looks the same here. You will be making Holly feel like a real coworker, building workflows that are seamless for our customers and ourselves, and rethinking how people interact with their devices to manage a workforce. You will touch the entire codebase.

Build and ship daily. One morning you might be tightening up a UI workflow so it actually feels good to use, and by the afternoon you are optimizing a backend service that Holly depends on. The next day, you are designing agentic workflows that let Holly handle a scheduling problem end to end like a teammate would. The surface area is wide, and the problems are genuinely interesting.

Own infrastructure decisions. You will design and evolve our cloud infrastructure (AWS, Terraform, CI/CD). You are not inheriting a pile of someone else's opinions. You are laying the foundation with us.

Make Holly smarter. Holly is not a chatbot bolted onto a dashboard. She is becoming a real coworker for ops teams. She learns an organization's rules, handles scheduling autonomously, tracks licenses before they lapse, and flags problems before humans even notice them. You will build the agentic systems and optimization layers that make that possible. If you have been wanting to work on AI that actually does things in the real world, this is it.

Talk to customers. You will hear directly from the people using what you build. Customer feedback shapes your priorities, not a game of telephone through three layers of PMs. This keeps the work grounded and honestly makes shipping feel way more rewarding.

How we operate

We are a small team that ships fast, but "fast" does not mean reckless. It means we trust each other to make good calls, cut scope intelligently, and skip process that does not earn its keep.

Autonomy with context. You will own your work end to end, from design through deploy. But you are never working in a vacuum. We think out loud together, challenge each other's ideas, and consistently make better decisions because of it.

Collaboration without theater. No stand-ups for the sake of stand-ups. No PRs sitting in review purgatory. We pair when it is useful, we async when it is not, and we optimize for momentum.

Speed with conviction. We ship daily. We talk to customers weekly. We are not afraid to throw away code that taught us something. If you have been stuck somewhere that takes six months and a committee to get anything out the door, this will feel like a different sport entirely.

Who you are

4 to 8 years building and scaling SaaS products. Whether it is startup or enterprise, we care about what you shipped, not where.
Full-stack fluency. Strong in React/Next.js/TypeScript on the frontend and TypeScript and Postgres on the backend. You do not need permission to jump between layers.
Infrastructure comfort. AWS, Terraform, Postgres, and containerization. You have operated in production, not just tutorials.
AI curiosity. You have built with LLMs, played with optimization libraries, or have a genuine itch to go deep. We will teach you the domain. Bring the engineering instinct.
Builder mentality. You thrive in ambiguity. When requirements are fuzzy, you dig into the use case with the team, clarify what matters, and start building. You do not wait for a perfect spec to show up.

Bonus points: Experience with scaling systems, security best practices, LLM engineering, memory and context management for AI agents, or building products in healthcare.

Compensation

Base Salary: $120-$165K

Equity: 0.25 - 0.75%

Benefits: Medical, Dental & Vision coverage. Company pays 75%

Unlimited PTO

This is early-stage equity with real upside. At our current trajectory, this is not a lottery ticket. It is a bet on a team that is already winning customers.

Why now, why us

Most "early engineer" roles are at companies still figuring out what to build. We already know. ShiftRx proved the wedge and is a profitable product line, Holly has customers since going to market in January, and we have the funding and the demand to go after this full speed. What we need is engineers who want to build something massive from the ground floor.

You will have the equity to benefit meaningfully, the visibility to grow into technical leadership as we scale, and the rare chance to build core infrastructure for an industry that has not been touched by good software in decades.

Workforce infrastructure is decades behind.

We are building the replacement. Come build it with us.