Head of Design for AI Operating System in Healthcare

ShiftOS is the AI lab building Holly, your healthcare org's new favorite hire. Holly is an AI healthcare admin that handles staff schedules, call-offs, PTO requests, license tracking, and compliance monitoring autonomously. She trains on your org's unique needs, never sleeps, and never forgets. She's able to grow and scale with orgs from 25-2000+ employees; handling the manual work of managing every logistic that goes into ensuring your clinical staff is exactly where they need to be and when, with 100% compliance.

The Problem

Every healthcare operation in the country runs on the same thing: thousands of people showing up to the right place at the right time. The software that manages all of that is, almost without exception, terrible. It costs health systems millions, burns out the people it's supposed to help, and hasn't meaningfully changed in decades.

We're building the thing that replaces it. ShiftOS is an AI operating system for healthcare operations, powered by Holly, our AI agent. She handles scheduling, compliance, credentialing, workforce management, all of it. She gets to know your team better than most new hires, gets sharper the longer she works, and she's got the personality to match. She's a teammate, not just software. Nobody else in healthcare is building AI like this, and that's why we're going to win.

Why This Role Matters

Design is the reason our product feels different from everything else in this space. We need someone to own it. Our team values having a product in the healthcare market that's beautiful to interact with; a key differentiator for us vs. other healthcare SAAS platforms. It's agentic first, always. And success is being measured by how little time admins spend on the dashboard.

You'll own the entire design surface: product, interaction, everything the user touches. No handoffs, no waiting on anyone. You'll get a problem and the space to figure out the right way to solve it. Your job is to build a vision and make the team see it so we can ship it together.

You're early enough to define everything. The design vision. The system. How the team grows. The patterns we use and the ones we throw out. This isn't joining something already in motion. You're setting the direction. The person that succeeds in this role defines how industries operate in the future.

The Work

You'll work directly with engineering and product. Not handing off specs, building alongside them. The team is experienced, fast, and opinionated. People will push back when something doesn't feel right, and they'll expect you to do the same. The people here will make you better, and they're actually fun to be around while they do it.

The design problems don't have solved patterns. How do you make an AI agent that fills ICU shifts feel trustworthy? How do you give a charge nurse real control over Holly's decisions without slowing everything down? How do you show why the system made a choice, not just what it chose? If these questions excite you, this is your role.

We are seed stage, we've raised $6.8M and are live with users: clinicians, doctors, pharmacists, etc.. Things move fast, the job isn't fully defined, and honestly that's the whole appeal. The designer we hire now will shape this company as much as any engineer or founder.

What You Will Own

What you'll own is the product roadmap, coordinating with our eng / CS / and marketing teams, the shape of Holly's future features, and founding team equity.

This is not a role for people who want to cruise (unfortunately, healthcare is broken and we're up against a clock).

It's in person, 5-6 days a week at our office in Jackson Square.

Who Should Apply

If you're thinking this sounds bad, and like it's going to be a hard job with a lot of grunt work and figuring it out — you are correct. Most people should not apply.

However, if you want to take a moonshot on something extremely complex and test your patience, skills, and ability to execute; we should chat! Apply here or send us an email ashley@shiftrx.io

Don't send a resume, just your LI, and some reasons on why you think you should own the Holly product.

Ideally, you're smart af, you've worked on healthcare scheduling / compliance / etc. before, product before at a startup (desired but not necessary if you're a fast learner), you're good with owning things end to end, and a lot of ambiguity.

No recruiters, pls.

Compensation

• Base salary: $200K–$400K
• Equity: 1–3% ownership
• Full benefits + relocation support if needed

This is a rare opportunity to build the technical foundation of a generational company. If you're interested, please apply or send an email to ashley at shiftrx dot io with the subject: head of eng at shift.

How to Apply

Send us two pieces of work: the one you're most proud of and the one you learned the most from. Tell us what you think is wrong with how AI products are being designed right now. Be specific. We read every application.

Application Process (we move quickly, and like to run our process in approx. 1 week)

1. 20-minute phone screen with our chief of staff
2. 30-minute in-person interview with our engineering lead
3. Design challenge (take-home, approx. 2 hrs of est work time)
4. 1 hr interview with our CEO, co-founder AK