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.
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.
What’s so important about this role
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.
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.
Who You Are
You've shipped work you're proud of, and you know the difference between work that's good and work that just looks good. What we care about most is how you think about the problem we're solving. Holly makes real decisions that affect real people. She might reassign a nurse's shift at 2am. Someone has to look at that decision and trust it, and you'll be the person who decides how that trust gets built. Your design decisions won't move a metric on a dashboard. They'll affect whether a unit is safely staffed. That's not a problem you can solve with established patterns or a well-scoped brief. You'll need strong opinions, the ability to work through ambiguity, and the conviction to defend what you ship.
This is a place where design leads, not where it's just valued. If you need the problem fully defined before you start thinking, or you treat Figma as the finish line, this isn't the right role.
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]
20-minute phone screen with our chief of staff
30-minute in-person interview with our engineering lead
Design challenge (take-home, approx. 2 hrs of est work time)
1 hr interview with our CEO, co-founder AK
Other details
Compensation & Benefits
Salary
$130,000 – $145,000
Equity
0.5%
PTO
15 days
Healthcare
75% covered by the company
Location
In-office, Jackson Square, San Francisco (5–6 days/week)
No recruiters, no-part timers, no remote – thanks.
2-3 yrs exp. Working in a VC-backed startup environment highly desired
