Come for the mission. Stay for the experience.

Let’s keep things simple: we’re a talented, hard-working, and compassionate team driving towards a mission that impacts every single one of us — even you.

HealthJoy is at the forefront of using AI and machine learning to transform the healthcare benefits industry. We’re building intelligent platforms that use predictive analytics, natural language processing, and machine learning to guide employees to affordable, high-quality care — consolidating health and wellness strategies into a simple, unified digital experience. This leads to healthier employees and a healthier bottom line.

HealthJoy has garnered workplace awards from Inc. 's Fastest Growing Startups and Built In Chicago’s Best Places to Work while growing globally to nearly 375 team members. We’re continuing down the path of high growth and high impact, and this role is a key member of the Product team making that happen.

Your Domain

You'll be the primary design architect for the external user side of HealthJoy: broker partners, HR administrators and employers, employees, and their families. Decisions made on the partner side shape how members engage with their benefits, and vice versa. You'll need to hold both in your head at once.

You'll work in both directions: responding to product and engineering needs, and bringing your own ideas forward. The best designers here do both — sharp execution partners when work is in flight, and intentional vision-setters who show the team what's possible three to six months out. Like every role here, you're not constrained to a predefined scope. If you see a problem worth solving, you make the case and go.

How This Role Works

Design has changed. This role operates across three layers simultaneously. You need to be strong in all three.

Execution — Real-Time Signal Shaping

You're embedded with engineers building fast. You're not just reviewing UI; you're tuning how outputs feel. Whether a response creates trust or anxiety, whether a flow adds cognitive load or removes it, whether an interaction confirms or breaks a user's mental model.

You give real-time judgment. You ship with the team, often directly in code. "This creates anxiety. Adjust it" or "this is good enough, ship it" — without a two-week cycle behind either call.

System Design — Human ↔ AI Interfaces

This is where the role is different from most design jobs. You're not just designing screens. You're designing the interface between people and AI behavior: what happens when an AI recommends something and the user isn't sure whether to trust it, how a member's prior context should shape what they see next, how to present a recommendation that's probabilistic rather than certain without losing the user's confidence.

At HealthJoy, this means things like: how should our AI assistant handle a benefits question it can't answer confidently? How do we design the broker-facing view of AI-generated member insights so that brokers act on them rather than ignore them? What does a good feedback loop look like when we want members to correct the system? How does the member’s experience get personalized across all interaction modalities, not just limited to conventional UI?

Direction — Coherence Over Time

AI-native systems can generate infinite features. Without direction, that turns into chaos. Your job is to define trajectories that keep the product coherent, making sure we're building a unified intelligence, not disconnected feature islands.

This isn't a two-year vision deck. It's fast prototypes, interaction experiments, something concrete the team can react to. You're steering how the product thinks over time, not just how it looks.

What You’ll Do

Real-Time Design Judgment. Be the quality signal for your product area. Evaluate what's being built, give fast and clear feedback, make calls in the moment. Know when something is ready and when it isn't — and say so with enough clarity that engineers trust you.

Design Inside the System. Work directly in code and AI workflows. Shape outputs through how they're structured and presented, not just through what they look like. Use AI tools to generate, test, and iterate fast.

AI Interaction Design. Design how users interact with agents and assistants that don't always give the same answer twice. Handle ambiguity, uncertainty, and evolving context. Make AI behavior legible and trustworthy to people who didn't build it.

Cognitive Load and Perception. Reduce friction in decision-making. Structure information to match how people actually think. Control how users interpret what the system is telling them. This is closer to behavioral design than traditional UI work.

Near-Term Vision Setting. Block time to look ahead. Build prototypes that define interaction patterns and give the team something real to align around. This isn’t a deck that explains the future, but something they can use and react to.

System Coherence. Make sure all surfaces feel like one product. Broker experience, member experience, AI assistant behavior should be aligned, not fragmented. You're responsible for the consistency of the intelligence, not just the visuals.

Field Signal Collection. Talk to users constantly, including brokers, members, and internal teams. Bring back insights that change how the team thinks, not just confirmation of what we already believe.

What We’re Looking For

Minimum of 5-7  years of product design experience. Healthcare background not required — we'll give you the domain context.

Judgment over process. You look at something and know quickly whether it's right and why. You can explain that clearly enough that engineers and PMs trust the call.

Systems thinking. You think in flows, states, and feedback loops rather than just components and pages. You see how a decision in the broker UI creates a downstream effect on a member's experience.

AI-native mindset. You use AI tools daily. More importantly: you've thought hard about designing for AI behavior — how to present outputs that aren't deterministic, how to build interfaces that adapt, how to create trust when the system is probabilistic. If you haven't done this professionally, show us what you've explored on your own. Side projects count.

Execution velocity. Real-time feedback, fast decisions, no over-processing. You keep teams moving rather than creating bottlenecks.

Comfort in code. You're willing to go there, to edit UI directly, tweak interactions, and ship quality rather than writing a spec and hoping. With AI tools, the barrier is lower than ever. Be genuinely excited to use them.

Cognitive empathy. You understand where people get stuck, what creates trust versus anxiety, and how to design for perception in addition to function.

A portfolio that shows both. We want to see how you respond to team needs and how you identify problems the team wasn't already looking at. Show us execution quality and directional thinking. AI or adaptive systems work is a plus. Side projects and experiments count.

What We’d Want to See in Your Portfolio or Design Brief

The standard portfolio review isn't quite enough for this role. Beyond execution quality and craft, we'd want to understand:

How you handle uncertainty in the interface. Show us a time you designed an experience where the system's output wasn't always predictable, consistent, or confident, and how you made that legible and trustworthy to the user. If you haven't done this professionally, describe how you'd approach it.

How you set direction, not just execute it. Walk us through a moment where you identified a problem the team wasn't focused on, framed it, and got people aligned. What was the artifact that made it real — prototype, demo, something else?

How you've worked at pace. Not a polished case study. We want to see the judgment calls. What did you decide to ship? What did you kill? How fast?

Your AI practice. What tools are you using, and what have you built or explored with them? What do you think about designing for AI behavior that most designers are getting wrong? We want your point of view.

System thinking across surfaces. Show us something where a decision you made in one place had downstream effects on another. How did you reason about the tradeoffs?

This Role Is Not For Everyone

If your best work comes from a structured design process with defined phases and clear handoffs, this role will be a difficult fit. If you’re most comfortable producing polished mocks and waiting for the next brief, look elsewhere. If working in code alongside engineers sounds like someone else’s job, this isn’t the right place.

If you read that and thought “good — that’s how design should work now,” keep going.

Reporting & Team

This role reports to the Director of Product. You’ll work closely with Product Managers, Engineers, and go-to-market teams, with direct support on cross-functional alignment and business context from senior teammates.

You’ll also have direct, unlimited access to executives — including the CPO. We operate an open calendar policy: if you need time with someone, add it.

Total Rewards

Job Level: Band 40

Base Compensation Range for Job Level: $145,000 - 175,000 annually

The cash compensation above includes base salary only. Certain roles are eligible for additional cash incentives such as commission, annual bonus targets, overtime pay or other variable incentives.

HealthJoy maintains a comprehensive strategy to determine rewarding and competitive packages for individual compensation for new hires, internal promotions and internal job changes. This strategy is based on several factors unique to each individual, including: 1) the skills, experience and qualifications of the individual; 2) the responsibilities and demands of the role; 3) analysis of external market data; and 4) company budget and financial performance.

HealthJoy is a remote-first employer. The disclosed range estimate has not been adjusted for the applicable geographic differential associated with the location at which the position may be filled.

At HealthJoy, it is not typical for an individual to be hired at or near the top of the range for their role, and compensation decisions are dependent on the facts and circumstances of each role and individual.

In addition to cash compensation, HealthJoy offers a rich “Total Rewards” package that includes:

• Medical, Dental, and Vision insurance packages
• HSA contribution match
• Stock options for eligible roles
• 401k match
• Paid parental leave
• Company sponsored Short Term and Long Term Disability coverage
• Flexible PTO

Commitment to Equal Pay

At HealthJoy, we are committed to creating a diverse and inclusive workplace where everyone has the opportunity to succeed and thrive.

We believe that everyone should be paid based on their qualifications, experience, and the work that they do, and not on their gender, race, or any other personal characteristic. Our compensation practices are essential to fostering a diverse and inclusive culture where we value the contributions of all our employees.

We conduct thorough annual reviews of employee pay and our pay practices to ensure we reward the right behaviors and are providing equal pay for equal work.

Additionally, we assess the external market and internal equity across like roles. As part of our regular review of pay practices, HealthJoy examines employee pay for potential disparities between persons of different genders, races and ethnicities that are not explainable by objective factors such as performance, experience level, credentials, or location, and are committed to correcting any issues and reviewing practices from unintended outcomes.

Commitment to Equal Opportunity

HealthJoy is committed to creating a diverse environment and is proud to be an equal opportunity employer.

All qualified applicants receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or any other basis forbidden under federal, state, or local law.

Don’t meet every single requirement? We know the confidence gap and imposter syndrome can get in the way of meeting spectacular candidates, so please don’t hesitate to apply — we’d love to hear from you. HealthJoy is dedicated to building a diverse, inclusive, and authentic workplace, so if you’re excited about this role and HealthJoy, we encourage you to apply. You may be just the right candidate for this or other roles.