Product Design Architect, HealthJoy
$145-175k
Senior level
Remote from US
Health benefits platform for employers
Be an early applicant
Health benefits platform for employers
201-500 employees
HealthcareB2BEnterpriseHR
Be an early applicant
$145-175k
Senior level
Remote from US
201-500 employees
HealthcareB2BEnterpriseHR
Company mission
To simplify the healthcare experience by removing the complexity from being healthy and well.
Role
Who you are
- 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
- 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
What the job involves
- 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
- 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
- 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
- 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
Our take
Although shopping around for a car or mortgage is standard practice, when it comes to medical procedures, people often take what they are given. HealthJoy is a company that helps employees shop around for the most cost-effective healthcare options, then rewards these employees when they take the lower-cost option.
The HealthJoy benefits experience platform combines a chatbot with artificial intelligence along with human input to settle on the most affordable available treatment for employee. Savings are then shared with the employee via a savings account or gift card. HealthJoy focuses on providing its services to larger companies, with tens of thousands of users, but has expressed intentions to work with small and medium-sized businesses in the future.
As healthcare costs continue to rise, HealthJoy is ready for continued success by helping employers manage expenses and improve employee care. With a strong track record and strategic partnerships, the company is set to deliver lasting value as demand for affordable, high-quality care grows.
Kirsty
Company Specialist at Welcome to the Jungle
Insights
Top investors
7% employee growth in 12 months
Company
Funding (last 2 of 5 rounds)
Oct 2022
$60m
SERIES D
Feb 2020
$30m
SERIES C
Total funding: $108.5m
Company benefits
- Remote Work: Being a remote-first company, we give new employees a remote work stipend to ensure you can work comfortably from home
- Health & Wellness: We offer healthcare benefits including medical, dental, vision, therapy, HSA contribution match, EAP, telemedicine, virtual exercise therapy, and disability
- Company Events: We provide our employees with virtual-lunch-and-learns, virtual coffee chats, happy hours, and quarterly team activities
- Financial Wellness: We offer equity with our Stock Option Distribution Policy, 401k match, and an employee referral bonus program
- Recharge: HealthJoy provides employees the freedom they need to balance the responsibilities of both their work and home lives. We offer flexible PTO, paid holidays, parental leave, and more
Company HQ
River North, Chicago, IL
Leadership
Justin Holland
(Co-Founder & CEO)Having studied at MIT, they co-founded FreeCause in 2006 and OpenInstall in January 2011. They then spent 1 year as VP Platform at AVG before founding HealthJoy as CEO in March 2014.
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