Product Design Architect

HealthJoy

1d•Remote

About The Position

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.

Requirements

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.