Principal Product Manager - Steerage & Financial Incentives

Come for the mission. Stay for the innovation.

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

Healthcare benefits are complex and largely underutilized by most people. That’s why HealthJoy was built with one vision: to remove the complexity from being healthy and well. We do that by guiding employees to affordable, high-quality healthcare, consolidating our clients’ health and wellness strategies into the HealthJoy Benefits Operating System - a simple, unified digital experience. The result: healthier employees and a healthier bottom line.

HealthJoy is at the forefront of using AI 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. Our team is passionate about creating a more equitable and understandable benefits experience, while saving our clients time and money.

HealthJoy has garnered workplace awards from Inc.'s Fastest Growing Startups and Built In Chicago's Best Places to Work while growing globally to over 300 team members. We're continuing down the path of high growth and high impact — and this role is one of the most consequential bets we're making.

The Opportunity.

Healthcare costs are rising and employers are demanding real solutions with proven savings.

HealthJoy is extending its industry-leading engagement platform into a new product category that pairs financial incentives directly with our existing capabilities. The market for this model is validated and growing. Our position to win it is strong: years of member engagement data, deep integration across the benefits ecosystem, and infrastructure that standalone competitors can't replicate.

We're offering someone the chance to build a product line from scratch inside a company with real distribution, real data, and real backing. If you do it well — if the product is compliant, makes money, wins in the market, works for employers, and works for members — the natural next step is running it. The opportunity is for this role to grow into a General Manager position as the product scales.

Your Impact.

You are accountable for the success of this product as a business. That means it has to be compliant, financially sound, compelling to brokers and consultants, operationally deliverable for clients, and genuinely useful for members. All five. Not three of five.

You don't personally build everything that makes this product work. HealthJoy has teams and institutional knowledge across member experience, clinical programs, data science, and provider quality that will feed into this product. What you own is the product line itself — its architecture, commercial logic, compliance posture, market narrative, and outcomes. You know what each dependent capability needs to deliver for this product to win. You influence the teams that own those capabilities. You are accountable for the result regardless.

Stand the product up. Decide what we build, what we buy, and what we partner for. Evaluate and select the infrastructure partners that make the product work. Drive open questions and decisions across regulatory structure, financial model, and operational design. There is groundwork done, and many hard calls yet to be made. 

Design the incentive and compliance architecture. Own the structure of how members are rewarded, what triggers reimbursement, and how the product stays compliant across a complex regulatory landscape. Work closely with legal and benefits counsel. Lead those conversations, don’t just receive them.

Make the financial model work. Understand the unit economics well enough to pressure-test them, represent them credibly to CFOs and benefits consultants, and know when the numbers are wrong. Collaborate with finance on underwriting assumptions and risk structure. You don't need to be an actuary. You need to be the person in the room who catches it when the model breaks.

Hold the behavior change layer accountable. Member behavior is what makes the financial model work. The teams and systems that drive that behavior already exist at HealthJoy. Your job is to define precisely what those capabilities need to accomplish for this product — which journeys matter, what influence looks like at the moments that count, how results get measured — and drive those outcomes through the teams that own them.

Build the GTM plan and the market narrative. Work with Product Marketing and Commercial to develop positioning, sales enablement, and the story that lands in the broker and consultant channel. You'll help write it. You'll need to be able to deliver it yourself.

Define and own the proof layer. Set the operational standards the product is held to. Own the ROI story that drives retention and expansion. Make sure the renewal conversation is about demonstrated value.

Influence crossfunctionally. This role is the connective tissue across a wide dependency set. You won't have formal authority over most of these teams. You will need enough credibility, clarity, and commercial conviction to lead them anyway.  (Teams including Clinical Programs & Member Experience, Engineering & Data, Finance, Legal & Compliance,  Network & External Partners, and Product Marketing & Sales.)

Your Experience.

We care more about how you think and what you've built than where you've been.

10+ years of product management experience , with meaningful time operating at a senior or principal level. You’ve been the most senior PM on a product, not one of several with a Group Product Manager above you. A Bachelor's degree or equivalent experience is expected; an MBA or background in healthcare, law, or finance is a plus, not a requirement.

Domain background that shortens the learning curve . Healthcare, benefits, insurance, or fintech experience is a real advantage here. The compliance and financial dimensions of this product have stakes and a learning curve that pure consumer or SaaS PM experience doesn't prepare you for. 

A track record of standing things up . You've launched something that didn't exist before — with partner dependencies, regulatory constraints, and commercial pressure — and you own the full arc of what happened. Healthcare, benefits, or fintech experience is a meaningful advantage. The compliance and financial dimensions of this product have real stakes and the learning curve is real.

Business owner instincts, not feature owner instincts. You think in terms of whether the product makes money, wins in the market, and works for customers. You can hold the P&L logic and the product detail simultaneously without losing either.

Compliance-adjacent fluency. You don't need a JD. You need to be the kind of person who researches, forms a view, and leads the conversation with counsel — not the kind who waits for legal to tell you what's possible.

Financial modeling depth. You understand unit economics, can stress-test a pricing framework, and can explain the same financial story to a CFO and a benefits consultant in the same week without changing what you believe.

Organizational influence without authority. You've led outcomes across teams you don't manage. You know how to make people want to solve your problem without needing the org chart to back you up.

GTM instincts for channel-driven markets. You've launched products where the buyer isn't the end user and the channel has outsized influence on the sale. You know what brokers and consultants need to hear and how to build that into the product and the narrative.

AI fluency. You use AI tools to move faster across research, synthesis, spec drafting, and competitive analysis. You have a genuine point of view on how AI-powered personalization and recommendation should work in a regulated healthcare context.

Communication that's direct and calibrated . You can write a tight product brief and a compliance memo. You can present a pricing model to a CFO and a member journey to a clinical team.

This Role Is Not For Everyone

There is no established playbook for this product. The hard questions are real, and you'll be expected to drive them to decisions.

The cross-functional surface area is wide and formal authority is limited. You'll need to lead teams whose priorities you don't control toward outcomes you're accountable for. That's a different operating model than a traditional PM role.

If you do your best work when scope is clear, handoffs are defined, and someone else owns the hard calls — this isn't the job.

If building something consequential from scratch, inside a company with the assets to win, with a real path to running it as a business — sounds like exactly what you've been looking for — keep going.

Reporting & Growth Path

This role reports directly to the Chief Product Officer. You'll operate with significant autonomy and direct access to executive leadership, legal, finance, and commercial teams.

The growth path is explicit: as this product scales, this role is the natural foundation for a General Manager position with full P&L accountability. We're offering the chance to build toward that in a place where the distribution, data, and backing are already there.

We operate an open calendar policy: if you need time with someone, add it.

Total Rewards 

Job Level:  50

Minimum salary for this position: $170,000+, commensurate with experience.

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.