Product Manager - ICHRA

When Product Manager - ICHRA Remote · Full time Apply for Product Manager - ICHRA Product Manager

About When When is a US-based, venture-backed company that has built a novel AI-driven health insurance marketplace and post-employment platform. Our product will transform how companies offboard employees and how people manage their transition between jobs. Description The Opportunity

We are currently hiring for a Product Manager - ICHRA , focused on our ICHRA (Individual Coverage Health Reimbursement Arrangement) solution. Reporting to the VP of Product, this is a high-impact, foundational role. You will own the ICHRA product from its current MVP state through future phases of growth and expansion.

ICHRA is one of the fastest-growing benefits strategies in the market, and we're building a category-defining product. You don't need to be an ICHRA expert on day one, but you should be energized by the idea of becoming one — and by the opportunity to shape a complex, evolving product that touches compliance, employer benefits, health insurance, and payments.

At When, we're an AI-forward company. That means AI isn't just in our product — it's embedded in how we work. We expect our team members to actively leverage AI tools throughout the product development lifecycle, from research and requirements to execution and iteration. Comfort and fluency with tools like Claude, JIRA, Confluence, Notion, and Figma is essential.

Role Overview

The person in this role will partner closely with our product, engineering, operations, and leadership teams to define, prioritize, and execute on the ICHRA product roadmap. You will be the connective tissue between business strategy and technical execution — translating employer and employee needs into clear product requirements and driving delivery with a distributed team.

Responsibilities

• Own the ICHRA product roadmap from MVP refinement through future phases partnering with the VP of Product and leadership to set vision, strategy, and priorities.
• Develop clear, actionable product and feature requirements for both incremental improvements and 0-to-1 launches. Collaborate with stakeholders, design, and engineering to ensure high-quality, well-scoped delivery.
• Drive end-to-end execution: planning, documentation, development tracking, QA, and launch with a bias toward speed and quality.
• Champion AI-forward product development practices and actively using tools like Claude, JIRA, Notion, and Figma to accelerate research, documentation, and iteration throughout the product lifecycle.
• Lead and participate in Product & Engineering planning, check-in rituals to promote development best practices across the team.
• Become a subject-matter expert in ICHRA; including compliance requirements, employer and employee workflows, integration patterns, and the competitive landscape.
• Collect, synthesize, and prioritize internal and external product feedback, translating insights into roadmap decisions.
• Define KPIs and establish product analytics practices to measure outcomes and surface opportunities for improvement.
• Maintain strong cross-functional communication, keeping leaders and stakeholders aligned on priorities, progress, and decisions.
• In partnership with the VP of Product and CTO, propose and implement improvements to the product development cycle to accelerate high-quality delivery.
• Be a nimble team player who is comfortable wearing different hats, embracing ambiguity, and contributing to a positive remote team culture.

Qualifications

Required

• Bachelor's Degree
• 3+ years of experience in Product Management, working within an Agile framework
• Demonstrated ability to take a product from early-stage through iterative development cycles
• Fluency with AI tools (e.g., Claude, ChatGPT) and product/project management platforms (e.g., JIRA, Notion, Figma, GitLab) not just familiarity, but active, day-to-day usage
• Strong organizational, prioritization, communication, and cross-functional collaboration skills
• Comfort working in a fast-paced startup environment, managing multiple priorities simultaneously
• Comfortable working remotely and communicating effectively across distributed teams, partners, and clients

Preferred

• Experience with employer benefits, health insurance, HRAs (ICHRA/QSEHRA), payments, compliance, or account-based benefits
• Prior exposure to ICHRA either as a product builder, operator, or practitioner is a meaningful plus
• Experience navigating regulated industries (ACA, HIPAA, ERISA, or similar compliance environments)
• Demonstrated experience using AI to accelerate product discovery, documentation, or delivery

Compensation:

We offer a competitive salary, we pay 100% of your health insurance, stock options and more!

Location & Travel :

Remote with minimal travel to attend company and occasional client meetings.

The salary range for this position is: $105,000 - $140,000. When considers a variety of factors when determining base compensation, including experience, qualifications, and geographic location. Actual compensation will vary based on these considerations.

Salary $105,000 - $140,000 per year

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