Job Description: Product Lead, Internal Systems & Automation

Location: Flexible (with co-working options available)

Compensation Range: $155,000 - $175,000 USD + Equity + Comprehensive Benefits

About the Company

This is a technology company on a mission to redefine a critical pillar of the American healthcare ecosystem. Over 20 million seniors rely on independent Medicare brokers for guidance, yet these advisors have been underserved by technology. Our company was founded to close this gap, providing these brokers with a world-class technology platform featuring an industry-leading CRM, AI-powered workflows, and dedicated client services. This empowers them to build the business of their dreams while helping more Americans access quality healthcare.

As the fastest-growing Medicare brokerage in the country, our platform supports over 8,000 brokers serving hundreds of thousands of beneficiaries. We are backed by top-tier investors and built by a talent-dense team with experience from leading technology and healthcare companies. We are proud to have been recognized as one of Inc. Magazine's Best Workplaces, a testament to our commitment to employee well-being through generous benefits like flexible work, sabbaticals, and company retreats.

About the Role

We are transforming how Medicare agencies operate, and this role sits at the heart of that transformation. As a Product Lead, you will own the vision for automating the highly manual, error-prone workflows that power our most critical internal functions: broker payments, data reconciliation, onboarding, and compliance reporting.

This domain is one of the most technically and operationally complex in the company, involving hundreds of edge cases, fragmented data sources, and high-stakes financial flows that must "just work." You will be the strategic force that brings clarity to this complexity, designing the architecture for how data moves through our systems and building the automation foundation that ensures every broker gets paid faster and with greater accuracy.

What You'll Do

1. Own the Product Vision: Define and drive the long-term product strategy and roadmap for internal systems, broker payments, and operational automation.
2. Simplify Complexity: Develop a masterful understanding of end-to-end workflows—identifying where data breaks and designing resilient, scalable solutions.
3. Drive Cross-Functional Alignment: Partner closely with Engineering, Operations, Data, Finance, and Compliance to prioritize initiatives and design systems that meet diverse stakeholder needs.
4. Deliver Measurable Outcomes: Focus on key metrics such as reducing manual effort, accelerating payment cycles, and improving data accuracy across the platform.
5. Execute with Precision: Write detailed product specifications for high-leverage features, from ETL improvements to new automation tools.
6. Mentor and Scale: Help shape the product culture by mentoring other product managers and evolving our processes as the company grows.
7. Operate Hands-On: Dive deep into data models, analyze dashboards, and personally validate complex workflows to ensure quality and understanding.

What Makes You a Great Fit

1. Extensive experience managing the development of complex, web-based products.
2. A deep sense of ownership and accountability, with a proven ability to identify core problems and translate them into clear business objectives.
3. An analytical approach to feature development and prioritization, with comfort using SQL or similar tools for data exploration.
4. Exceptional written and oral communication skills, with experience managing senior internal stakeholders.
5. A proven ability to operate and thrive in ambiguous environments, bringing structure and clarity to nascent challenges.
6. Prior experience developing internal-facing tools or platforms is a significant plus.
7. A background in healthcare, insurtech, or another highly regulated industry is advantageous.

Why You Should Join

By joining this team, you will get in on the ground floor of a fast-moving, well-funded, and mission-driven company where your work will have a profound impact on the brokers and beneficiaries we serve. You'll have the opportunity to learn, grow, be challenged, and have fun while doing it.

We are committed to supporting your happiness, health, and overall well-being with a comprehensive benefits package, including:

1. Equity compensation
2. Health, dental, and vision insurance
3. Flexible work location with co-working space access
4. 401(k) plan
5. Generous Paid Time Off and paid holidays
6. Monthly remote work stipend
7. Paid Parental Leave (up to 14 weeks)
8. A 2-week sabbatical for tenured employees at 5 years of service
9. Wellbeing perks and mental health resources

If you are excited to unknot deeply complex problems and shape the next era of insurance technology, we encourage you to apply.

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