Staff Product Manager, Payments

About the role:

As a Product Manager on our Core Insurance Product team supporting Payments your scope will encompass accurately processing payments and identifying different payment constructs to create differentiated customer experiences and directly influencing company growth - along with the key business outcomes this drives. You'll be accountable for owning the end-to-end flow from claim submission through payment receipt and reconciliation — which directly translates to providers and patients having seamless experiences without surprise charges or delays. Partnering closely with Engineering, Data, Operations, and Finance, you'll tackle complex technical challenges in insurance platform, while building tools and user experiences that scale with our rapidly growing provider network and improve the experience for every provider and patient we serve.  

What you'll do at Headway:

• Own the strategy and roadmap for our one of our core insurance platforms - spanning claims processing, benefits verification and/or payment disbursement - driving down loss and directly impacting company revenue and user satisfaction
• Design workflows that balance automated processing with robust exception handling, ensuring high success rates while minimizing manual intervention
• Drive technical decisions on platform architecture with Engineering teams to optimize success rates
• Lead cross-team initiatives to reduce errors and improve accuracy to reduce financial leakage, partnering with Operations, Finance, and Data teams to identify trends, detect anomalies, and build predictive models for proactive issue prevention. 
• Identify and fix customer experience breakdowns for patients and providers — tracing pain points from their origin in backend systems through to the user-facing moment, and driving resolution across teams to deliver measurably better outcomes
• Build internal tools that empower our Operations team to investigate complex issues, manage denials, and scale efficiently with business growth

You'll be great for this role if you:

• Platform and processing experience: You have 7+ years building high-volume transaction platforms or managing complex financial/billing systems, preferably in healthcare, fintech, or B2B marketplaces
• Customer-focused approach: You understand how to translate complex backend systems into great user experiences and have built features for both external users (providers and patients) and internal teams (operations, support)
• End-to-end funnel ownership: You have a track record of mapping and improving complete customer journeys — from the moment a patient books or a provider submits a claim, through to final resolution. You identify where patients and providers fall off, experience friction, or receive unexpected outcomes, and you build the systems and workflows to fix it at scale
• Internal tooling expertise: You understand how to build tools for internal teams and have experience with workflow automation, exception handling, and operational scalability
• Technical depth: You're comfortable diving deep with engineering teams on integration challenges, data pipelines, and can drive architectural decisions for platforms processing critical data. Familiarity with AI/ML applications — such as predictive denial models, anomaly detection, or intelligent triage — is a strong plus
• Cross-functional leadership: You've led initiatives requiring coordination across multiple teams and can balance technical complexity with business requirements and operational needs

Analytical mindset: You can extract insights from complex data, identify patterns in business performance, and use metrics to drive product decisions and process improvements

Compensation and Benefits:

The expected base pay range for this position is $212,000 - $265,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

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