Senior Manager, Product Management - OTR Payments & Experience

Location

Remote, with a requirement to reside within 30 miles of one of the following locations: Portland, ME; Boston, MA; Chicago, IL; Washington, DC; Dallas, TX; or San Jose, CA.

WEX is a leading payments and technology company dedicated to simplifying business operations through innovative financial solutions. As part of our Over-the-Road (OTR) line of business, we are seeking a Senior Manager, Product Management - OTR Payments & Experience to lead and support the evolution of our core payment platforms and digital customer experiences.

This role is ideal for a strong operator-someone who excels at managing complex, established systems, ensuring their performance, and leading a team to maintain and evolve critical infrastructure. This position is less about building entirely new products and more about stewarding the platforms that are foundational to our OTR business, while helping guide a roadmap for incremental improvement and modernization.

The OTR Payments & Experience team is responsible for the products that power transaction processing, fraud prevention, fleet payment workflows, and customer-facing digital tools. As Senior Manager, you will lead a team of product managers focused on these areas, working cross-functionally with engineering, risk, sales, and operations to ensure the systems remain reliable, secure, and user-friendly-while also driving modernization over time.

• Lead, coach, and develop a team of product managers supporting WEX's OTR payments platform and customer-facing experiences.

• Own the product strategy and roadmap for legacy systems, balancing the need for operational stability with modernization goals.

• Collaborate across technology, risk, operations, and business teams to prioritize enhancements, reduce technical debt, and improve overall system performance.

• Use data, customer feedback, and internal input to inform decisions and continuously improve the platform's functionality and usability.

• Identify opportunities for efficiency, scalability, and experience improvement without disrupting core transaction performance.

• Ensure compliance with regulatory, security, and operational standards across supported platforms.

• Build alignment across stakeholders and serve as a key voice in shaping the future of OTR payment systems and digital tools.

• Operational Stewardship: Take ownership of critical platforms, ensuring they run reliably and support day-to-day business needs.

• Team Leadership: Manage and mentor product managers, fostering clarity, accountability, and growth.

• Cross-Functional Alignment: Work closely with technology, commercial, and operational partners to align priorities and deliver value.

• Strategic Thinking: Develop a clear, phased roadmap for modernization that aligns with business goals.

• Customer-Driven Mindset: Advocate for fleet customers by improving their experience across the web and mobile platforms.

• 8+ years of product management experience, with at least 2+ years in a people leadership role.

• Demonstrated success managing legacy platforms or core operational systems in fintech, mobility, logistics, or B2B SaaS.

• Deep understanding of payments, transaction flows, platform dependencies, and fraud prevention systems.

• Strong analytical and communication skills; able to translate technical complexity into business value.

• Experience improving systems incrementally while planning for larger modernization efforts.

• Collaborative approach with experience managing cross-functional initiatives.

• Familiarity with the OTR/trucking or transportation industry is highly preferred.

• Bachelor's degree required; advanced degree a plus.

WEX's OTR payment platforms are the backbone of our business-and they require strong leadership to maintain and evolve. This role ensures we meet the needs of today's customers while preparing our systems for tomorrow. If you're passionate about leading teams, optimizing complex systems, and driving thoughtful innovation, we'd love to hear from you.