Senior Product Manager, OTR Platform Modernization

WEX is an innovative payments and technology company leading the way in a rapidly changing environment. Our goal is to simplify the business of running a business for our customers and free them to spend more time, with less worry, on the things they love.  We are on a journey to build a unified, world class user experience across our products and services and leverage customer driven innovation to power our growth and  strategic initiatives.  

About the Role:

The Senior Product Manager independently owns the strategy, multi-year roadmap, and business outcomes for a critical digital platform modernization initiative for Over-The-Road (OTR) payments domain, driving the evolution of legacy systems into a unified, high-performance platform. As the product management landscape evolves, the line between product strategy and user experience continues to blur, which is why we are seeking a candidate who brings a hybrid mindset that blends strong product execution with foundational UX design thinking. In this role, you will leverage modern AI tools to accelerate discovery while working shoulder-to-shoulder with UX researchers and designers as a true co-creator of seamless user journeys. Your primary strength lies in navigating ambiguity, influencing senior leadership, and bridging engineering, design, and business teams to execute complex, high-visibility initiatives.

Key Qualifications & Skill Highlights:

• Strategic Vision & Multi-Year Road mapping: Proven ability to establish long-term product strategy, translate company objectives into actionable roadmaps, and independently lead complex, end-to-end Go-To-Market execution.

• Evolving Product & UX Hybrid Mindset: Deep passion for product-led UX design, customer journey mapping, and usability principles. Operates as an equal co-creator with UX design partners, bringing a design-thinking approach to product discovery and interface refinement.

• AI Tooling & Workflow Innovation: Advanced proficiency in leveraging generative AI tools and AI-driven platforms to accelerate discovery, automate spec documentation, analyze complex behavioral patterns, and evaluate intelligent feature integrations.

• Platform Modernization & Scalability: Track record of leading large-scale modernization initiatives, including sunsetting legacy systems, migrating complex customer workflows, and deploying modern digital solutions without operational disruption.

• Advanced Data & Analytics Proficiency: Expert in using interactive analytics tools and executive dashboards to uncover deep insights, measure post-launch adoption, and drive continuous, data-informed iterations.

• Strategic Influence & Mentorship: Experienced in driving organizational alignment across business stakeholders, engineering, UX, and executive leadership. Proven capability in guiding and mentoring junior PMs on product methodology, discovery frameworks, and strategic execution.

Required Qualifications:

• Undergraduate degree in business, computer science, design, or a related field.

• 8+ years of professional experience, with specific experience leading outcomes for complex, multi-faceted product initiatives.

• Demonstrated expertise in defining and leveraging product metrics to understand performance and deliver on strategic OKRs.

• Proven track record of close partnership with UX/UI design teams, integrating user-centered design directly into the product discovery lifecycle.

Preferred Qualifications:

• Master’s Degree in business, product management/development/marketing.

• Proven experience presenting to and influencing executive-level stakeholders.

• Experience in multi-quarter platform planning and complex Go-To-Market launches.

• Exposure to Over-The-Road (OTR) payments, commercial card systems, or fleet solutions domain.

• Agentic AI certification.