Director, Product Management - OTR Payments & Experience

Director, Product Management - OTR Payments & Experience

This is a remote position, however, the candidate must reside within 30 miles of one of the following locations : Portland ME, Chicago IL, Boston MA, Washington DC, Dallas TX, San Jose CA, Seattle WA, or New York City NY.

WEX is a leading payments and mobility platform helping businesses streamline financial operations. Within our Over-the-Road (OTR) line of business, we are seeking a Director, Product Management - OTR Payments & Experience to lead the strategy, modernization, and performance of the platform that powers fleet payments, fraud controls, and digital customer interactions. This role is responsible for owning one of the most critical product areas in the company. As a business and platform leader, you'll be tasked with protecting WEX's industry-leading position in fleet payments while ensuring our solutions evolve with changing market needs and competitive threats. You'll lead a team that ensures system performance today and positions WEX to outpace disruption and unlock new value for tomorrow.

The OTR Payments & Experience team owns the products and platforms at the core of our OTR business. These include transaction processing, digital account management, fraud prevention, card controls, and key customer-facing workflows. You'll lead a team of product managers and work cross-functionally with engineering, operations, and risk to maintain reliability, improve usability, and modernize our capabilities in a competitive and evolving landscape.

Own the roadmap, strategy, and platform performance for OTR payments and digital experience systems

Lead a team of product managers, creating clarity, accountability, and execution focus

Champion modernization efforts-reducing technical debt, improving UX, and introducing scalable infrastructure

Monitor platform health and proactively identify system risks, inefficiencies, or emerging threats

Work closely with engineering, architecture, and operations to align investments and priorities

Explore new ways to extend customer value through enhancements, integrations, or commercial innovation

Act as the senior product voice in balancing short-term system needs with long-term product evolution

Track KPIs for platform performance, stability, and business impact-and report to leadership with clarity and context

Anticipate and respond to industry shifts or competitive movements that may challenge WEX's leadership

Platform Steward : You excel at managing complex, high-scale systems with a focus on uptime, resilience, and reliability

Strategic Modernizer : You can chart a long-term path from legacy to future-state without compromising the business

Cross-Functional Influencer : You build strong relationships across tech, risk, ops, and business teams

Outcome-Oriented : You define success with measurable impact and lead through results

Defensive & Offensive Strategist : You protect core value while expanding our offering and resisting disruption

8+ years of product management experience, including 3+ years in a product leadership or platform management role

Experience leading complex product lines that power business-critical operations

Background in fintech, payments, SaaS platforms, or transaction processing environments

Strong track record of platform stewardship and experience driving modernization efforts

Ability to influence technical and business leaders with data, insight, and judgment

Excellent communication skills and comfort operating across cross-functional and executive teams

Experience in OTR, transportation, or fleet-related services is highly preferred

Bachelor's degree required; M