Director, Product Management - OTR Payments & Experience

Location

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

About WEX & The Role

WEX is a leading payments and mobility platform that helps 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.

About the Team & Impact

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.

What You’ll Do

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.

How You’ll Lead

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.

What You’ll Bring

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; MBA or advanced technical / business degree preferred.

Why This Role Matters

WEX’s OTR platform powers one of the largest payment systems in the trucking industry. As Director, you will be responsible for ensuring that the platform not only remains stable and competitive but evolves in ways that secure our market position and unlock future growth. This is a pivotal role for a product leader who thrives in complexity, leads with clarity, and sees transformation as both a challenge and an opportunity.

Pay Range : $177,000.00 – $235,000.00

WEX’s comprehensive and market competitive benefits are designed to support your personal and professional well‑being. Benefits include health, dental and vision insurances, retirement savings plan, paid time off, health savings account, flexible spending accounts, life insurance, disability insurance, tuition reimbursement, and more.

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