Director, Product Management OTR Payments & Experience (Chicago)

Director, Product Management OTR Payments & Experience

Location

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.

About WEX & The Role

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, youll be tasked with protecting WEXs industry-leading position in fleet payments while ensuring our solutions evolve with changing market needs and competitive threats. Youll lead a team that ensures system performance today and positions WEX to outpace disruption and unlock new value for tomorrow.

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. Youll 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 Youll 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 effortsreducing 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 impactand report to leadership with clarity and context

• Anticipate and respond to industry shifts or competitive movements that may challenge WEXs leadershi

How Youll 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 disruptio

What Youll 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

• Bachelors degree required; MBA or advanced technical/business degree preferre

Why This Role Matters

WEXs OTR platform powers one of the largest payment systems in the trucking industry. As Director, you will be responsible for ensuring that platform not only remains stable and competitivebut 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.

The base pay range represents the anticipated low and high end of the pay range for this position. Actual pay rates will vary and will be based on various factors, such as your qualifications, skills, competencies, and proficiency for the role. Base pay is one component of WEX's total compensation package. Most sales positions are eligible for commission under the terms of an applicable plan. Non-sales roles are typically eligible for a quarterly or annual bonus based on their role and applicable plan. 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. For more information, check out the About Us section. Pay Range: $177,000.00 - $235,000.00 #J-18808-Ljbffr