Director, Product Management - Owner-Operator Solutions (Chicago)

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 global payments and mobility platform committed to delivering innovative solutions to businesses that keep the world moving. Within our Over-the-Road (OTR) line of business, we are seeking a Director, Product Management Owner-Operator Solutions to lead the strategy, team, and product direction for a growing portfolio of digital products designed to serve small fleets and independent drivers.

This role offers the opportunity to lead a cross-functional product area with full accountability for customer experience, product performance, and long-term growth. The Director will be responsible for driving adoption, expanding offerings beyond fuel, and delivering meaningful value to the owner-operator segment.

About the Team & Impact

WEXs owner-operator product portfolio delivers digital-first, user-friendly solutions that simplify operations and financial management for independent drivers and small fleets. With a strong foundation in fueling and payments, the platform is evolving to address broader customer needs. As Director, you will set the vision, define product strategy, and lead execution to expand adoption and product impact in this space.

How You'll Make an Impact

• Own the vision, strategy, and roadmap for owner-operator solutions, aligning with business goals and evolving customer needs.

• Build and lead a high-performing product team, setting direction, driving execution, and supporting team development.

• Drive adoption, engagement, and revenue growth through continuous improvement and user-centric design.

• Identify and execute on opportunities to expand beyond fuel, such as offerings in maintenance, factoring, insurance, compliance, and financial wellness.

• Partner with engineering, design, marketing, sales, and operations to deliver intuitive, high-impact products.

• Evaluate and pursue external partnerships and integrations that enhance platform value.

• Act as the internal voice of the owner-operator customer, advocating for their needs and experience.

• Track product performance and communicate progress to stakeholders with clarity and transparency

How Youll Lead

• Business-Minded: You think holistically about customer experience, product value, and growth strategy.

• Team-Builder: You create clarity, accountability, and momentum within a collaborative team environment.

• Customer-Centric: You prioritize features and improvements based on real customer insight and outcomes.

• Cross-Functional Influencer: You align diverse teams around shared goals and navigate complexity with confidence.

• Outcome-Oriented: You drive measurable impact and keep results at the center of your decision-making

Experience You'll Bring

• 8+ years of product management experience, including 3+ years in a product leadership role.

• Experience with customer-facing digital platforms, ideally in fintech, logistics, mobility, or B2B SaaS.

• Demonstrated success in scaling product adoption, expanding into adjacent service areas, and driving customer value.

• Comfort operating in fast-paced, growth-stage environments, with an ability to balance short-term execution and long-term vision.

• Familiarity with the workflows and challenges of owner-operators, small fleets, or independent contractors is a strong plus.

• Strong strategic planning, communication, and cross-functional leadership skills.

• Bachelors degree required; MBA or advanced business/technical education preferred

Why This Role Matters

WEX is committed to helping owner-operators and small fleets thrive by delivering tools that simplify how they work and succeed. As Director of Product Management, youll lead a critical product portfolio, guide strategic expansion, and create solutions that deliver lasting value for customers and for WEX. If youre ready to lead with purpose and scale meaningful digital productswed love to hear from you.

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