Head of Mobility Program Management

WEX•Portland, ME

About The Position

The Head of Mobility Program Management is a critical execution leader within WEX, serving as a strategic partner to Technology and Digital Mobility leadership. You will move beyond traditional coordination to create clarity, drive delivery accountability, and accelerate execution. You will champion an operational style that balances execution empathy with strict data hygiene, automated governance, and outcome-focused delivery. You will be responsible for leading and overseeing a team of Technical Program Managers, ensuring the successful planning, execution, and delivery of key initiatives. In this role, you will drive delivery to maintain our status as the leading payments, financing, and services platform powering businesses in the field and on the road. The Technology Innovation & Strategic Operations (TISO) office is an enabling team focused on driving innovation, software quality, and excellence. We invest in talent development, data-driven insights, and flow engineering to align technology with business goals.

Requirements

BS/BA Degree in technical/information science or a related field, or equivalent experience
10+ years of relevant experience in program management
At least 3+ years of experience in a leadership role overseeing a team of Technical Program Managers.
Strong technical acumen with a deep understanding of the software development lifecycle (SDLC).
Must be "technical enough" to facilitate complex engineering discussions and bridge the gap between technical execution and business requirements to help define technical requirements.
Responsible for proactively identifying technical risks and dependencies.
Expertise in Agile methodologies (e.g., Scrum, SAFe) and Atlassian suite of products
Experience in designing and executing agentic development lifecycle-aligned (ADLC) governance models.
Proven ability to maintain rigorous data hygiene and leverage tool proficiency to drive automated, data-driven decision-making.
Strong business acumen and industry awareness within Mobility products expected
Exceptional leadership skills with a proven track record of driving accountability for outcomes.
Experience navigating complex organizational structures and coaching teams to bridge the gap between technical execution and business value.

Responsibilities

Co-develop the strategic roadmap with Technology and Digital leadership, ensuring rigorous alignment with business goals.
Facilitate tradeoff conversations that validate technical feasibility and capacity, ensuring the organization prioritizes high-impact outcomes over output and mitigates overcommitment.
Drive dependency resolution and escalate and unblock issues with the goal of increasing delivery confidence.
Orchestrate continuous planning rituals that bridge strategy and development.
Establish automated, transparent visibility into program health through rigorous Jira data integrity - enabling real-time reporting on capacity, release status, and bottlenecks.
Prepare and leverage delivery metrics to drive decision making.
Champion clear quality and governance standards for all plans.
Ensure TPMs act as end-to-end owners who facilitate cross-functional alignment and process discipline.
Coach your team to serve as orchestrators of AI-augmented workflows.
Drive the maturity of our agentic development lifecycle by ensuring teams maintain the foundational context, specifications, and data discipline required for agentic success.
Focus on outcome-based visibility, showcasing progress against quarterly enterprise priorities.
Build internal/external networks to break down organizational silos.
Act as the "voice of the project" through automated reporting.
Recruit, mentor, and retain top-tier technical talent.
Foster an inclusive, mission-driven environment while continuing our talent transformation to expand the team's capabilities.