Head of Digital Operations, Innovation and Strategy

Role: Head of Digital Innovation, Strategy and Operations 

Reports to: Chief Digital Officer

Location: Preferred locations are Portland, ME, Boston, MA and Dallas, TX

About WEX

WEX is an innovative benefits, payments and technology company looking to forge the way in a rapidly changing environment, with a goal to simplify the business of doing business for our customers, freeing them to spend more time, with less worry, on the things they love. The Digital team, consisting of Product Management, Design, Product Marketing, and Data, Analytics & AI, is leading WEX’s efforts to create innovative experiences, supported by new operating and business models, while delivering the products to meet near term needs.  From proactive insights to AI agents to eliminate work, we are reimagining the end to end experience for customers.  

As the Head of Digital Operations, Innovation and Strategy, you’ll be in the thick of the action, helping drive our Digital agenda and strategy to create long term growth and deliver products that delight our customers. We are seeking an inspirational leader to partner with the Chief Digital Officer to define our digital strategy, innovate to create new offerings and new business models and help the Digital org elevate its productivity, ensuring we are delivering on the most important imperatives with efficiency and agility.  This role will also be responsible for driving the transformation to a product-centric operating model, aligned with best in class product and software development principles across our organization. This role includes three verticals - Digital Strategy, Innovation and Enablement, and Strategic Operations, overseeing a team of 10-15.

The ideal candidate will be both a strategic thinker and an execution-focused leader, enabling WEX’s transition to a more agile, customer-focused, and scalable product culture while setting the vision to drive future growth. You have demonstrated experience in leading large-scale transformations, moving organizations from project-based to product-based operating models. You are passionate about developing and mentoring people across the organization, ensuring they have the tools, skills, and mindset necessary to drive continuous innovation and customer-centricity. 

Responsibilities include:

• Define and Drive Digital Strategy: Partner with Corporate Strategy, Digital, Commercial leaders to build compelling digital strategies that ladder up to - and shape - WEX’s overall vision and priorities. 

• Lead Innovation: Oversee team driving innovation process management, embedding a structured framework for continuous improvement and measurable impact. As part of the innovation team, build out a small number of specialized, ring fenced teams focused on high-priority, transformative projects with the agility and freedom to explore disruptive ideas. Drive a culture of experimentation, bringing ideas from concept to pilot with cross-functional collaboration, while maintaining alignment with strategic goals. 

• Build Digital & Product Enablement: Lead an Enablement team dedicated to embedding a product-centric, outcome-driven operating model across WEX. In partnership with HR, drive upskilling for digital and strategy leaders, enabling them to shape impactful, customer-centered product strategies. Foster a learning culture that emphasizes continuous improvement, collaboration, and clarity on measurable results, aligning day-to-day priorities with WEX’s long-term vision. Through coaching and a framework grounded in best practices, empower teams to deliver exceptional, market-differentiating products.

• Accelerate Delivery and Insights: Partner closely with the Chief Digital Officer (CDO) to monitor and advance key strategic imperatives, translating their progress into actionable insights and focused priorities. This includes 

  • optimizing Digital (with Tech) organizational processes to drive efficiency and ensuring alignment with quarterly CDO goals. 

  • Driving agility in decision making 

  • partnering closely with finance on aligning our strategies to our capital investments and ensuring ongoing operational rigor to assess progress y maintaining a pulse on project status and streamlining execution, you’ll contribute to more agile delivery, better decision-making, and a sharper focus on initiatives that propel WEX’s digital transformation forward.  Assist with quarterly updates of CDO goals in accorda