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 accordance.

• Craft our narrative: Connect and communicate the strategic story of our Digital growth and priorities across our internal and external partners to amplify our Digital story; partner with Comms, IR, and Marketing to ensure effective execution and activation. Proactively define proof points to amplify the credibility and impact.

• Drive Executive Content: Provide high level support to CDO in telling Digital’s story across various forums, including preparing presentations, reports, and other materials for executive meetings, Board of Directors, internal and external speaking events (e.g., Spark, Ignite), customer presentations, earnings etc. Partner across org to drive strategic alignment, consistent messaging, review cycles and on-time delivery. For quarterly Board meetings, partner with Digital Strategy on material creation and for external / mainstage events, partner with External Comms and Marketing.

• Serve as Trusted Advisor: Partner with the CDO to identify key opportunities to drive growth, improve efficiency, build culture, tell our story and otherwise achieve our objectives.

• Build Culture and Employee Engagement: In partnership with HR, foster an innovative and high-performance culture within the Digital team, planning activities and events that boost engagement, collaboration, and employee satisfaction.

Must have

• 15+ years of experience ideally with 1-3 years of experience in consulting; experience in product management, customer driven innovation, digital marketing, AI or related fields a plus.

• Exceptional cross-organization coordination and communication skills including ability to build comprehensive and compelling presentation and communication materials that span functions and groups, including C-suite and Board level presentations

• Demonstrated ability to influence executive leadership on complex business topics.

• Ability to balance varying responsibilities that span rhythm of business, communications, executive management, and culture.

• Systems thinker, able to manage a high degree of complexity and to distill information into simple messages, able to think both strategically at a global level as well as effectively developing key processes.

• Demonstrated experience leading large-scale change initiatives, with the ability to inspire and engage diverse stakeholders to ensure engagement and optimal adoption.

• Strong project management skills and ability to lead multiple high-profile projects of varying timelines simultaneously, with strong sense of urgency and delivering to deadlines.

• Strong interpersonal skills including ability to build trust, influence, and foster relationships with diverse team members; ability to leverage relationships to drive consistency of approach and ensure delivery.

• Passion to foster a culture of innovation and high performance through initiatives, training & education, and communication.

• A solid team player who’s also an independent thinker and executor.

• A robust analytical skill set, an endless curiosity and a penchant for thinking about “art of the possible”.

• Strong financial acumen.

• A strong sense of ownership in your work.

• Hunger to sprint/hustle from one project to the next, and iterate quickly.

• Comfortable with ambiguous, changing situations, and decision making.

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: $216,000.00 - $287,000.00