Head of Strategy & Business Operations, Work Management

Director of Strategic Operations is a senior leader who serves as a strategic thought partner to the SVP of Customer Success & Value Realization and brings the operational rigor, accountability, and execution discipline that turns strategy into impact. This leader works alongside the SVP to develop and sharpen the strategy for the organization, and then makes it run—translating it into clear plans, operating rhythms, and tracked commitments across Professional Services, onboarding/implementation, partner implementation, and learning/enablement.They are senior enough to help shape the strategy itself—bringing analysis, perspective, and well-formed options to the table and pressure-testing the SVP’s thinking—and hands-on enough to drive the day-to-day execution, cadence, and follow-through that deliver measurable outcomes. this leader helps create the thinking behind them and is accountable for making them happen.This role gives the SVP both leverage and a true operating partner: more bandwidth to lead, sharper visibility into performance, stronger thinking on the hardest problems, and confidence that priorities are moving and commitments are being met.The SVP has a trusted operating partner who strengthens the quality of the strategy and the decisions behind it.Performance is visible early, so risks and issues surface in time to act on them.Essential Duties and ResponsibilitiesStrategy Development & Thought Partnership - 20%Partner with the SVP to develop and sharpen the strategy for the organization—bringing analysis, market and customer perspective, and well-formed options to inform the SVP’s decisions.Pressure-test the SVP’s thinking and surface the questions, tradeoffs, and risks that lead to better decisions; Frame complex, ambiguous problems into clear choices and recommendations, helping shape where the organization should focus and why.Bring structure, focus, and momentum to complex, high-ambiguity initiatives so they stay on track and get finished.Operating Rhythm & Cadence - 15%Build and run the operating rhythm for the organization—leadership meetings, business reviews, escalation forums, and cross-functional check-ins—that keep teams aligned and accountable.Prepare and synthesize materials for SLT/ELT and Board reviews on the SVP's behalf, turning complex performance and strategy into clear, decision-ready narratives.Performance Visibility & Insight - 15%Build and maintain the reporting and dashboards that give the SVP and leadership team timely visibility into delivery, implementation health, value realization, customer satisfaction (NPS, retention trends), and operational performance.Turn data into insight and recommendation, not just reporting—flag gaps, risks, and where attention is needed so issues surface early enough to act on.Standardize metric definitions and reporting across teams so performance is measured consistently.Cross-Functional Program Leadership - 15%Lead high-priority, cross-functional initiatives on the SVP’s behalf, managing timelines, risks, dependencies, and outcomes through to delivery.Serve as a trusted, dependable point of coordination across all functions of the business - e.g. Sales, Account Mgmt / Growth, CRV, Product, Tech, Finance, Marketing, Legal, HR.Operating Model & Economics Support - 10%Partner with the SVP to develop the customer value operating model—helping shape how functions should connect, where handoffs and accountabilities need to be clearer, and bringing forward options for how the model should evolve.Work with Finance, Rev Ops, and CRV leadership to build the data and analysis behind the organization’s economics, keeping external revenue, cost allocation, ARR influence, and value attribution distinct rather than commingled.Prepare the analysis, materials, and options that inform the SVP’s decisions on the model, investment tradeoffs, and priorities.Continuous Improvement & Ways of Working - 5%Identify and implement better ways of working that improve how the organization operates, leveraging tools, automation, and practical AI solutions.Incorporate lessons learned, data, and customer feedback into operational adjustments, building a habit of continuous improvement.Knowledge, Skills, AbilitiesRequired QualificationsSignificant experience in strategic operations, chief-of-staff, strategy, or program leadership in a high-growth or complex matrixed environment, at a scope consistent with a Director / Sr. A strong track record both of helping shape strategy—bringing analysis, options, and judgment to senior decisions—and of making it run, turning priorities into plans, operating rhythms, and tracked commitments that deliver measurable outcomes.Strong analytical and problem-framing skills, with the ability to take ambiguous problems and turn them into clear choices, options, and recommendations.Proven ability to partner across functions and business areas to coordinate initiatives and drive accountability without owning those functions directly.A reputation for being collaborative, organized, analytical, proactive, and highly dependable—bringing structure to ambiguity and momentum to fast-paced environments.Required QualificationsExperience in Professional Services, implementation/onboarding, customer success, or value-realization functions.Deep customer-centricity, with experience using customer insight (NPS, retention drivers) to shape strategy and operational improvements.Experience building dashboards and performance frameworks and using data to inform decisions.Experience implementing process improvements, operating cadences, and continuous-improvement frameworks.Disclaimer: This description may not be exhaustive of all of the possible responsibilities, tasks, duties and/or qualifications of the role and the Company reserves the right to assign other responsibilities, tasks, duties and/or qualifications from time to time in the future in accordance with applicable law.The base pay range represents the anticipated low and high end of the pay range for this position. 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. Pay Range: $171,100.00 - $207,000.00SummaryLocation: Portland, METype: Full time