Vice President, IT Project Management Office

Trupanion is a leading provider of medical insurance for cats and dogs in North America. Our mission is to help loving, responsible pet owners budget and care for their pets. At Trupanion, we offer a collaborative, casual, and pet-friendly environment where everyone is encouraged to be themselves. *This position is open to candidates in the Seattle, WA area. You will have a hybrid remote/in-office schedule where you will work from our casual, pet-friendly office at least 3 days a week .* The Vice President, IT Portfolio & Project Management Office (PMO) serves on the technology leadership team and is responsible for driving execution across all areas of technology and gaining strategic alignment across the technology organization. Reporting directly to the CIO, this role serves as a critical strategic and operational partner—ensuring that technology strategy is translated into measurable outcomes, priorities are clear, and execution is disciplined, transparent, and predictable. This leader owns the IT PMO and acts as the connective tissue across Technology, Product, Finance, Security, Enterprise PMO, and Business leadership. They bring structure without bureaucracy, clarity without friction, and accountability without drama. Key Responsibilities Enterprise IT PMO Leadership Build, lead, and mature a best-in-class IT PMO supporting global, cross-functional initiatives Establish and enforce standard delivery frameworks (portfolio management, program governance, agile delivery, capacity planning, financial tracking, risk management, and benefits realization) Ensure consistent execution across large-scale initiatives (platform modernization, ERP, data, security, infrastructure, AI, and digital transformation) Drive delivery excellence across waterfall, agile, and hybrid execution models Strategic Partnership with the CIO Partner closely with the CIO to translate technology vision, strategy, and priorities into executable roadmaps Support CIO operating cadence: leadership meetings, executive reviews, steering committees, and strategic planning sessions Drive alignment across CIO direct reports and proactively resolve cross-team dependencies and execution risks Track and follow through on enterprise commitments, decisions, risks, and outcomes Portfolio, Financial & Value Management Own enterprise IT portfolio management, including intake, prioritization, sequencing, capacity planning, and dependency management Partner with Finance to manage IT investment governance, budgets, forecasts, and ROI tracking Establish clear metrics tied to business outcomes (delivery predictability, cost optimization, value realization, risk reduction) Executive & Board Engagement Prepare executive-level communications, dashboards, and materials for ELT, Board, and Audit/Risk Committees Ensure technology initiatives are communicated in business terms (outcomes, value, risk, tradeoffs) Support CIO in board, investor, and regulatory communications as needed Governance, Risk & Accountability Establish governance models that balance speed with appropriate controls Proactively identify delivery risks, execution gaps, and organizational bottlenecks Drive clear accountability while fostering a culture of trust, ownership, and continuous improvement Leadership & Talent Development Build and lead a high-performing PMO organization with strong program, portfolio, and delivery leaders Coach senior leaders on execution discipline, decision-making, and delivery rigor Serve as a role model for executive presence, communication, and cross-functional collaboration Required 15+ years of experience in technology delivery, program management, or enterprise transformation Bachelor’s degree in Business Administration, Management Information Systems (MIS), or related technical field Prior experience leading an enterprise or global PMO Proven track record partnering directly with C-suite executives, including CIOs Experience managing complex, multi-year technology programs with material financial and operational impact Strong financial acumen (budgeting, forecasting, ROI) Exceptional executive communication and stakeholder management skills 3+ years experience in JIRA Preferred Experience in regulated or complex environments (public company, SOX, PCI, HIPAA, etc.) Broad technology exposure across applications, infrastructure, data, and security MBA or advanced degree Leadership Attributes Trusted advisor with strong judgment and discretion Calm, decisive, and highly credible with senior executives Structured thinker who simplifies complexity Comfortable holding leaders accountable while maintaining strong relationships Bias for action with a relentless focus on outcomes Compensation The base range for this position is $200,000 to $220,000, on a full-time schedule. Along with base compensation, Trupanion employees are currently eligible for monthly bonuses. We want all employees to be invested in Trupanion’s success, so we grant Restricted Stock Units to all new team members. Our new hire grants vest over 4 years. Benefits and Perks: Full medical, dental, and vision benefits at no cost to the employee Four weeks of paid time off and 9 paid float holidays (you can decide which days are most important to you!) Five-week sabbatical after five years of employment Open, casual, pet-friendly, and fun office environment Free medical health insurance for your pet (1 dog or cat) Paid time off to volunteer at nonprofit organizations Seattle Office Amenities: Free on-site gym, free dog walking services for office pets during business hours, free parking, and paid ORCA cards. For more information about Trupanion, visit https://trupanion.com/about Learn more about how Trupanion has revolutionized our industry and the reimbursement model: https://www.youtube.com/watch?v=vdWZ4KHiPTQ Trupanion is an equal-opportunity employer and embraces diversity. We are committed to building a team that represents a variety of backgrounds, abilities, perspectives, and skills. We will ensure that individuals are provided reasonable accommodation to participate in the job application or interview process, perform essential job functions, and receive other benefits and privileges of employment. Please contact us to request accommodations.