Vice President, IT Project Management Office

Vice President, IT Project Management Office

• Full-time
• Department:
  Information Technology
• Compensation: USD 200,000 - USD 220,000 - yearly

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.

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.

• 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

• 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
• Own enterprise IT portfolio management, includingintake,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)

• 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
• 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

• 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

• 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

• Experience in regulated or complex…