Vice President, IT Project Management Office

Company Description

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.

Description

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.

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.

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

• 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, 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)

• 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
• 3+ years experience in JIRA

• 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

• 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

• The pay range for this position is $200,000 to $220,000, on a full-time schedule.
• Along with base salary, Trupanion employees may be 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.

• 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.