Vice President, IT Project Management Office

Company DescriptionTrupanion 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.

Job DescriptionThe 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 ResponsibilitiesEnterprise IT PMO LeadershipBuild, lead, and mature a best-in-class IT PMO supporting global, cross-functional initiativesEstablish 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 CIOPartner closely with the CIO to translate technology vision, strategy, and priorities into executable roadmapsSupport CIO operating cadence: leadership meetings, executive reviews, steering committees, and strategic planning sessionsDrive alignment across CIO direct reports and proactively resolve cross-team dependencies and execution risksTrack and follow through on enterprise commitments, decisions, risks, and outcomesPortfolio, Financial & Value ManagementOwn enterprise IT portfolio management, including intake, prioritization, sequencing, capacity planning, and dependency managementPartner with Finance to manage IT investment governance, budgets, forecasts, and ROI trackingEstablish clear metrics tied to business outcomes (delivery predictability, cost optimization, value realization, risk reduction)Executive & Board EngagementPrepare executive-level communications, dashboards, and materials for ELT, Board, and Audit/Risk CommitteesEnsure technology initiatives are communicated in business terms (outcomes, value, risk, tradeoffs)Support CIO in board, investor, and regulatory communications as neededGovernance, Risk & AccountabilityEstablish governance models that balance speed with appropriate controlsProactively identify delivery risks, execution gaps, and organizational bottlenecksDrive clear accountability while fostering a culture of trust, ownership, and continuous improvementLeadership & Talent DevelopmentBuild and lead a high-performing PMO organization with strong program, portfolio, and delivery leadersCoach senior leaders on execution discipline, decision-making, and delivery rigorServe as a role model for executive presence, communication, and cross-functional collaborationQualificationsRequired15+ years of experience in technology delivery, program management, or enterprise transformationBachelor's degree in Business Administration, Management Information Systems (MIS), or related technical fieldPrior experience leading an enterprise or global PMOProven track record partnering directly with C-suite executives, including CIOs Experience managing complex, multi-year technology programs with material financial and operational impactStrong financial acumen (budgeting, forecasting, ROI)Exceptional executive communication and stakeholder management skills3+ years experience in JIRAPreferredExperience in regulated or complex environments (public company, SOX, PCI, HIPAA, etc.)Broad technology exposure across applications, infrastructure, data, and securityMBA or advanced degreeLeadership AttributesTrusted advisor with strong judgment and discretionCalm, decisive, and highly credible with senior executivesStructured thinker who simplifies complexityComfortable holding leaders accountable while maintaining strong relationshipsBias for action with a relentless focus on outcomesAdditional InformationCompensationThe base 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.

Benefits and Perks:

Full medical, dental, and vision benefits at no cost to the employeeFour 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 employmentOpen, casual, pet-friendly, and fun office environmentFree 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/aboutLearn more about how Trupanion has revolutionized our industry and the reimbursement model: https://www.youtube.com/watch?v=vdWZ4KHiPTQTrupanion 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.