Vice President, IT Project Management Office

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 partnerensuring 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 

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

Qualifications :

Required

• 15 years of experience in technology delivery program management or enterprise transformation
• 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

Additional Information :

Compensation

• The pay range for this position is $200000 to $220000 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 Trupanions 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 more about how Trupanion has revolutionized our industry and the reimbursement model: 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.

Remote Work :

No

Employment Type :

Full-time