IT Portfolio Manager

Say hello to Hagerty Hagerty is a company built by drivers for drivers. We put our members at the center of everything we do and are dedicated to making it easier and more enjoyable for enthusiasts to drive and celebrate the machines they love. We’re proud to be the world’s largest insurer of collectible and enthusiast vehicles and are home to the Hagerty Drivers Club, the world’s largest car club. Our Marketplace business presents live and digital sales across the U.S. and Europe, we host a number of driving events and concours, and our award-winning automotive journalists produce the most popular car magazine globally, alongside internationally awarded videos. We’re committed to Never Stop Driving. Ready to get in the driver’s seat? Join us! As an IT Portfolio Manager , you will play a critical role in overseeing and optimizing the delivery of a defined portfolio of technology initiatives aligned to a specific value stream or domain. This role partners closely with Senior Engineering, Architecture, Product and Business Leaders to optimize the flow of value, ensure alignment to strategic objectives, and enable predictable, high-quality delivery across multiple, interdependent teams. The IT Portfolio Manager bridges team-level agility and program-level coordination, providing structure, visibility, and governance while fostering collaboration and continuous improvement. This role requires strong systems thinking, delivery leadership, and the ability to influence across organizational boundaries. What you’ll do Portfolio Strategy & Alignment Establish, lead, and continuously improve portfolio-level delivery and governance processes within an assigned domain or value stream. Implement and mature portfolio management practices including prioritization, visualization, dependency management, constraint identification, capacity planning, and risk mitigation. Ensure portfolio initiatives align to organizational strategy, business outcomes, and value delivery goals. Delivery Orchestration & Flow Optimization Orchestrate delivery across multiple teams and initiatives, including Epic-level coordination as needed. Partner with Engineering Leaders, Value Stream Business Owners, Module Owners, Business Leads, Technical Product Managers and Scrum Masters to plan, sequence, and execute work effectively. Identify and manage cross-team dependencies to reduce friction, rework and delivery risk. Bridge team-level execution with program-level milestones and business value delivery. Coaching & Ways of Working Promote delivery best practices, including Scrum ceremonies, readiness standards, Agile accounting practices, and Azure DevOps (ADO) hygiene. Support experimentation and continuous improvement to optimize delivery effectiveness and communication. Foster mature collaboration between technical teams and across a complex, interdependent ecosystem. Metrics, Visibility & Communication Partner with senior leadership to define and evolve metrics that measure portfolio health, delivery effectiveness, and value realization. Measure, monitor, and mature delivery metrics at the value stream level. Provide clear, timely communication of portfolio status, risks, dependencies, and outcomes to senior leadership and stakeholders. Ensure transparency into delivery progress through dashboards, visualizations, and structured ceremonies. Key Work Products Portfolio and Program Delivery Plans with technical critical path milestones and business value milestones Risk identification and mitigation plans Program-level planning, status, and governance ceremonies and artifacts Go-live and operational readiness plans in partnership with Engineering and Product leaders Cross-team dependency visualizations and work item tracking Value stream dashboards and delivery metrics Quarterly planning artifacts for the value stream Retrospective insights, improvement experiments, and delivery maturity initiatives How This Role Fits in the Ecosystem IT Portfolio Managers orchestrate the work that is prioritized and how value flows. This role focuses on how delivery is enabled, with support from Scrum Masters that are effective leaders, facilitators, and change agents within value streams. Together, these roles create a balanced system of delivery orchestration and delivery This might describe you Strong leadership, facilitation, and stakeholder influence skills Deep understanding of IT program and project management principles Practical expertise with Scrum and Agile delivery practices Systems thinking and the ability to manage complex, interdependent work Excellent communication skills across technical and non-technical audiences Experience working with senior engineering and executive leadership Ability to balance structure with adaptability in a dynamic environment Other things to note This position is open to U.S. remote work. However, team members who reside within 20 miles of the Traverse City headquarters will follow a hybrid schedule, working from the office three days per week. May require travel for quarterly events. Familiarity with public company requirements, including Sarbanes Oxley and key regulations, if applicable. For SOX compliant roles, responsible for designing, executing, and documenting internal controls where they have been identified as owners to prevent errors in financial reporting, processes, and business operations. Including attestation to the completeness, accuracy, and compliance of all financial reporting data, where applicable. If you reside in the following jurisdictions: Illinois, Colorado, California, District of Columbia, Hawaii, Maryland, Minnesota, Nevada, New York, or Jersey City, New Jersey, Cincinnati or Toledo, Ohio, Rhode Island, Washington, British Columbia, Canada please email [email protected] for compensation, comprehensive benefits and the perks that set us apart. At Hagerty, we share the road. We are an inclusive automotive community where all are welcomed, valued and belong regardless of race, gender, age, or car preference.  We are united by our shared passion for driving, our commitment to preserve car culture for future generations and our desire to make a positive impact in the world. #LI-Remote / #LI-Hybrid / #LI-Onsite EEO/AA US Benefits Overview Canada Benefits Overview UK Benefits Overview If you like wild growth and working with happy, enthusiastic over-achievers, you'll enjoy your career with us!