The District’s web. team manages a portfolio of concurrent initiatives across more than 100 agency websites. The largest is the dc.gov redesign, which itself comprises multiple sub-projects including design implementation, content migration, agency-wide launch, and integration of AI—powered search. OCTO requires an experienced Master Program Manager who can bring structure, visibility, and accountability across this full portfolio, ensure each sub-project has a defined scope and milestone plan, and give OCTO leadership a clear, current picture of status across all active work. Key Duties: Establish and maintain a portfolio-wide tracking system (RAID log, milestone schedules, dashboard) covering all active web team projects. Run a recurring status reporting cadence to OCTO leadership across the full portfolio Partner with OCTO SMEs to define project requirements and scope, including for initiatives that may require external vendor support Advise on vendor/contractor scoping and deliverables, drawing on familiarity with SOW structure and government IT procurement norms Track risks, issues, dependencies and action items across projects, escalating to OCTO leadership as needed Report on project status, milestones, and delivery readiness across the portfolio, with the dc.gov relaunch as the flagship initiative Minimum Qualifications: Demonstrated ability to translate technical and business requirements into actional project scope, working directly with subject matter experts Experience supporting or informing scope of work development for external vendor contracts (SOWs, deliverables, acceptance criteria) Experience managing a multi-project portfolio simultaneously, including establishing. PM tooling, reporting cadence, and prioritization across competing initiatives Bachelor's degree in a related field, or equivalent experience 11 years of program/project management experience, including large-scale website or CMS transition and migration projects Experience managing multi-stakeholder government or enterprise projects Working knowledge of Drupal CMS and website content migration practices PMP certification preferred Familiarity with AI/ML project delivery timelines and dependencies a plus, given active AI integration work within the portfolio Strong communication, organizational, and stakeholder management skills Prior experience supporting DC government or comparable public-sector clients preferred