[Remote] Senior Project Manager (AI Initiatives) - Remote

Note: The job is a remote job and is open to candidates in USA. CentralSquare Technologies is a trusted provider of public sector software in North America, seeking a Senior Project Manager of AI Initiatives. This role will oversee the governance, planning, and execution of AI programs, ensuring alignment across various functions and reporting on initiative progress.ResponsibilitiesMaintain a current inventory of all active AI initiatives across the enterprise, including ownership, status, milestones, and KPIsEstablish and run a consistent governance cadence for AI programs: weekly check-ins, milestone reviews, and escalation processesTrack initiative health and surface risks, blockers, and dependencies before they become delivery failuresEnsure AI initiative owners have clear charters, defined success criteria, and accountability structures in placePartner with AI initiative owners to build out project plans, timelines, and resource maps for new and in-flight programsTranslate high-level AI strategy objectives into executable work plans with clear owners, dates, and deliverablesFacilitate planning sessions, working sessions, and retrospectives across AI workstreamsIdentify and resolve cross-initiative dependencies and conflicts within the AI portfolioProduce weekly and monthly AI portfolio status reports for the VP of Business Operations and ELT, structured as the AI equivalent of the EPMO portfolio dashboard including initiative health, milestone progress, and ROI indicators such as deflection rates, productivity gains, and cost impactMaintain dashboards that track AI initiative progress, adoption metrics, and outcome KPIs including deflection rates, CSAT, and agent productivity gainsPrepare briefing materials for Vista Value Creation Team updates and executive steering reviewsAct as the connective tissue between AI initiative owners, the Enterprise PMO, and the VP of Business OperationsCoordinate across Product, Engineering, Customer Support, Managed Services, and other functions to ensure AI programs have the cross-functional alignment they need to executeSupport the AI Council cadence: prepare agendas, capture decisions and action items, and track follow-throughSkills5+ years of project management experience, including direct ownership of complex, cross-functional programsDemonstrated experience managing technology or software implementation programs — AI, SaaS, or platform projects preferredStrong command of project governance frameworks: charter development, milestone tracking, risk management, and escalationExceptional communication skills; able to translate technical AI program details into clear executive-level reportingProficiency with project and portfolio management tools (Azure DevOps, Smartsheet, or similar)Comfortable operating in ambiguity and building structure where it does not yet existFamiliarity with AI tooling ecosystems including generative AI platforms, LLM-based tools, and AI vendor landscapesPMP, PMI-ACP, PRINCE2Background in public safety, public administration, or government software is a plusBenefitsMentorship, learning programs, and clear paths for advancementCompetitive compensation and a benefits package designed to support your life inside and outside of work—tuition reimbursement, parental leave, paid volunteer hours, and unlimited PTOFlexible work environment gives you the freedom to balance your heroic work with personal well-being, whether you’re in the office or remoteCompany OverviewCentralSquare Technologies is the trusted provider of public sector software in North America. It was founded in 2018, and is headquartered in Lake Mary, Florida, USA, with a workforce of 1001-5000 employees. Its website is https://www.centralsquare.com/.Company H1B SponsorshipCentralSquare Technologies has a track record of offering H1B sponsorships, with 1 in 2026, 9 in 2025, 5 in 2024, 9 in 2023, 14 in 2022, 7 in 2021, 10 in 2020. Please note that this does not guarantee sponsorship for this specific role.