Lead Project Manager (AI Initiatives) - Remote

CentralSquare Technologies builds technology that supports public servants and communities across North America. The Lead Project Manager of AI Initiatives will govern and coordinate the company’s AI program portfolio, translating strategic objectives into executable plans, tracking risks and outcomes, and preparing executive-level reporting. The role will collaborate across Product, Engineering, Customer Support, Managed Services, the Enterprise PMO, and executive stakeholders.

Responsibilities:

• Maintain a current inventory of all active AI initiatives across the enterprise, including ownership, status, milestones, and KPIs
• Establish and run a consistent governance cadence for AI programs: weekly check-ins, milestone reviews, and escalation processes
• Track initiative health and surface risks, blockers, and dependencies before they become delivery failures
• Ensure AI initiative owners have clear charters, defined success criteria, and accountability structures in place
• Partner with AI initiative owners to build out project plans, timelines, and resource maps for new and in-flight programs
• Translate high-level AI strategy objectives into executable work plans with clear owners, dates, and deliverables
• Facilitate planning sessions, working sessions, and retrospectives across AI workstreams
• Identify and resolve cross-initiative dependencies and conflicts within the AI portfolio
• Produce 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 impact
• Maintain dashboards that track AI initiative progress, adoption metrics, and outcome KPIs including deflection rates, CSAT, and agent productivity gains
• Prepare briefing materials for Vista Value Creation Team updates and executive steering reviews
• Act as the connective tissue between AI initiative owners, the Enterprise PMO, and the VP of Business Operations
• Coordinate across Product, Engineering, Customer Support, Managed Services, and other functions to ensure AI programs have the cross-functional alignment they need to execute
• Support the AI Council cadence: prepare agendas, capture decisions and action items, and track follow-through

Requirements:

• 5+ years of project management experience, including direct ownership of complex, cross-functional programs
• Demonstrated experience managing technology or software implementation programs
• Strong command of project governance frameworks: charter development, milestone tracking, risk management, and escalation
• Exceptional communication skills; able to translate technical AI program details into clear executive-level reporting
• Proficiency with project and portfolio management tools (Azure DevOps, Smartsheet, or similar)
• Comfortable operating in ambiguity and building structure where it does not yet exist
• Familiarity with AI tooling ecosystems including generative AI platforms, LLM-based tools, and AI vendor landscapes
• AI, SaaS, or platform projects preferred
• PMP, PMI-ACP, PRINCE2
• Background in public safety, public administration, or government software