Senior Project Manager

Role Description

CentralSquare Technologies is hiring a Senior Project Manager of AI Initiatives to serve as the dedicated project management resource for the company's growing portfolio of AI programs. This role provides the operational discipline, tracking rigor, and cross-functional coordination required to move initiatives from concept to measurable outcome.

• 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.
• Maintain dashboards that track AI initiative progress, adoption metrics, and outcome KPIs.
• 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.

Qualifications

• 5+ years of project management experience, including direct ownership of complex, cross-functional programs.
• Demonstrated experience managing technology or software implementation programs — AI, SaaS, or platform projects preferred.
• 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.
• PMP, PMI-ACP, PRINCE2.
• Background in public safety, public administration, or government software is a plus.

Benefits

• Competitive compensation.
• Benefits package designed to support your life inside and outside of work.
• Tuition reimbursement.
• Parental leave.
• Paid volunteer hours.
• Unlimited PTO.
• Flexible work environment.