Lead Project Manager (AI Initiatives) - Remote

What We're About

At CentralSquare, we don't just build software - we power public servants and uplift communities with Hero-Grade Technology. Every line of code, every feature we deliver helps heroes across North America protect, serve, and save lives. When you join us, you become part of a mission-driven team creating technology that makes communities safer and stronger.

Your Growth Matters. We believe heroes deserve opportunities to rise. That's why we invest in your career with mentorship, learning programs, and clear paths for advancement. If you're motivated, there's no limit to how far you can go.

Your Commitment Deserves Reward. We offer competitive compensation and a benefits package designed to support your life inside and outside of work-tuition reimbursement, parental leave, paid volunteer hours, and unlimited PTO. Plus, our flexible work environment gives you the freedom to balance your heroic work with personal well-being, whether you're in the office or remote.

Join us and help build the tools that power real-life heroes. Together, we make a difference.

The Opportunity

CentralSquare Technologies is hiring a Lead Project Manager of AI Initiatives to serve as the dedicated project management resource for the company''s growing portfolio of AI programs. As CentralSquare accelerates its AI-first transformation (spanning customer support AI, managed service innovation, and enterprise-wide AI adoption), this role provides the operational discipline, tracking rigor, and cross-functional coordination required to move initiatives from concept to measurable outcome.

This role sits within the Enterprise PMO under the Director of Business Operations and partners closely with the VP of Business Operations, who leads enterprise AI strategy. The Lead PM will not own AI strategy but will ensure that AI initiatives are governed, tracked, and reported with the same discipline applied to all strategic programs across the portfolio.

Key Responsibilities

AI Initiative Governance

• 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.

Planning & Execution Support

• 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.

Reporting & Executive Visibility

• 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.

Stakeholder Coordination

• 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.