AI Organizational Change Manager - 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.

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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.

While this role will support change efforts across all enterprise initiatives, AI adoption is the explicit primary focus. The OCM will use structured organizational change management (OCM) methodology as the mechanism — stakeholder engagement, resistance management, communications, and leader coaching — to drive measurable adoption of AI tools and workflows throughout CentralSquare.

This role sits within the Enterprise PMO under the Director of Business Operations and partners closely with the VP of Business Operations on strategy, executive coaching, and change leadership.

Change Management Strategy

•    Design and execute OCM strategies for enterprise transformation initiatives, with AI adoption as the primary focus.

•    Assess organizational change readiness and change impact across affected functions and teams.

•    Develop stakeholder engagement plans that build understanding, commitment, and adoption at all levels of the organization.

•    Identify and manage resistance — understand its source, surface it to the right leaders, and build mitigation strategies.

AI Adoption & Enablement

•    Lead adoption planning for AI tool rollouts — ensuring that new AI capabilities are actually used, not just deployed.

•    Partner with initiative owners to design user enablement programs: training, communications, and job aids that drive behavior change.

•    Track adoption metrics for AI tools and programs, including usage rates, proficiency indicators, and self-reported confidence.

•    Build feedback loops that surface adoption barriers early and inform continuous improvement.

Leader Coaching & Capability Building

•    Coach initiative leaders and people managers on change leadership — helping them model new behaviors, communicate the why, and support their teams through transitions.

•    Partner with the VP of Business Operations to identify leaders who need change management coaching and deliver it directly or through structured support.

•    Build organizational capability to manage change effectively over time, not just for individual initiatives.

Communications & Engagement

•    Develop change communications that are clear, timely, and tailored to the audience — from frontline agents to senior leaders.

•    Ensure ELT and initiative sponsors are active, visible champions of transformation efforts.

•    Facilitate large-scale change meetings and working sessions when a team or department is navigating an AI transition — for example, supporting a function like Customer Support through a full AI tool adoption process, from announcement through go-live.

Measurement & Reporting

•    Define change success metrics and track them throughout the life of each initiative.

•    Report change health and adoption progress to the VP of Business Operations and ELT.

Requirements:

•    5+ years of organizational change management experience, including direct ownership of enterprise-scale transformation programs.

•    Demonstrated experience driving adoption of technology platforms — AI, SaaS, or similar — within complex organizations.

•    Proficiency in structured OCM methodologies (Prosci/ADKAR, Kotter, or equivalent).

•    Strong coaching and facilitation skills; able to influence leaders without direct authority.

•    Excellent written and verbal communication skills, including executive-level communication.

•    Comfortable operating in ambiguity and building change infrastructure from scratch.

•    Familiarity with AI tool adoption and the specific organizational resistance patterns that accompany it.

•    Prosci ADKAR or CCMP certification.

•    Background in public safety, public administration, or government software is a plus.