The Role This role will lead CentralSquare's internal IT organization through its AI-first transformation. In addition to overseeing all IT domains, this role represents IT on the AI Innovation Committee, the cross-functional group where every function sends a representative to coordinate AI adoption company-wide. Internal IT is the enablement backbone that makes AI possible for every other function: this role owns the platform, playbook, and people that make that true.
Key Responsibilities:
- Craft and drive the vision and roadmap for internal systems that is AI-first, and communicate it across the IT organization and to key stakeholders
- Develop mechanisms to track progress against that roadmap
- Represent IT on the AI Innovation Committee; coordinate cross-functional AI enablement needs alongside representatives from every other function
- Establish and run an AI-first prioritization process for IT: define an intake process for IT projects, run a regular cadence to prioritize and commit to system changes, and report out on progress
- Own the AI tool deployment playbook: meet roadmap timeline goals from approval to live for any new AI tool
- Hold accountability for 99.9% uptime across all AI platforms (Claude, Agentforce, Forethought, LinearB, Innovation Lab, future tools)
- Drive the 5-domain AI org structure within IT: AI Platform & Security, AI Data & Integrations, AI-Powered Applications, AI-First IT Support, AI Ops
- Partner with the CISO on governance around data and integration use, including MCP governance
- Champion Claude adoption across the company, from 144 users to org-wide saturation, as part of IT's role as the AI enablement backbone
- Report IT AI metrics monthly: platform uptime, helpdesk deflection rate, AI tool deployment velocity
- Own IT budget allocation and accountability to expense goals with an AI-first lens; prioritize Accelerator and Enabler tier initiatives
- Partner with Infrastructure Team to build and maintain a CJIS-compliant AI governance framework
- Partner with the CISO to enable security mandates across Platform & MCP/Integrations within established timelines
AI Success Metrics:
- 99.9% AI platform uptime (Claude, Agentforce, Forethought, etc.)
- New AI tool deployment SLA: meet roadmap timeline goals from approval to live
- 40% IT helpdesk tier-1 deflection via AI by end of 2026
- 100% of AI Accelerator tasks in active progress by Q2 2026
Skills & Requirements
Requirements - 5+ years IT leadership experience, including demonstrated experience owning and transforming an IT team
- Demonstrated AI adoption: already using Claude and AI tools in daily workflow
- Strong cross-functional communicator, comfortable partnering with security, legal, and other internal stakeholders
- CJIS compliance awareness; public sector IT governance experience a plus
- Strong project portfolio management across multiple concurrent workstreams
Additional Considerations:
- Bachelors Degree in Information Technology (or similar), or equivalent experience
- Experience leading both direct and indirect teams of up to 30+ individual contributors
Qualifications
