Senior Director, IT & Enterprise Applications - 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 Role

The Senior Director, Information Technology & Business Applications is responsible for the strategic leadership, operational excellence, and continuous evolution of CentralSquare's internal technology organization. This role oversees Corporate IT, Enterprise Infrastructure, Service Delivery, Business Applications, and Technology Enablement functions while ensuring technology investments, platforms, and services effectively support business objectives and company growth.

As a key technology leader, the Senior Director will develop and execute technology strategy, lead high-performing teams, manage budgets and vendor relationships, drive enterprise systems and operational improvements, and partner with executive leadership to deliver secure, scalable, and innovative technology solutions. The role serves as IT's representative on the AI Innovation Committee and is accountable for advancing the company's AI-first strategy through responsible adoption, governance, and enablement.

Key Responsibilities:

AI Strategy & Enablement

• Craft and drive the vision and roadmap for internal systems and business applications that is AI-first, and communicate it across the IT organization and to key stakeholders.

• Represent IT on the AI Innovation Committee and 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), and enable security mandates across Platform & MCP/Integrations within established timelines.

• 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.

Strategic Leadership

• Develop and execute the vision, strategy, and roadmap for Corporate IT and Business Applications aligned with business objectives.

• Partner with executive leadership to identify and implement technology solutions that improve operational efficiency, employee productivity, and business outcomes.

• Establish governance frameworks, performance metrics, and reporting mechanisms to measure operational and strategic success.

• Evaluate emerging technologies and drive innovation while balancing risk, cost, and organizational priorities.

Organizational Leadership

• Lead, mentor, and develop managers and team members across IT and Business Applications functions.

• Build a high-performing, customer-focused organization through talent development, succession planning, and organizational design.

• Foster a culture of accountability, collaboration, continuous improvement, and service excellence.

• Align teams and resources to strategic priorities and business needs.

IT Operations & Business Applications

• Provide leadership and oversight for enterprise infrastructure, end-user technology, service desk operations, business applications, integrations, and technology support services.

• Ensure reliability, availability, scalability, and performance of all internal technology platforms and services.

• Establish and maintain service delivery standards and operational performance metrics.

• Lead prioritization, governance, and execution of technology projects and enhancement initiatives.

• Oversee enterprise application strategy, implementation, optimization, and lifecycle management.

Financial & Vendor Management

• Manage and support strategic vendor relationships, contract negotiations, licensing agreements, and technology procurement.

• Drive effective resource allocation and cost optimization while supporting innovation and growth.

• Ensure technology investments deliver measurable business value and operational effectiveness.

Security, Compliance & Governance

• Partner with our CISO to maintain compliance with company policies, regulatory requirements, and CJIS standards.

• Support risk management, business continuity, disaster recovery, and data governance initiatives.

• Ensure technology solutions are deployed and managed in accordance with security and compliance requirements.

Requirements

• Bachelor's degree in Information Technology, Computer Science, Business, Engineering, or a related field, or equivalent experience.

• 10+ years of progressive IT leadership experience, including 5+ years leading multiple technology functions. Experience leading direct and indirect reports of up to 30+ employees across multiple disciplines.

• Demonstrated experience evaluating, implementing, and driving adoption of AI and automation technologies to improve business outcomes. Already using AI tools (preferably Claude) in daily workflow.

• Familiarity with CJIS requirements, compliance frameworks, and enterprise security governance.

• Proven success leading enterprise IT organizations that include infrastructure, business applications, service delivery, and technology operations.

• Experience developing and executing technology strategy, roadmaps, and multi-year investment plans. Demonstrated success leading organizational transformation and enterprise technology initiatives.

• Strong cross-functional communicator and stakeholder management skills. Comfortable partnering with security, legal, and other internal stakeholders

• Strong project portfolio management across multiple concurrent workstreams with the proven ability to balance strategic planning with operational execution and accountability.

Preferred Qualifications

• Experience in SaaS, software, public sector technology, or other highly regulated environments.

• Advanced degree and/or multiple relevant industry certifications.