Director, Information Technology

Learning Without Tears•Gaithersburg, MD

1d•Hybrid

About The Position

The Director of IT is a hands-on, strategic leader responsible for the end-to-end delivery of technology across infrastructure, enterprise systems (NetSuite, Salesforce, UKG), cybersecurity, and technical support for a ~200-person organization. This role leads a team of approximately 8 internal staff, plus managed partners, and requires a balance of operational excellence, strategic vision, and entrepreneurial curiosity. The Director will partner closely with the Senior Leadership Team (SLT) to modernize systems, enable data-driven decision-making, and integrate AI into core business workflows to improve efficiency, insights, and scalability. This role sits at the center of enabling the company's next phase of growth-scaling systems, empowering people, and embedding AI-driven capabilities into everyday work. Success in this position means building a modern, agile IT function that operates as a true business partner-not just a service provider.

Requirements

8+ years of progressive IT experience, including 5+ years of leadership in a mid-sized or high-growth organization
Experience leading multi-functional teams (including internal staff and external partners)
Experience with supporting enterprise platforms such as NetSuite, Salesforce, UKG (or similar)
Strong experience in cloud infrastructure, SaaS environments, and cybersecurity fundamentals
Demonstrated ability to partner with executive leadership and influence business outcomes
Inspirational leadership with the ability to build a driven, accountable, and curious team culture
Strong executive communication skills and comfort engaging with senior leadership
Entrepreneurial mindset-identifies opportunities, moves quickly, and drives results
Collaborative, cross-functional leadership style
Ability to balance strategy and hands-on execution effectively

Nice To Haves

Experience in a 150–300 employee environment
Exposure to AI tools, automation platforms, or analytics initiatives
Experience supporting Finance, HR, and Sales through core systems
Relevant certifications (cloud, cybersecurity, systems)

Responsibilities

Lead, inspire, and develop a high-performing IT organization, fostering a culture of accountability, urgency, and entrepreneurial curiosity
Set clear expectations, priorities, and performance standards that drive a strong work ethic and continuous improvement mindset
Operate as a player-coach, providing both strategic leadership and hands-on execution where needed
Build a team culture focused on service excellence, innovation, and business impact
Serve as the primary IT partner to the Senior Leadership Team (SLT)
Communicate effectively with executives on: Technology strategy and roadmap, System performance and risks, Cybersecurity posture, Investment decisions and ROI
Translate technical concepts into clear business outcomes and actionable insights
Actively contribute to enterprise-wide decision-making, not just IT-specific initiatives
Develop and execute a practical, scalable IT roadmap aligned with company growth and operational priorities
Establish governance, prioritization frameworks, and KPIs appropriate for a mid-sized organization
Ensure reliable, cost-effective delivery across all IT services
Manage IT budget, vendor portfolio, and technology investments
Own cloud infrastructure (AWS/Azure), networks, endpoints, and core SaaS ecosystem
Partner with MSP to ensure high availability, performance, and security
Maintain disaster recovery, business continuity, and system resilience plans
Drive automation and standardization to improve scalability and reduce manual effort
Serve as a partner to the business owners of: NetSuite (ERP/Finance), Salesforce (CRM & revenue operations), UKG (HCM & workforce management)
Ensure systems are optimized to support business workflows, reporting, and decision-making
Lead cross-functional collaboration with Finance, HR, Sales, and Operations
Oversee integrations and data flows to ensure a single, trusted source of truth
Drive user adoption, data quality, and continuous system improvement
Act as a collaborative leader in bringing AI into company workflows, partnering with functional leaders to identify high-impact use cases
Champion practical AI and automation solutions within NetSuite, Salesforce, UKG, and adjacent tools
Enable predictive analytics, workflow automation, and enhanced reporting across the organization
Ensure systems are structured to capture, integrate, and leverage high-quality data
Balance innovation with governance, security, and business value
Establish and maintain a right-sized cybersecurity program leveraging internal leadership and external MSSP capabilities
Ensure foundational controls (MFA, endpoint security, access management, monitoring, backups) are in place
Oversee incident response planning, risk assessments, and compliance efforts
Promote organization-wide security awareness and accountability
Oversee IT support (internal + MSP), ensuring fast, reliable resolution of employee issues
Deliver a high-quality onboarding/offboarding experience
Improve self-service capabilities, knowledge resources, and automation
Track and enhance service metrics (response time, resolution time, user satisfaction)
Manage MSP, MSSP, and provide support for specialized system partners (NetSuite, Salesforce, UKG)
Ensure strong service delivery, accountability, and alignment with business priorities
Optimize vendor footprint for cost, performance, and scalability