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Agent guide: [/agents.md](https://www.wearedevelopers.com/agents.md). --- # Director, Information Technology - **Company:** Learning Without Tears - **Location:** Gaithersburg, MD, United States - **Experience:** Expert - **Salary:** $160,000.0 - $180,000.0 - **Contract:** Permanent contract - **Skills:** Artificial Intelligence, Amazon Web Services, Microsoft Azure, Business Systems, Software as a Service, Cloud Computing, Cyber Security, Disaster Recovery, Identity and Access Management, Automation of Marketing, Netsuite, Salesforce.Com, Data Streaming, System Availability, Reliability of Systems, Information Technology - **Published:** May 31, 2026 - **Apply:** https://www.indeed.com/viewjob?jk=dedf95469a8cf4db ## About the Role Do you have experience in Technology management?, * 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 Core Competencies * 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 Preferred * 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) Success Metrics * High-performing, engaged IT team with strong accountability and execution * Effective partnership and trust with the Senior Leadership Team * Measurable progress integrating AI and automation into business workflows * High system reliability, security, and user satisfaction * Strong adoption and optimization of NetSuite, Salesforce, and UKG * Technology investments delivering clear business value ## Description * 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 Executive Partnership & Communication * 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 IT Strategy & Operations * 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 Infrastructure & Cloud Operations * 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 Enterprise Business Systems Ownership * 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 AI, Automation & Data Enablement * 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 Cybersecurity & Risk Management * 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 Technical Support & Employee Experience * 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) Vendor & Partner Management * 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 ## 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