Director, Information Technology

About Learning Without Tears (LWT)

At Learning Without Tears, we're more than just a company; we're a passionate, family-owned community on a mission to revolutionize education. We believe that learning should be engaging and joyful, which is why we create innovative, fun products and digital resources that empower educators and inspire children.

Every day, our commitment to collaboration and creativity propels us forward. We're dedicated to embracing change, striving for excellence, and simplifying processes to create a lasting impact in the lives of educators and learners alike.

Join our dynamic team and be a part of something truly transformative as we shape the future of education together!

• 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
• 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:
  • Net Suite (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 Net Suite, 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 (Net Suite,…