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! What You’ll Be Doing: IT Leadership & Team Development 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 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 Your Experience & Qualifications: 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 Why Work with Us? Mission-Driven Impact: Join a team passionate about making a difference and driving positive change. Growth and Development: We invest in your success with ongoing learning and career opportunities. Work-Life Balance: Enjoy flexible work options, generous PTO, and wellness support. Inclusive Culture: We foster a diverse, collaborative, and supportive workplace. Competitive Benefits: Receive competitive pay, comprehensive benefits, and employee recognition. Apply now at Learning Without Tears is an Equal Opportunity and Aff... Employer. #J-18808-Ljbffr Learning Without Tears