Director of IT

About Goodway Group

Goodway Group is one of AdAge's 2025 Best Places to Work and a leading, independent remote-first media and marketing services firm with a 90+ year history. We combine the security and resources of an established organization with the agility and innovation of a startup. With teams across the U.S. and UK, our diverse workforce of digital strategists, media practitioners, technologists, and data scientists has earned prestigious recognition including multiple Ad Age Best Places to Work awards, Ad Exchanger's Best Use of Technology by an Agency Award, two MarTech Breakthrough Awards, and certified service partner status with The Trade Desk.

The Role

We're seeking a forward-thinking Director of IT to lead a modern, AI-enabled technology function that drives efficiency, scalability, and measurable business impact. Reporting to the CFO, you'll connect IT strategy with overall company objectives—leveraging automation, data, and AI to improve operations and decision-making across the organization. This leader will oversee both an internal IT team and an external helpdesk partner, ensuring seamless support, strong accountability, and a high-performing, well-balanced team.

What You Will Do

• Strategic & Financial Alignment – Partner with the CFO, leadership, and all departments to align IT strategy, budgets, and investments with business goals and ROI. Identify opportunities to improve efficiency through automation and smarter tooling. Minimize business disruption while maximizing business benefits of technology initiatives.
• Team Leadership & Operations – Lead and develop a hybrid IT support model combining internal team and external helpdesk resources with clear roles, SLAs, and accountability measures. Ensure the team is properly staffed, balanced, and cross-trained to eliminate single points of failure. Foster a culture of ownership, responsiveness, and continuous improvement across all IT functions.
• Infrastructure, Security & Vendor Management – Oversee secure, reliable, and scalable IT systems, including cloud platforms and enterprise tools. Manage vendor relationships and optimize the technology stack for performance and cost-effectiveness. Implement modern security and governance practices, including AI-related risk mitigation. Conduct formal risk assessments and manage SOC2 and other compliance and audit initiatives to ensure adherence to both letter and spirit of requirements on an ongoing basis.
• Technology Stack Modernization – Lead the evaluation and implementation of emerging technologies that enhance organizational capability. Ensure infrastructure supports remote-first operations and integrates AI-enabled solutions that drive efficiency gains across business functions.
• Stakeholder Communication – Translate technical concepts for executive and non-technical audiences. Provide regular updates on IT health, security posture, and strategic initiatives to leadership and board-level stakeholders.

What You Bring

• Proven experience leading IT teams and managing hybrid internal/external support models
• Strong background in IT strategy, infrastructure management, and enterprise technology platforms
• Deep knowledge of cloud technologies, cybersecurity best practices, and compliance frameworks (SOC2, etc.)
• Experience with vendor management and technology stack optimization
• Understanding of AI applications in business operations and associated governance/risk considerations
• Excellent leadership skills with ability to build and develop high-performing teams
• Strong financial acumen and ability to align IT investments with business ROI
• Experience in remote-first or distributed organization environments
• Track record of driving operational efficiency through technology enablement

Why Join Goodway Group

This is an exceptional opportunity to shape the future of IT at a thriving, award-winning organization with genuine commitment to remote-first culture and employee development. You'll work directly with C-suite leadership to influence strategic direction, lead modern technology initiatives, and build a best-in-class IT function. Our remote-first structure provides flexibility and autonomy while maintaining the collaborative culture and resources of an established firm.

💰 Compensation not publicly listed. Market estimate for similar roles: from $200K, varying by experience and location.