Director of IT

Who We Are

Goodway Group is one of AdAge's 2026's BEST PLACES TO WORK!  As an independent and remote-first media and marketing services firm with a 90+ year history, Goodway Group has the security of an established company combined  with a start-up feel.  With leading data-driven and technology-enabled digital media and marketing services firm with teams in the U.S. and the UK, our diverse team of digital strategists, media practitioners, technologists and data scientists have won the most prestigious awards for innovative marketing technology, impactful work and inclusive remote-first places to work including being honored as a multiyear winner in Ad Age Best Places to Work, Ad Exchanger's Best Use of Technology by an Agency Award and two MarTech Breakthrough Awards and a certified service partner to The Trade Desk.

Goodway is seeking a forward-thinking Director of IT to lead a modern, AI-enabled technology function that drives efficiency, scalability, and business impact. Reporting to the CFO, this role connects 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/Collaborate with the CFO, Leadership, and all parts of the organization 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 and maximize business benefits of the projects 
• Team Leadership & Operations - Lead and develop a hybrid IT support model (internal team + external helpdesk) with clear roles, SLAs, and accountability, Ensure the team is properly staffed, balanced, and cross-trained to reduce and eliminate single points of failure.  Foster a culture of ownership, responsiveness, and continuous improvement 
• Infrastructure, Security & Vendors  - Conduct formal risk assessments. Manage SOC2 and other compliance and audit initiatives to ensure that we are compliant with letter and spirit of requirements on an ongoing basis. 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.  Implement modern security and governance practices, including AI-related risks.  Conduct formal risk assessments. Manage SOC2 and other compliance and audit initiatives to ensure that we are compliant with letter and spirit of requirements on an ongoing basis. 
• AI, Automation & Data Enablement  - Drive practical adoption of AI and automation to streamline workflows and enhance decision-making.  Champion a data-first approach, improving system integration, data quality, and accessibility. Stay out ahead of industry trends, best practices, security and innovation in the IT space, prioritizing and infusing these into the Goodway IT function & road map as appropriate.  
• Adoption & Change Management  -  Drive adoption of new tools and workflows across the organization.  Enable teams through training and support, particularly in AI-enabled tools and automation 

What You Bring

• 10+ years of IT leadership experience, including managing infrastructure, vendors, and support teams 
• Experience operating within or closely with Finance, Legal, HR, and Operations; strong business and cost-management mindset 
• Demonstrated success leading transformation initiatives (cloud, automation, or data platforms) 
• Working knowledge of AI/automation tools and their practical business applications 
• Proven ability to lead distributed teams and third-party partners effectively 
• Strong communicator with a pragmatic, outcomes-driven approach 

Success Measures 

• Improved operational efficiency through automation and AI adoption 
• High-performing, cross-trained IT team with strong service levels 
• Reliable, secure systems with minimal disruption 
• Clear ROI and optimization of IT spend 
• Strong adoption of tools that improve employee productivity 

Check us out at www.goodwaygroup.com to learn more!

If you identify as a female candidate, and feel you can do this role even if there are a few things perhaps you've not done, please apply anyway!  Goodway Group is 70% Female!  We realize that men tend to apply for jobs when they can meet around 60% of the requirements for the role, where women tend to only apply when they know they meet 100% of the requirements.  

Goodway Group is human-first, constantly working to become more inclusive and to make sure our employee population reflects our desire to constantly add to our diversity in all ways.  We want applications from everyone, regardless of race, creed, color, religion, sex, sexual orientation, gender identity, national origin, marital status, citizen status, age, disability, military or protected veteran status, genetic predisposition or carrier status or any other legally protected status.