Director of IS & AI

OBM is hiring a Senior IT leader to run our Information Systems function as the company grows. You'll manage the IT team day to day while also owning the longer-term view: where our technology and systems need to be in two, three, and five years, not just today. A core part of this role is leading AI adoption across OBM — setting usage guidelines, training employees at every level to use AI tools effectively and responsibly, and evaluating which tools are worth adopting. You'll also own visibility into external systems OBM relies on, understanding what we're paying for, where there's overlap or redundancy, and where consolidation or change makes sense.

Key Responsibilities

IT Leadership & Team Management

• Manage, mentor, and grow the Information Systems team, setting priorities and performance expectations — this role's scope extends beyond core IT to other functional specialists who report into Information Systems.

• Own IT operations and support across all OBM offices, ensuring reliable systems and fast issue resolution.

Long-Term IT Strategy

• Build and maintain a multi-year IT roadmap that anticipates OBM's growth — new markets, new offices, and evolving business needs.

• Define the future-state technology architecture and present strategic recommendations to leadership.

• Own the IT budget, balancing near-term needs against long-term investment.

AI Adoption & Training

• Set company-wide guidelines and best practices for responsible, effective AI use.

• Design and deliver training so employees across departments — not just IT — can use AI tools confidently and appropriately.

• Evaluate emerging AI tools and platforms, and lead rollout of the ones worth adopting.

• Track and report on AI adoption and impact across the company.

Systems & Vendor Portfolio Management

• Maintain a current inventory of external systems and software vendors used across OBM.

• Identify overlap, redundancy, or underused tools, and recommend consolidation or changes.

• Own vendor relationships, contract renewals, and renegotiations.

• Partner with department leaders to understand their tooling needs and evaluate new system requests.

• Source and evaluate new tools and software as needs arise across the company, and lead training so teams can adopt them effectively — not limited to AI tools.

Security & Continuity

• Oversee OBM's IT security posture, including data protection practices and access controls.

• Own business continuity and disaster recovery planning for critical systems.

What You'll Bring

• 10+ years of progressive IT experience, including experience leading and managing a team.

• A track record of building and executing on an IT strategy or roadmap at a growing or multi-location company.

• Direct experience evaluating and rolling out AI tools in a business setting — you don't need to be an AI researcher, but you understand what's genuinely useful versus hype, and how to get an organization to actually use new tools.

• Experience managing a portfolio of external systems and vendors, including contract negotiation and renewal.

• Strong training and communication skills — you can make technical and AI concepts clear and actionable for non-technical employees.

• Solid grounding in IT security fundamentals and business continuity planning.

• Bachelor's degree in Information Technology, Computer Science, Business, or a related field, or equivalent experience.

Nice to Have

• Experience in advertising, media, or another multi-location services industry. 

• Experience developing a formal AI governance or acceptable-use policy.

• Background in organizational change management, given the training and adoption component of this role.

• Experience presenting technology strategy and recommendations directly to senior leadership.