Director, Innovation

OuterBox is putting AI to work in two places: how our teams deliver marketing services, and the services we sell to clients. The Director of Innovation owns the strategy behind both. The first goal is to make our own teams faster and better by turning AI projects into everyday ways of working. The second is to take what works and turn it into AI services and consulting packages that clients buy.

You'll spot where the market has gaps and build the bridge from those gaps to the technology we use to deliver service. You'll also be the person everyone at OuterBox goes to on AI.

You'll lead the AI engineering team, report to the EVP of Innovation, and work closely with Technology, who owns infrastructure and DevOps.

Job Responsibilities:

Reasonable accommodations may be made to enable individuals with disabilities to perform these essential functions

• Shape the AI vision and strategy with the EVP of Innovation. Decide where OuterBox is going with AI, inside the company and in the market, and what we build, buy, or skip. Models change fast, and a service built around today's gap can be dead in months.
• Find the gaps in the market and build the bridge to delivery. Turn them into services our delivery teams can run, and write the requirements the engineering team builds against.
• Run the internal AI projects that change how our teams work, from intake and build through pilot, rollout, and adoption. Make sure what ships gets used.
• Package what works into client services and consulting offers, including AI Development Services and GEO and LLM Optimization. Set scope, pricing, delivery owners, and the sales pitch. Focus on mid-market clients, where we already have relationships.
• Move AI services toward outcome and unit pricing as the cost per task keeps falling. Own the production deployments that keep client accounts and count toward our partner standing.
• Run our Anthropic program: certified practitioners, production deployments, public customer stories, and the quarterly scorecard. The EVP of Innovation owns the executive relationship and partnership strategy. Support the EVP on the AI side of our Google and Microsoft programs.
• Turn how our best people work into reusable agent skills and workflows.
• Present to group directors and clients, and to the leadership team and board alongside or on behalf of the EVP. Explain trade-offs in plain language. Run AI adoption through the AI liaisons, training, and certification paths, and join sales calls where AI is the pitch.
• Lead, coach, and develop the technical team. Run 1:1s and annual reviews, set priorities, and keep the team on AI services and adoption. Work with Technology on security, cloud governance, and reliability.
• Set KPIs for each initiative and report cost, adoption, delivery improvement, and AI services revenue in business terms.
• Test new models and tools. Recommend adopting or dropping each one, and say why.
• Additional duties, as assigned.

• 5+ years in AI, machine learning, or applied AI and automation, and 3+ years leading technical teams.
• A history of spotting gaps in the market and turning them into services, products, or platforms that customers paid for.
• Experience running internal AI projects and client-facing AI services or consulting, including taking an internal playbook and making it a sellable offer with scope, pricing, and delivery.
• Hands-on work with frontier AI models, including 1+ years with Anthropic Claude. You know agents, tool use and MCP, retrieval, prompt and context design, and evaluation.
• Working skill in Python or JavaScript/TypeScript and SQL. You can read code and review architecture with engineers and tell good work from fine.
• Experience with cloud platforms (Google Cloud preferred), Git, and CI/CD.
• Experience proposing AI initiatives and measuring results against cost, with ROI you can defend.
• Working knowledge of how digital marketing agencies deliver services, ideally paid media, SEO, and analytics.
• Comfort with outcome-based and unit pricing, and with moving a team away from hours-based work.
• A strong presenter who is at ease in front of executives, clients, and engineers.
• Experience building AI adoption, training, or certification programs. Partner program experience with Anthropic, Google, or Microsoft is a plus.
• Bachelor's degree in Computer Science, Data Science, Artificial Intelligence, or a related field. Equivalent work experience may be considered in lieu of a formal degree.