Director, Data Strategy and AI

STRATEGY / Lead cross-functional data and AI initiatives that strengthen Octagon’s client analytics programs and accelerate internal adoption of practical AI-enabled workflows — partnering closely with technical specialists and business stakeholders to deliver measurable outcomes.

Our headquarters are in Stamford, CT, but the location of this position can be flexible with priority given to candidates open to hybrid work (3 days week in office) in one of our office locations - - Stamford, CT, New York, NY, Charlotte, NC, Atlanta, GA, Chicago, IL, Los Angeles, CA, and Miami, FL. We will also consider a remote-based working arrangement for qualified candidates.

Octagon is on the hunt for a new Director, Data Strategy and AI. In this role, you’ll help the team pick the right problems to solve, keep the work moving, and make sure what we build actually gets used — whether that’s client-facing analytics or internal AI tools. You can talk shop with engineers and analysts, then turn around and explain the “so what” in plain English to account leads and clients. You’ll also keep leaders in the loop, flag risks early, and clear roadblocks, without needing to personally build every dashboard, pipeline, or model. You’re someone who enjoys working at the intersection of data, technology, and the day-to-day realities of a client service business. 

THE WORK YOU’LL DO

• Client Strategy and Sponsorship Analytics
  • Lead the data strategy for major brand partners including sponsorship measurement, investment analysis, and performance reporting across complex, multi-platform programs
  • Serve as the senior data point of contact in client-facing engagements — translating analytical findings into actionable sponsorship strategy for CMOs, brand strategists, and senior marketing stakeholders
  • Design and own the measurement infrastructure for each client program: data structures, KPI frameworks, reporting systems, and automation workflows tailored to each brand's existing ecosystem
  • Support new business development by architecting analytics packages, contributing to RFI and RFP responses, and demonstrating the agency's data capability to prospective clients
• AI Product Ownership and Internal Tooling
  • Own the roadmap and prioritization of Octagon’s internal AI-enabled tools — aligning stakeholders on the highest-value use cases and ensuring work moves from prototype to production with clear outcomes.
  • Partner closely with Solutions Engineering and Data Engineering to translate business problems into scoped requirements, clarify dependencies, and drive delivery from discovery through launch.
  • Establish a lightweight operating cadence (goals, milestones, success metrics) and ensure internal tools drive measurable efficiency and quality gains across account, strategy, partnerships, research, and new business teams.
  • Stay current on the AI landscape and speak credibly about prompt engineering, agent development, and evaluation at a strategic level — enabling sound build-vs-buy decisions and removing blockers to production-grade deployment.
• Infrastructure and Technical Leadership
  • Partner with engineering to shape the data and AI foundations that support client analytics and internal tools (e.g., pipelines, databases, search/retrieval layers, APIs), with a focus on scalability, reliability, and fit-for-purpose design.
  • Help coordinate and oversee key analytics environments (e.g., Posit Connect/Workbench or equivalent) and cloud resources in partnership with technical owners, ensuring reliability, security, and appropriate governance.
  • Ensure the team has the right approach to turning multi-source data (social, media, audience, contract, performance) into analysis-ready models — clarifying requirements, sequencing dependencies, and keeping delivery moving.
  • Guide data governance expectations (access controls, documentation, observability) in partnership with enterprise teams, balancing compliance requirements with the speed needed to deliver value.
• Team Development and Cross-Functional Leadership
  • Lead and develop a multidisciplinary team (currently a Senior Analyst, a Solutions Engineer, and a Data Engineer) — setting clear priorities, protecting focus time, and empowering high agency while balancing client delivery and internal product work.
  • Drive alignment across account, strategy, partnerships, research, and technical teams — translating needs and constraints, unblocking dependencies, and redirecting work when priorities or assumptions change.
  • Navigate holding-company and enterprise governance (procurement, security, technology standards) — coordinating transitions, clarifying timelines, and advocating for Octagon’s needs without slowing delivery.

THE TEAM YOU'LL JOIN

Recognized as one of the “Best Places to Work in Sports”, Octagon is the global sports, entertainment, and experiential marketing arm of the Omnicom Group.

We take pride in being Playmakers – finding insightful, bold ways to create play in our work, our lives, and in the world. We believe in the power of play to create big ideas and unlock potential for our clients and talent.

We can put ourselves in the shoes of fans because we ARE fans – of sports, entertainment, and culture at large. This expertise allows us to continually evolve the fan experience across sports and entertainment alongside some of the biggest brands and talent in the world.

The world needs play more than ever. Are you a Playmaker?

WHO WE'RE LOOKING FOR

• 6+ years in data analytics, data strategy, product operations, or a related function — with experience leading cross-functional work and delivering analytics or data products in a client- or stakeholder-facing environment
• Background in marketing/advertising agencies, sports and entertainment partnerships a major plus
• Strong analytical fluency (e.g., SQL and/or R/Python) with the ability to work effectively with engineers and analysts; you don’t need to be the primary builder of pipelines, but you should be able to ask great questions and evaluate tradeoffs
• Demonstrated ability to set priorities, manage dependencies, and drive execution across multiple teams; prior people management is a plus but not required
• Understanding of the AI product lifecycle (prototype to production) and what production-grade deployment involves, with the ability to speak credibly about prompt engineering, agent development, and evaluation frameworks at a strategic level (hands-on experience is a plus)
• Comfort working in a modern data/AI stack (cloud, APIs, basic security concepts) and partnering with technical owners on decisions; familiarity with AWS/Linux/Posit (or equivalents) is helpful but not required
• Excellent communication and stakeholder management skills — able to represent technical work clearly and credibly, build trust across functions, and create space for specialists to own their domains
• Ability to navigate governance and compliance constraints in a complex organization (data access, privacy, vendor/tool approvals) and keep work moving by proactively removing blockers
• Familiarity with modern AI/search concepts (embeddings, vector search, retrieval patterns) — enough to partner effectively with engineers and vendors
• Exposure to AI agent patterns and multi-step automation workflows (framework experience is a plus, not a requirement)
• Experience integrating tools into enterprise productivity ecosystems (e.g., Microsoft 365/SharePoint/Teams, Power Platform, Google Workspace) is a plus
• Background in sponsorship, sports marketing, or media measurement — including familiarity with audience data, brand tracking, social listening, and campaign performance datasets
• Familiarity with how production data/AI systems are operated (monitoring, reliability, release processes) and how teams reduce risk while shipping quickly

The base range for this position is $110,000 – 130,000. Where an employee or prospective employee is paid within this range will depend on, among other factors, actual ranges for current/former employees in the subject position; market considerations; budgetary considerations; tenure and standing with the company (applicable to current employees); as well as the employee’s/applicant’s background, pertinent experience, and qualifications.

Octagon is proud to be an Equal Opportunity/Affirmative Action employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, citizenship, disability, protected veteran status, or any other basis prohibited by law.