Director Retail Media

Skai•Chicago, IL

7d•$120,000 - $140,000•Hybrid

About The Position

Skai is seeking a Director of Expert Services, Retail Media, a key leadership role on the Expert Services team. This position is responsible for upholding the quality of work, clarity of communication, and building confidence with enterprise clients and Skai leadership. The role requires a blend of strategy, commercial judgment, and executive influence to navigate the retail media landscape and translate it into actionable direction. The Director will extend the function's reach into new business and thought leadership, reporting directly to the Expert Services Global Lead and operating with a high degree of independence and trust. This role will support internal stakeholders and contribute to the future development of Skai's platform.

Requirements

Leadership and business acumen.
Senior retail media leadership: Led teams of practitioners and been accountable for a portfolio of enterprise retail media clients, from strategy through execution, ideally with mid-senior staff and up reporting to you.
Commercial acumen: Connect media decisions to client unit economics and business outcomes, and have helped retain, grow or scope a book of business.
Executive presence and influence: Persuade senior stakeholders, internal and external, without relying on authority, and comfortably challenge a client executive or colleague when the evidence calls for it.
Independent judgement: Operate with minimal direction, comfortable with ambiguity, and own decisions and outcomes.
Standard-setting and communication craft: Raised the quality bar of a team, given direct feedback, and turned complex analysis into a clear narrative and a strong deck.
Retail media depth: Amazon and Walmart full stack (search and DSP), credible enough to challenge a plan at the level of detail and not only the headline.
AMC and measurement: Understand how AMC and other approaches answer what standard reporting cannot for different client types (CPG, consumer electronics, home & garden…), and when a metric is misleading the client.
Retail media ecosystem fluency: Understand how retailer economics, onsite, offsite and DSP, 1P and 3P, and shopper marketing fit together, and why a tactic that works on one network fails on another.
Advanced use of generative AI tools such as Claude to raise your own output and your team's, from analysis to automations and custom agents.
New business and thought leadership: Helped win work through pitches, audits or scoping, and have a point of view shared through speaking, writing or frameworks.

Nice To Haves

Agency-side background.
Breadth across other retail media networks: Instacart, Target and Roundel Media Studio, Criteo, CitrusAd, Epsilon, Kroger Precision Marketing, Amazon Retail Ad Service. Breadth across several matters more than depth in any single one.
Total commerce context: Familiarity with how retail media sits alongside shopper marketing, trade budgets and joint business planning with retailers.
Skai, or a comparable retail media or search management platform.
Collaborating with a global team, both locally and virtually.

Responsibilities

Act as the leader's trusted deputy, representing the function and its priorities in every room.
Help define and uphold the standard for the quality of our work, from account plans and methodology to analyses, QBRs, decks and client communications.
Shape the strategy of Expert Services with the leader, including the service model, coverage and capacity, how our offering is packaged, and how the team uses AI to raise quality and capacity.
Support strategic accounts as an executive voice, leading escalations, performance resets, renewals, growth conversations and executive business reviews.
Lead or co-lead pitches, audits and scoping with Sales, and develop thought leadership (points of view, frameworks, talks and articles) as an external voice of Skai Expert Services.
Hire and coach Directors, Managers and Specialists, hold them accountable to their commitments, and build the playbooks and succession that sustain the team.
Influence senior stakeholders inside and outside Skai, and partner with product, sales, client services, technical account management and sales engineers to bring client and market evidence into the roadmap.