Director Retail Media

Skai•Chicago, IL

10d•$120,000 - $140,000•Hybrid

About The Position

The Director of Expert Services, Retail Media is a senior leadership role and trusted deputy to the function’s leader. The position sets standards for the quality of the team’s work and its communications, and builds confidence with enterprise clients and Skai leadership. It combines strategy, commercial judgment, executive influence, new-business support, and thought leadership. Reporting directly to the Expert Services Global Lead, the Director works independently to support internal stakeholders and help shape Skai’s platform roadmap. The role helps define the Expert Services strategy, service model, coverage and capacity, packaging, and use of AI. It also provides executive support to strategic accounts, leads or co-leads pitches and audits, develops external thought leadership, and hires and coaches team members. The position is US-based and requires travel as needed for clients, pitches, and industry events. Skai describes its long-term working arrangement as hybrid, with a mix of home and office work. The salary range is $120,000–$140,000, with eligibility for additional bonus compensation; actual salary depends on experience, skills, abilities, internal equity, and market data.

Requirements

Senior retail media leadership experience, including leading practitioner teams and being accountable for a portfolio of enterprise retail media clients from strategy through execution; experience managing mid-senior staff and above is preferred within this requirement.
Commercial acumen connecting media decisions to client unit economics and business outcomes, with experience helping retain, grow, or scope a book of business.
Ability to persuade senior internal and external stakeholders without relying on authority, and to respectfully challenge executives or colleagues when evidence supports it.
Ability to work independently with minimal direction, navigate ambiguity, and own decisions and outcomes.
Experience raising a team’s quality bar, giving direct feedback, and turning complex analysis into clear narratives and strong presentations.
Deep retail media expertise across Amazon and Walmart full stack, including search and DSP, with the ability to challenge plans in detail.
Knowledge of AMC and other measurement approaches, including how they address questions beyond standard reporting for different client types and how to identify misleading metrics.
Fluency in the retail media ecosystem, including retailer economics, onsite and offsite media, DSP, first- and third-party data, and shopper marketing, and understanding of differences between networks.
Advanced use of generative AI tools such as Claude to improve personal and team output through analysis, automation, and custom agents; software engineering experience is not required.
Experience helping win work through pitches, audits, or scoping, and a point of view shared through speaking, writing, or frameworks.
US-based.
Ability to travel as needed for clients, pitches, and industry events.

Nice To Haves

Agency-side background; strong candidates from brand, retailer, and platform sides are also welcome.
Breadth across retail media networks such as Instacart, Target and Roundel Media Studio, Criteo, CitrusAd, Epsilon, Kroger Precision Marketing, and Amazon Retail Ad Service; breadth across several networks is valued over depth in one.
Familiarity with total commerce, including how retail media relates to shopper marketing, trade budgets, and joint business planning with retailers.
Experience with Skai or a comparable retail media or search management platform.
Experience collaborating with a global team, both locally and virtually.

Responsibilities

Represent the Expert Services function and its priorities as the leader’s trusted deputy.
Define and uphold standards for account plans, methodologies, analyses, QBRs, presentations, and client communications.
Shape the Expert Services strategy, including its service model, coverage and capacity, offering packages, and use of AI.
Serve as an executive voice for strategic accounts, leading escalations, performance resets, renewals, growth conversations, and executive business reviews.
Lead or co-lead pitches, audits, and scoping with Sales.
Develop thought leadership, including 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 for commitments, and develop playbooks and succession plans.
Influence senior stakeholders inside and outside Skai.
Partner with product, sales, client services, technical account management, and sales engineers to bring client and market evidence into the product roadmap.