Digital Retail/Senior Retail Media Manager

Skai•Chicago, IL

14h•$100,000 - $120,000•Hybrid

About The Position

Skai is seeking a senior practitioner and strategic advisor for enterprise retail media clients. The role owns the strategy, performance, and outcomes of an assigned book of accounts, from planning through hands-on campaign execution. It combines deep channel expertise with strategic consulting, helping clients understand business results, diagnose performance, and develop actionable plans and narratives. Working with the Retail Media Expert Services Director, the position serves external clients and acts as a regional retail media expert for internal stakeholders, while contributing to the evolution of Skai’s platform. The role is US-based, hybrid, and may require travel of up to 10–15%.

Requirements

Demonstrated enterprise retail media ownership, accountable for strategy through execution rather than executing someone else’s plan.
Hands-on full-stack experience with Amazon and Walmart search and DSP, including Sponsored Products, Sponsored Brands, Sponsored Display, Amazon DSP, Walmart Connect sponsored search, Walmart DSP, Vendor Central, Seller Central, and the distinction between 1P and 3P.
Experience using Amazon Marketing Cloud (AMC) beyond out-of-the-box templates to answer questions that standard reporting cannot, build custom audiences and analyses (such as incrementality or multi-touch attribution), and inform client actions.
Strong analytical depth, including root-cause analysis and the ability to connect metrics to client business objectives rather than optimize solely to dashboard metrics.
Fluency in the retail media ecosystem, including retailer economics, onsite and offsite media, DSP, 1P and 3P, and shopper marketing, and understanding why tactics may perform differently across networks.
Advanced use of generative AI tools such as Claude to produce technical outputs, including reshaping data, reports, automations, and custom agents; a software engineering background is not required.
Ability to translate ambiguous client goals into strategies, plans, and narratives clients can present to their leadership, using Skai’s technology and appropriate partners.
Ability to work credibly with stakeholders ranging from analysts managing day-to-day work to executives who own budgets.
Experience operating cross-functionally in fast-paced, matrixed environments where delivery depends on teams outside the role’s reporting line.
Strong ownership and follow-through, including taking problems to resolution and addressing unowned work.
US-based.
Ability to travel up to 10–15%.

Nice To Haves

Breadth across other 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 more important than depth in one.
Agency-side background; candidates from brand, retailer, and platform backgrounds are also welcome.
Coaching or informal leadership experience, such as mentoring or training colleagues or building lasting playbooks and documentation; interest in growing into people management.
Commercial exposure to retention and growth of a book of business, QBRs with economic buyers, or scoping new work.
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

Own the strategy, performance, and outcomes of an assigned book of enterprise retail media accounts.
Plan, build, and optimize campaigns hands-on across Amazon, Walmart, Instacart, Target, and other retail media networks, including day-to-day account management as needed.
Investigate performance issues and opportunities and make actionable recommendations to clients.
Advise senior client stakeholders on media planning, budget allocation across networks, and retail media best practices.
Lead QBRs and strategic reviews, and support the client services team with renewals, growth conversations, and escalations.
Build custom analyses, reports, and automations when standard tools and templates are insufficient.
Serve as the regional retail media subject matter expert and support internal stakeholders across the business.
Mentor less experienced colleagues and contribute to team playbooks and processes.
Partner with product development, sales, technical account management, and sales engineers to drive platform innovation and capture market opportunity.