Director of Retail Media Strategy & Expert Services

Qumra Capital; Chicago (IL); Hybrid; USD 120,000 - 140,000; Full time

Job summary

Skai is seeking a Director of Expert Services, Retail Media in Chicago to lead a high-impact team and serve as the executive voice for retail media strategy and delivery.

The role sits at the intersection of strategy, commercial judgment and leadership influence, shaping offerings and using AI to enhance quality and capacity. You will collaborate with product, sales and client services to drive growth and client outcomes.

Qualifications

• Senior retail media leadership with responsibility for enterprise client portfolios.
• Commercial acumen linking media decisions to client unit economics.
• Executive presence influencing senior stakeholders inside/outside the company.
• Independent judgement with minimal direction and clear ownership.
• Ability to raise the quality bar and communicate complex analyses clearly.

Responsibilities

• Act as deputy to the function leader, upholding work quality and client communications.
• Shape Expert Services strategy, service model, coverage and capacity.
• Lead escalations, renewals, growth conversations and executive reviews.
• Lead or co-lead pitches, audits and scoping with Sales and develop external thought leadership.
• Hire, coach and build playbooks for Directors and Managers; drive succession.
• Influence product, sales and technical teams with market evidence for the roadmap.

Skills

Senior leadership

Commercial acumen

Executive presence

Independent judgement

Communication craft

Retail media depth

AMC and measurement

Ecosystem fluency

Generative AI expertise

New business & thought leadership

Tools

Claude AI tools

Job description

Skai is seeking a Director of Expert Services, Retail Media in Chicago to lead a high-impact team and serve as the executive voice for retail media strategy and delivery.

The role sits at the intersection of strategy, commercial judgment and leadership influence, shaping offerings and using AI to enhance quality and capacity. You will collaborate with product, sales and client services to drive growth and client outcomes.