Director Retail Media

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

Benefits offered by this job

Hybrid work model

Global team culture

Job summary

Skai seeks a Director of Expert Services to lead a high-impact team delivering top-tier retail media consulting for enterprise clients. You will shape service strategy, drive executive-level communications, and partner with product, sales and client services to align roadmap with market needs.

You will be instrumental in hiring, coaching, and building scalable playbooks, while leveraging AI tools to raise quality and capacity across engagements.

Qualifications

• Experience leading enterprise retail media teams and portfolios.
• Ability to translate analytics into executive-ready narratives.
• Proven track record in driving client growth and renewals.
• Strong stakeholder management and cross-functional collaboration.
• Comfort with ambiguity and independent decision-making.

Responsibilities

• Act as the leader's deputy, defining quality standards for work and client communications.
• Shape Expert Services strategy including the service model, coverage and capacity.
• Lead escalations, renewals, and executive business reviews for strategic accounts.
• Lead pitches, audits, and scoping with Sales; develop thought leadership.
• Hire and coach Directors and Managers, build playbooks and succession.
• Influence senior stakeholders and align roadmap with product and sales.

Skills

Retail media leadership

Commercial acumen

Executive presence

Independent judgement

Communication craft

Thought leadership

Tools

Claude AI

Job description

Ready to take your career to the next level?

Skai is looking for the best and the brightest to join our family. We're proud of our industry-leading digital marketing software but we're even prouder of the people behind it. That's where you come in!

The Director of Expert Services, Retail Media is a key leadership role on the Expert Services team and the right hand of the function's leader. You hold the standard for the quality of our work, the clarity of how we communicate it, and the confidence our enterprise clients and Skai leadership place in us.

The role sits where strategy, commercial judgement and executive influence meet. You walk into a room with a CMO, a retailer or our own leadership team and carry it, turning a fragmented and fast-moving retail media landscape into direction people act on, and you extend the reach of the function into new business and thought leadership.

Reporting directly to the Expert Services Global Lead, you will work with a high degree of independence and trust, supporting internal stakeholders and helping shape where Skai's platform goes next.

Duties and Responsibilities

• Act as the leader's trusted deputy, representing the function and its priorities in every room, and 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

DIRECTOR OF EXPERT SERVICES

Requirements:

Position Requirements

We care more about what you have done than how long you have been doing it, so the requirements below are written as evidence rather than years. Expect to speak to them concretely.

Leadership and business acumen, required

• Senior retail media leadership. You have 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. You 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. You persuade senior stakeholders, internal and external, without relying on authority, and you are comfortable respectfully challenging a client executive or colleague when the evidence calls for it.
• Independent judgement. You operate with minimal direction, are comfortable with ambiguity, and own your decisions and outcomes.
• Standard-setting and communication craft. You have raised the quality bar of a team, given direct feedback, and turned complex analysis into a clear narrative and a strong deck.

Technical and growth skills, required

• 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. You know how AMC and other approaches answer what standard reporting cannot for the different types of clients (CPG, consumer electronics, home & garden...), and when a metric is misleading the client.
• Retail media ecosystem fluency. 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. A software engineering background is not required.
• New business and thought leadership. You have helped win work through pitches, audits or scoping, and have a point of view you have shared through speaking, writing or frameworks.

Strongly preferred

• Agency-side background. This is the most directly relevant experience for the role, though we welcome strong candidates from the brand, retailer and platform sides.
• 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 to us 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.

Location and travel

• US-based
• Ability to travel as needed for clients, pitches and industry events

We are hybrid for the long term - with a great home/ office work mix, passionate and diverse team members, and a vibrant company culture.

The salary range for this position is $120,000-140,000. The actual salary amount will vary depending on the applicants experience, skills and abilities as well as internal equity and market data. This position is eligible for additional bonus compensation, full details will be provided during the recruitment process.

Equal Opportunity Employer

Skai, Inc. is an Equal Opportunity Employer. At Skai, we believe ensuring a diverse, equitable, and inclusive workplace is not just an ideal to strive for; it is right, necessary, and our responsibility as humans. Our full DE&I commitment and global framework can be viewed on our company website and are aligned to our core values. We strongly encourage and seek applications from women, people of color, and bilingual and bicultural individuals, as well as members of the lesbian, gay, bisexual, and transgender communities. Applicants shall not be discriminated against because of race, religion, sex, national origin, ethnicity, age, disability, political affiliation, sexual orientation, gender identity, color, marital status, medical condition including acquired immune deficiency syndrome (AIDS) and AIDS-related conditions, or any other protected status. Also pursuant to the San Francisco Fair Chance Ordinance, we encourage and will consider for employment qualified applicants with arrest and conviction records.

Applicants with Disabilities

Reasonable accommodation will be made so that qualified disabled applicants may participate in the application process. Please advise in writing of special needs at the time of application.

Skai is an E-Verify employer