Senior Strategist

CourtAvenue • Chicago, IL

2d • $95,000 - $110,000

About The Position

CourtAvenue is a company of industry experts accelerating digital transformation for the world’s most ambitious companies. At CourtAvenue, you will be a part of a culture powered by entrepreneurs, technologists, data scientists and the habitually restless dedicated and energized to design products and services that transform businesses while optimizing them for growth. You will have the opportunity to learn and grow within a culture that values innovation while focusing on redesigning the experience between consumer and service (or product) by leveraging a fluid, seamless, and thoroughly transparent engagement.

A Senior Strategist at CourtAvenue helps set the course for the work. They lead strategic deliverables end-to-end — from research and synthesis through final presentation — and are increasingly trusted to own pieces of client accounts with oversight from department leadership. They’re often among the strongest voices in the room on a deliverable, bringing a clear point of view, sharp recommendations and the storytelling instinct to move clients forward. They’re entering the phase of their career where they’re building a reputation — internal teams know they can come to them for a strong recommendation, and clients begin to recognize them as a trusted strategic partner.

This role is grounded in commerce. The Senior Strategist will bring deep omnichannel shopper marketing experience to a portfolio of CourtAvenue clients — understanding how shoppers move across retail, digital and physical touchpoints, and translating that understanding into strategies that drive measurable commercial outcomes. They are fluent in the shopper journey, know how to brief and partner with retail media and creative teams, and can build the connective tissue between brand strategy and the moment of purchase.

Each of our strategists have their hands on keyboards. The Senior Strategist will research, structure and present full PPT deliverables, and use AI fluently as part of their craft — to synthesize inputs faster, pressure-test thinking, generate sharper ideas and elevate the quality and pace of every deliverable. A deep understanding of the digital landscape — latest trends, technologies and the implications for our clients — is required.

Requirements

• Bachelor’s degree in business, marketing, or related field required
• 5+ years of experience in digital strategy at an agency or consultancy
• Demonstrated omnichannel shopper marketing experience — fluency in the shopper journey across retail, digital and physical touchpoints, and a track record of strategies tied to commercial outcomes
• Proven experience developing and presenting full PPT deliverables — each of our strategists is hands on keyboard
• Strong use of AI in day-to-day strategy work — to synthesize deliverables, pressure-test thinking and generate ideas — with a clear point of view on how these tools elevate the craft
• Exceptional communication and presentation skills, both verbal and within written deliverables (PPT)
• Samples of previous deliverables that demonstrate your ability to lead strategic work and share strong recommendations rooted in customer needs and brand ecosystems
• Strong analytical and research skills, with experience using data and research tools and techniques
• Ability to partner closely with adjacent CA teams, including UX, data, creative and media
• Ability to be a self-starter and show proactivity when non-billable, sharing POV on value-add work you could bring to the agency during periods of softness

Responsibilities

• Lead strategic deliverables for key client accounts — stepping in with strong recommendations on how the work should come to life and owning the direction from kickoff through final presentation
• Serve as a day-to-day strategic partner for clients and internal teams, with internal teams knowing they can come to you for a strong POV, a clear approach or a high quality deliverable
• Bring omnichannel shopper marketing expertise to client work — connecting brand strategy to the shopper journey across retail, digital and physical touchpoints to drive measurable commercial outcomes
• Build and present full PPT deliverables end-to-end, leading with a clear point of view and sharp recommendations while remaining open to collaboration
• Use AI fluently and intentionally to synthesize research, generate ideas and accelerate the quality of deliverables — setting the pace for how the team works with these tools
• Conduct competitive, customer, industry and category analysis to set the context and current state for new client engagements
• Conduct and synthesize user research to support strategy, UX and creative deliverables
• Partner closely with adjacent CourtAvenue teams — UX, data, creative, media — often leading final deck creation on cross-department deliverables
• Provide guidance and day-to-day feedback to junior strategists on deliverables that need additional support, with the opportunity to formally manage a junior team member as the strategy team grows
• Write thought leadership on commerce, innovation, industry trends and future predictions — helping build the CourtAvenue strategy team brand externally
• Show proactivity during non-billable periods, sharing POV on value-add work you could bring to the agency or the team

What This Job Offers

• Job Type: Full-time
• Career Level: Senior