Independent Associate Jobs in Chicago, IL (NOW HIRING)

Open role in VSA Office locations, including New York, and Chicago; Hybrid work schedule 

Visa Sponsorship is not available for this position, now or in the future. Applicants must be legally authorized to work in the United States on a permanent basis without requiring employer sponsorship.

Role Summary

The Associate Director, Strategy is a senior strategy practitioner who helps turn complex client situations into clear, actionable direction. This role is expected to bring structure to ambiguous problems, build trust with clients and internal teams, and lead significant strategy workstreams with increasing independence.

Associate Directors help shape the work by clarifying the problem, organizing the inputs, developing strategic recommendations, and connecting the thinking to creative and design outcomes. That includes understanding how strategy informs brand identity, messaging, campaigns, experiences, content, and other forms of activation.

This role is often the connective tissue between senior strategy leadership, client teams, creative and engagement partners, and other collaborators. A strong Associate Director can move between analysis and storytelling, detail and synthesis, confidence and curiosity, while knowing when to take the lead and when to ask for guidance.

Essential Duties and Responsibilities (Other duties may be assigned)

Bring clarity to complex client challenges

• Develop a strong understanding of the client's business, audience, category, culture, and competitive context.
• Help translate research, data, stakeholder input, and team discussion into clear strategic implications, choices, and recommendations.

Lead strategy workstreams with increasing independence

• Own significant strategy workstreams or smaller engagements, keeping the work organized, focused, and moving.
• Anticipate risks, gaps, or open questions early, and manage up when guidance, alignment, or a decision is needed.

Apply core strategy tools and methods

• Use foundational strategy tools, research inputs, stakeholder interviews, audits, workshops, frameworks, and synthesis to help structure the work and develop stronger recommendations.
• Know when to apply a familiar method, when to adapt the approach, and when to seek guidance from senior strategy leadership.

Build client confidence

• Develop trusted working relationships with clients through preparation, responsiveness, judgment, and clear communication.
• Lead client conversations and presentations in a way that invites useful dialogue, manages expectations, and helps move the work forward.

Shape clear, useful strategic work

• Turn complex inputs into concise, well-structured deliverables, briefs, narratives, and recommendations.
• Connect strategic thinking to creative and design outcomes, including brand identity, messaging, campaigns, experiences, content, and other forms of activation.

Support the work, the relationship, and the Strategy practice

• Partner with Directors, Engagement Leads, and cross-functional partners to keep the work focused, well-organized, and moving against scope, timing, resources, and quality expectations.
• Bring forward ideas, tools, examples, and points of view that improve the work while continuing to build strategic range, rigor, and confidence over time.

Qualifications - To perform this job successfully, an individual must be able to perform each essential duty satisfactorily. The requirements listed below are representative of the knowledge, skill, and/or ability required. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.  

• A Bachelor's degree, or a more advanced degree, with 6-9 years of experience in brand strategy, marketing strategy, communications strategy, customer/audience strategy, consulting, research, or a related discipline.
• Experience developing insights, strategic recommendations, positioning, messaging, creative briefs, experience principles, or other client-ready strategy deliverables.
• A working command of foundational strategy tools and methods, including strategic frameworks, stakeholder interviews, workshop support, qualitative and quantitative research inputs, competitive/category analysis, audience insight development, and synthesis.
• Strong writing, presentation, facilitation, and communication skills.
• Comfort working across different clients, categories, assignment types, and levels of ambiguity.
• Ability to lead significant workstreams, collaborate across disciplines, and contribute to healthy engagement delivery.
• Ability to manage up, ask for guidance when needed, and continue building strategic range and rigor over time.

What success looks like:

A successful Associate Director, Strategy:

• Makes complex situations feel clearer and more manageable.
• Builds client trust through preparation, judgment, and presence.
• Takes ownership without over-isolating or over-controlling the work.
• Balances rigor with momentum.
• Shows curiosity and learning discipline by going beyond the obvious answer, pressure-testing the thinking, and continuing to build fluency across clients, categories, and strategic methods.
• Knows how to simplify a story so others can use it.
• Knows how to manage up and raise their hand when they need help, context, or direction.
• Understands that great strategy is not just insight; it is direction people can act on.

Total Perks Package

• The chance to be a part of a growing company and the next success story
• Amazing opportunities for career development
• Recognition programs
• Employee referral bonus
• Fun and collaborative work environment
• Casual dress code
• Insurance Coverage (medical, dental, vision, life, and disability)
• 401(k) retirement plan, with employer 4% match
• Work/life benefits, including mental health and wellbeing support
• Flexible Time Off Policy
• Paid holidays, including agency soft closing Christmas Eve-New Year's Day
• Paid leave options, including sick leave, medical leave for self and family, and parental leave