Director Strategy Jobs in Chicago, IL (NOW HIRING)

DIRECTOR, STRATEGY (Part-time, hourly)

Role Summary

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

Directors shape the work by clarifying the problem, organizing inputs, developing strategic recommendations, and connecting thinking to creative and design outcomes including brand identity, messaging, campaigns, experiences, content, and other forms of activation.

This role is often the connective tissue between leadership, client teams, creative and engagement partners, and other collaborators. A strong Director moves fluidly between analysis and storytelling, detail and synthesis, confidence and curiosity and knows when to take the lead and when to ask for guidance.

ESSENTIAL DUTIES AND RESPONSIBILITIES

Bring clarity to complex client challenges

• Develop a strong understanding of the client's business, audience, category, culture, and competitive context.
• 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 work organized, focused, and moving.
• Anticipate risks, gaps, and open questions early and manage up when guidance, alignment, or a decision is needed.

Apply core strategy tools and methods

• Use foundational strategy tools including research inputs, stakeholder interviews, audits, workshops, and synthesis frameworks to 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 moves the work forward.

Shape clear, useful strategic work

• Turn complex inputs into concise, well-structured deliverables (briefs, narratives, and recommendations) that are easy to act on.
• Connect strategic thinking to creative and design outcomes, including brand identity, messaging, campaigns, experiences, and content.

Support the work, the relationship, and the Strategy practice

• Partner with Leadership, Engagement Leads, and cross-functional collaborators to keep work focused, well-organized, and on track against scope, timing, and quality expectations.
• Bring forward ideas, tools, examples, and points of view that strengthen 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 below are representative of the knowledge, skill, and/or ability required.

• Bachelor's degree or higher, with 6-10 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.
• Working command of foundational strategy tools and methods, including strategic frameworks, stakeholder interviews, workshop facilitation, qualitative and quantitative research, competitive and 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.
• Demonstrated ability to lead significant workstreams, collaborate across disciplines, and contribute to healthy engagement delivery.
• Willingness to manage up, ask for guidance when needed, and actively build strategic range and rigor over time.

WHAT SUCCESS LOOKS LIKE

A successful 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.
• Goes beyond the obvious answer (pressure-testing the thinking and building fluency across clients, categories, and methods).
• Simplifies a story so others can understand it and act on it.
• Manages up effectively and raises their hand when they need help, context, or direction.
• Understands that great strategy is not just insight, it is direction people can act on.