Lead Creative Strategist

an OuterBox company•Chicago, IL

2d•$85,000 - $100,000

About The Position

Lead Creative Strategists own the vision, quality, and execution of creative asset development across Accelerated Digital Media, an OuterBox company’s Paid Media channels, including Paid Search, Paid Social, and Programmatic. You will guide the creative team in producing high-performing assets, collaborate directly with clients, and establish the processes, standards, and cost frameworks that underpin our Creative Services offering. This role blends strategic thinking, hands-on creative leadership, data-informed decision-making, and operational rigor. You will work cross-functionally with client services, paid media strategists, and agency leadership to ensure our creative output not only looks exceptional—but directly drives measurable business outcomes.

Requirements

5+ years of experience preferred. Demonstration of exemplary performance may supersede the experience requirement.
Experience leading a team to meet goals and deliver successful outcomes. You are capable of guiding, coaching, and having constructive conversations.
Strong understanding of digital marketing channels and best practices.
Proficiency in creative tools such as Adobe Creative Suite, Canva, or similar.
Excellent storytelling, copywriting, and content creation skills.
Analytical mindset with the ability to interpret data and make data-driven decisions.
Strong project management skills and the ability to handle multiple projects simultaneously.
Exceptional communication and presentation skills.
Ability to work both independently and collaboratively in a fast-paced environment.
Experience with performance marketing and understanding of key metrics such as ROI, CPC, CPA, and conversion rates.
Familiarity with A/B testing and optimization techniques.
Experience working with creative AI tools
Strong problem solving & critical thinking skills. You can identify underlying issues, listen actively, and collaboratively develop solutions that are most helpful and appropriate, considering all angles of a challenge/problem and putting yourself in your teammate’s and client’s shoes.
We are unable to sponsor or take over sponsorship of an employment Visa at this time.

Responsibilities

Lead the development and execution of creative strategies for Paid Social (Meta, LinkedIn, TikTok, etc.), Paid Search, Google Ads, and Programmatic channels.
Oversee all creative asset production—including video, static, motion graphics, ad copy, and interactive formats—to meet performance and brand goals.
Act as the creative point of contact for clients, helping communicate vision, rationale, timelines, and results.
Manage the end-to-end creative workflow from brief → concept → production → delivery, ensuring work is on time, on brand, and aligned with platform best practices.
Partner closely with Paid Media teams to determine required creative asset mixes, testing cadences, and refresh cycles.
Ensure creative output ladders to audience insights, funnel stages, platform requirements, and client objectives.
Build and continuously refine OuterBox’s Creative Services processes across intake, scoping, revision cycles, QA, and delivery.
Develop standardized cost models, packages, and pricing guidance for creative production used across proposals, renewals, and cross-sells.
Create templates, briefs, SOPs, and resource libraries to improve efficiency, scalability, and cross-team consistency.
Lead client-facing creative discussions, from concept pitches to final asset reviews.
Translate client goals into clear creative direction and ensure alignment throughout the project lifecycle.
Support client services teams in communicating performance insights, strategic evolution, and creative recommendations.
Analyze creative performance data in partnership with Paid Media teams to determine what’s working, what’s not, and what to test next.
Use performance insights to evolve creative strategies, test roadmaps, and future asset direction.
Build and maintain internal creative resources, including design tools, AI creative software, templates, brand kits, and stock image/video libraries.
Champion the adoption of new technologies and creative approaches (AI, automation, advanced formats, new testing methodologies).
Help position OuterBox’s Creative Services as a competitive differentiator across pitches, marketing materials, and internal training.
Conduct regular 1:1 meetings and annual performance reviews with direct reports, providing constructive feedback and setting goals for continuous professional development and growth of team members.
Foster collaborative environment amongst team to promote integrated alignment and holistic strategies & communication for portfolio of accounts.
Empower team members to own results, communication and implementation for their specific channels as well as joint successes and opportunities across clients to promote teammate development.
Partner with all departments across OuterBox in alignment with company vision and goals. Every department contributes to creating opportunities for our clients, providing a great experience, and retaining our clients.
Continuously stay updated on the digital marketing industry & related industry verticals to grow your knowledge and build credibility with teammates and clients.
Participate in ongoing BSchool training to build credibility & business acumen with both teammates and clients, and share your insights.
Additional duties, as assigned.