Creative Director

About Grayson Sky

Grayson Sky is a boutique creative marketing agency based in South Philadelphia. We specialize in developing innovative brand strategies, campaigns, and design systems that help our clients stand out and grow. Our close-knit team of passionate specialists is committed to making brands unforgettable and we hold our creative work to a high standard.

The Opportunity

We’re looking for a Creative Director to lead our design practice and serve as the creative backbone of the agency. This is a senior leadership role. You’ll set the creative vision across a portfolio of client accounts, mentor and manage a team of designers, and act as a strategic partner to both clients and agency leadership. You’ll own the quality, consistency, and evolution of creative output across every touchpoint.

Our clients span industries including finance, health and wellness, B2B SaaS, media, and professional services. You’ll work across brand identity, digital design, social, email, podcast and video content, print, and web UI, often all at once.

What You’ll Do

• Lead Creative Vision: Set and uphold the creative standard across all client accounts. Ensure every deliverable reflects strategic intent, brand integrity, and design excellence - from brand identity systems and campaign concepting to social content, digital ads, email, web UI, and print.
• Manage & Mentor Designers: Directly manage a team of graphic designers and serve as their primary creative resource. Provide clear direction, meaningful feedback, and ongoing development to build a strong, collaborative creative culture.
• Own Client Relationships: Lead client-facing creative conversations as the senior creative voice in the room. Facilitate intake, present creative, incorporate feedback, and proactively communicate project status. Build trust with clients by connecting design decisions to business outcomes.
• Drive Brand Systems: Develop and govern brand systems for clients across every touchpoint. Champion living brand documentation that scales - style guides, component libraries, asset templates - and ensure consistency is maintained as brands grow.
• Oversee Production Workflow: Maintain a clear view of all active projects, timelines, and capacity. Help prioritize work across the team, problem-solve when scope evolves, and ensure high-volume accounts (weekly podcast deliverables, recurring social, email campaigns) are executed on time without sacrificing quality.
• Collaborate on Strategy: Partner with agency leadership and account leads to shape creative strategy from the earliest stages of a project. Translate briefs into compelling creative directions and push concepts beyond the expected.
• Evolve the Agency’s Creative Voice: Bring fresh perspective to how Grayson Sky presents its own brand. Contribute to pitches, proposals, and agency marketing with the same rigor applied to client work.
• Stay Sharp: Monitor design, branding, and digital trends. Identify opportunities to integrate new tools, including AI-powered design tools, to improve efficiency and elevate output.

What You Bring

• 7+ years of professional design experience, with at least 2–3 years in a creative leadership or senior art direction role - agency experience strongly preferred.
• A portfolio that demonstrates range: brand identity, digital and social design, UI, print, and campaign work. Bonus points for complex, multi-touchpoint brand systems.
• Expert-level proficiency in Figma and Adobe Creative Suite (Photoshop, Illustrator, InDesign). Mailchimp, HubSpot or email platform experience is a plus.
• Proficient experience using AI tools like ChatGPT, Claude, Nano Banana, etc. for image generation, concepting, copy creation, outlining and more. 
• Strong design fundamentals and an eye for typographic craft, layout, and visual hierarchy.
• Proven ability to manage and develop designers with clarity not ego.
• Excellent communication skills: you can present creative work persuasively, write a clean client email, and run a productive meeting.
• Comfort with high-volume, deadline-driven environments. This agency moves fast across multiple client accounts simultaneously.
• A strategic mindset — you think about why design decisions are made, not just how they look.
• A degree in Graphic Design, Advertising Art Direction, or a related field is preferred but not required. What matters is the work.

Why Grayson Sky

Creative ownership: You’ll have real influence over the direction of creative work — both for clients and the agency itself.

Variety and depth: Our client roster spans industries, formats, and scales. No two weeks look the same.

A team that cares: We’re a small, collaborative group that takes the work seriously and treats each other well.

Growth: We support continued learning through industry events, courses, and exposure to new disciplines.

Flexibility: Hybrid work model based out of our South Philadelphia studio. We value presence and trust your judgment.

If you’re a senior creative leader ready to shape the direction of a growing boutique agency and do it alongside a team that genuinely loves what they do we’d love to hear from you.

Grayson Sky is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.