Creative Director

About Chubbies \& Cheekies

Chubbies is the outfitter of Fridays at five—a men’s lifestyle and apparel brand built for guys who work hard, have fun, and believe life is better when you don’t take yourself too seriously.

We make clothes with personality. From our signature shorts and swimwear to shirts, polos, outerwear, and everything in between, Chubbies brings more fun, color, confidence, and comfort to the way guys dress.

Cheekies is our women’s swim brand, with its own voice, audience, and opportunities for growth. Together, the two brands create opportunities to reach new customers, tell connected stories, and bring people together.

We’re looking for a Creative Director to lead creative across both brands—shaping how they look, sound, and show up through compelling storytelling, distinctive design, and content that makes people feel something.

The Opportunity

Reporting to the VP of Marketing, the Creative Director will lead creative strategy, concept development, art direction, copy, design, photography, and video for Chubbies and Cheekies.

You’ll work closely with the VP of Marketing to translate brand strategy into a clear creative vision that builds awareness, strengthens brand affinity, and supports business goals. Your scope will span brand campaigns, product storytelling, organic social, paid media, ecommerce, email and SMS, retail, wholesale, partnerships, and live experiences.

You’ll partner with the Director of Marketing to bring top-of-funnel marketing pillars to life through content, creators, collaborations, events, and cultural moments. You’ll also identify meaningful creative integration points between Chubbies and Cheekies—developing shared stories and experiences that strengthen both brands while preserving their distinct identities.

You’ll directly manage the Art Director and freelance copywriter, providing the direction, feedback, and leadership needed to deliver strong visual and written work. You’ll also guide external creative and production partners as projects require.

This is a hands-on leadership role. You should be equally comfortable developing a campaign concept, directing a shoot, shaping a headline, and reviewing a social edit. All responsibilities below span both brands.

What You’ll Own

Creative Vision \& Brand Identity

• Partner with the VP of Marketing to translate each brand’s positioning and strategy into a distinct creative direction.
• Define and evolve the visual identity, voice, and storytelling approach for Chubbies and Cheekies.
• Establish creative standards across design, copy, photography, video, and brand experiences.
• Build consistency across customer touchpoints while adapting creative to each channel and audience.
• Identify where shared creative can strengthen both brands and where each needs its own expression.

Campaign Concepts \& Storytelling

• Lead concept development for seasonal campaigns, product stories, brand initiatives, and collaborations.
• Turn audience insights, product benefits, and business priorities into compelling creative ideas.
• Develop campaign narratives that connect hero content with supporting channel executions.
• Direct the Art Director and freelance copywriter in translating concepts into cohesive visual and written work.
• Present concepts with a clear rationale and guide their development through feedback and production.
• Balance humor, personality, and cultural relevance with clear product communication.

Art Direction, Photography \& Video

• Lead art direction across campaign, lifestyle, studio, and ecommerce content.
• Guide casting, styling, locations, sets, composition, lighting, and overall visual treatment.
• Partner with production to define the approach, talent, resources, and deliverables needed for each shoot.
• Direct photographers, filmmakers, stylists, and other creative partners.
• Oversee editing, retouching, color, sound, and final creative quality.
• Ensure imagery represents products accurately while bringing each brand’s personality to life.

Copy \& Brand Voice

• Define and maintain a distinct voice for each brand across campaigns and customer touchpoints.
• Manage and brief the freelance copywriter on campaign narratives, headlines, product storytelling, and channel messaging.
• Review and refine copy for clarity, personality, consistency, and effectiveness.
• Ensure visual concepts and messaging work together to communicate a cohesive idea.
• Guide how each brand’s voice adapts across social, ecommerce, paid media, email, retail, and brand experiences.

Social \& Creator Content

• Partner with the Director of Marketing to develop creative that supports audience growth and cultural relevance across TikTok and other priority social channels.
• Develop recurring formats, original series, and content concepts suited to how people engage on each platform.
• Guide social storytelling, hooks, pacing, humor, and visual execution.
• Create briefs and creative frameworks that give creators room to bring their own perspective while staying connected to the brand.
• Use audience response and content performance to evolve ideas and improve execution.

Channel Creative \& Product Communication

• Lead creative across ecommerce, email, SMS, paid media, retail, and wholesale.
• Ensure product stories clearly communicate benefits, fit, features, and reasons to buy.
• Translate campaign concepts into channel executions with appropriate messaging, formats, and calls to action.
• Partner with Ecommerce, Retention, and Performance Marketing to understand channel needs and improve creative effectiveness.
• Guide testing of concepts, messaging, and formats while maintaining each brand’s identity.

Partnerships \& Brand Experiences

• Partner with the Director of Marketing to develop creative for collaborations, PR moments, grassroots programs, events, and community initiatives.
• Shape how each brand appears alongside partners through storytelling, content, design, and experiences.
• Extend creative ideas into physical environments, including activations, signage, displays, and event materials.
• Develop shared creative experiences that introduce audiences to both Chubbies and Cheekies.

Team Leadership \& Creative Execution

• Directly manage the Art Director and freelance copywriter, setting clear priorities, expectations, and creative direction.
• Mentor and develop the Art Director across concept development, visual storytelling, and execution.
• Provide specific, constructive feedback that strengthens both design and copy.
• Build a collaborative working relationship between art direction and copy so ideas develop together.
• Select, brief, and lead external creative partners as projects require.
• Partner with GTM Operations and production teams on briefs, priorities, timelines, and handoffs.
• Establish clear creative reviews and approvals to maintain quality and support timely delivery.
• Manage creative and production budgets within your scope.

What You Bring

• 8\+ Years of Experience leading creative for consumer, lifestyle, fashion, or apparel brands.
• A strong portfolio demonstrating original concepts, distinctive storytelling, and effective execution across channels.
• 8\+ Years of Experience developing creative for distinct brands or audiences while maintaining a clear identity for each.
• Strong art direction skills across photography, video, design, and physical brand experiences.
• Strong copy judgment, including the ability to guide brand voice, humor, headlines, and product storytelling.
• Experience managing art directors and freelance copywriters, with the ability to provide clear direction, develop talent, and hold partners accountable for quality.
• Experience directing shoots and working with photographers, filmmakers, stylists, talent, and production partners.
• Fluency in TikTok and other social platforms, with an understanding of what makes content engaging and shareable.
• Experience developing creative for ecommerce, paid media, email, retail, and wholesale.
• Ability to connect brand-building ideas with product communication and commercial goals.
• Ability to present ideas clearly, explain creative decisions, and incorporate feedback thoughtfully.
• Comfort using audience insights and performance results to improve creative.
• Sound judgment when balancing creative ambition, budgets, resources, and timing.
• A hands-on approach and willingness to contribute directly to the work.
• A sense of humor and appreciation for the personality, fun, and confidence that define Chubbies and Cheekies.

What Success Looks Like

• Distinct, recognizable creative identities for Chubbies and Cheekies.
• Campaigns and content that build awareness, affinity, and cultural relevance.
• Strong product storytelling that supports discovery and purchase.
• Social creative that gives audiences a reason to follow, engage, and share.
• Consistent, high-quality design and copy across digital channels and physical experiences.
• Meaningful creative integration between the brands that strengthens both.
• An Art Director and freelance copywriter who work with clear direction, productive collaboration, and high creative standards.