Job Description

Now Hiring: Associate Creative Director

Boston-Based | Hybrid Role  

There is a certain vibe in Boston that starts with its' people.

It's their sarcasm, their underlying rugged persona…and the one-of-a-kind culture they all embrace.

Knowing that there is no better way to share this with others than in the form of Boston's most culture-defining piece of headwear—the 'scally' cap—Boston Scally Company was soon established.

We aim to give those, not only from Boston, the opportunity to own a quality cap or shirt that represents our blue-collar mentality and the culture behind it. If you understand the tough, humble and loveable nature of Bostonians then you will understand Boston Scally Company.

The Role: Associate Creative Director

We're looking for a sharp, strategic, and style-savvy Associate Creative Director to lead brand and product storytelling across every touchpoint from packaging and campaigns to digital and retail for one of TDS's cornerstone brands.

This is a hands-on, hybrid creative leadership role that blends strong art direction with elevated design sensibility. You'll be critical in bringing the brand's personality to life and ensuring cohesive, compelling visual storytelling across channels. You'll thrive in a fast-paced, highly collaborative environment with a clear opportunity to make your creative mark.

What You'll Do

• Lead Brand Storytelling : Develop seasonal campaigns, art direction, and mood boards that reflect the brand's aesthetic and point of view.
• Drive Multi-Channel Creative : Design for packaging, paid ads, emails, site, social, and in-store—bringing consistency and commercial thinking to all outputs.
• Own the Creative Process : Lead projects from concept to final delivery, ensuring work is on-brand, on-brief, and on-time.
• Partner Cross-Functionally : Collaborate with product, marketing, ecommerce, and retail to create unified, effective creative.
• Produce Content That Performs : Direct photo and video shoots—including casting, styling, and on-set art direction—plus iterate creative based on performance metrics.

You Bring

• 3–5 years of experience in a creative or art direction role, ideally in men's fashion, accessories, or lifestyle brands.
• A strong portfolio showcasing campaign development, brand storytelling, and multi-platform creative execution.
• Hands-on experience directing content production, with a refined eye for styling, composition, and visual nuance.
• Proficiency with Adobe Creative Suite, Keynote, Figma, and other creative tools.
• Clear, confident communication skills and the ability to manage multiple work streams with efficiency and focus.
• A genuine interest in men's style, timeless design, and storytelling that moves people.

Additional Requirements

• Must be authorized to work in the U.S.
• Must be Boston-based or open to a hybrid work environment from our Boston office.
• A portfolio is required to be considered for this position.

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About The Digital Stronghold 

The Digital Stronghold (TDS) is a multi-brand e-commerce holding company aggregating digitally native companies in the men's interest space. It is currently composed of Taylor Stitch, The Tie Bar, Boston Scally, and Pedal Mafia. TDS exists to create an environment for men's interest brands to thrive together. 

At the heart of our belief is that when you have shared learnings, shared services, and shared centers of excellence, you can create something that propels both growth and profitability.

The Digital Stronghold is actively targeting additional brands for acquisition, allowing us to reach new customers through taste, style, and product assortment, driving both growth and market share. TDS is backed by Digital Fuel Capital, the leading private equity investor in the e-commerce space, providing both capital and in-house strategic and operational support to help brands scale successfully.

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