Director Headwear Merchandising

L2 Brands•Baltimore, MD

12d

About The Position

L2 Brands is hiring a Director Headwear Merchandising to lead assortment strategy, seasonal direction, and go-to-market execution for the Legacy and Ouray headwear portfolios. The role serves as the commercial leader for headwear, ensuring products are developed, positioned, and launched to support growth, profitability, and long-term brand strength across multiple brands and sales channels. The Director defines and manages channel-specific assortments, sets seasonal merchandising direction, and partners with Product Development, Production, Planning, Creative Art, Marketing, Sales, and Training to bring products and selling stories to market. The role oversees product launches, samples and decoration direction, trade-show and brand-activation representation, photoshoot and content planning, and merchandising analytics. It also leads and develops the Headwear Merchandising team and supports the adoption of AI tools to improve planning, analysis, and workflow efficiency. This is a full-time, salaried position based in a professional office environment, with remote or hybrid work noted in the posting. Approximately 50% travel is expected for trade shows, customer meetings, brand activations, and team collaboration. The position reports to the Chief Experience Officer and offers the opportunity to influence the strategic direction of a growing multi-brand organization.

Requirements

Bachelor's degree in Merchandising, Business, Marketing, or a related field.
10+ years of merchandising, product management, or related leadership experience.
Extensive experience leading headwear merchandising strategies within lifestyle, apparel, or consumer goods brands.
Proven success leading assortment strategy, product launches, and category growth initiatives.
Strong commercial acumen and ability to balance customer needs, brand direction, and financial performance.
Experience partnering closely with Product Development, Creative Art, Marketing, Planning, and Sales teams.
Demonstrated success building and developing high-performing teams.
Excellent communication, presentation, and project management skills.
Strong analytical skills and ability to use data to drive business decisions.
Proficiency in Microsoft Office Suite.

Nice To Haves

Adobe Creative Suite experience.

Responsibilities

Define and manage headwear assortment strategy across sales channels, aligning products with channel needs, customer demand, margin objectives, and brand positioning.
Partner with Product Development, Production, and Planning to build commercially viable and scalable assortments.
Identify category growth opportunities using customer insights, sales analysis, and market trends.
Establish seasonal merchandising vision across headwear brands and sales channels.
Collaborate with Creative Art and Product Development on trend direction, color stories, and product themes; translate brand strategy into product assortments and selling stories.
Ensure consistent headwear representation across catalogs, sales presentations, digital platforms, and customer-facing materials.
Lead headwear launch execution across Destination, Collegiate, Golf, Corporate, Promotional, K-12, CAST, and Amazon channels.
Coordinate launch timing, communications, and execution across departments; partner with Sales leadership on channel strategies, selling tools, product presentations, key-account initiatives, and channel growth opportunities.
Oversee headwear sample strategy and budget for line reviews, trade shows, showrooms, photoshoots, and launches.
Lead headwear decoration direction with Product Development and Creative Art, ensuring approaches align with brand standards, customer expectations, production capabilities, and cost targets.
Partner with Apparel Merchandising on headwear representation at trade shows, concept shops, and brand activations; direct assortment presentation, display standards, sample readiness, and selling tools.
Provide budget input and ROI accountability for headwear-related investments.
Partner with Marketing and Apparel Merchandising on photoshoots and AI-generated content planning; ensure compelling imagery and brand-consistent messaging.
Create headwear product copy and merchandising content for catalogs, digital platforms, and sales materials.
Monitor sales performance by channel, style, color, and category; identify opportunities and risks through sales, inventory, and market-trend analysis.
Partner with Planning to maximize sell-through, improve profitability, and reduce inventory exposure; turn data into assortment and go-to-market recommendations.
Lead and develop the Headwear Merchandising team, setting clear expectations, priorities, and accountability.
Build cross-functional partnerships and drive organizational alignment through communication and project leadership; foster collaboration, ownership, and continuous improvement.
Use AI tools to improve assortment planning, trend analysis, sales insights, and workflow efficiency, and support team adoption of emerging technologies while maintaining commercial rigor and brand integrity.