Director Headwear Merchandising

Job Type Full-time Description Director Headwear Merchandising Remote | Full-Time About L2 Brands L2 Brands represents a family of established industry-leading brands - League, Legacy, Ouray, Locale, and Wild Tribute - dedicated to delivering premium apparel, headwear, and licensed consumer merchandise. Each brand carries its own distinct identity while contributing to a cohesive, growth-driven enterprise with deep roots and a clear vision for the future. Our growth is powered by authentic customer relationships, product innovation that anticipates market trends, and an organizational culture that values collaboration and continuous improvement. The Opportunity For an experienced merchandising leader with a passion for product and brand storytelling, L2 Brands offers the opportunity to shape the future of our headwear business across multiple brands and sales channels. The Director Headwear Merchandising will lead assortment strategy, seasonal direction, and go-to-market execution for the Legacy and Ouray headwear portfolios. This role serves as the commercial leader for headwear, ensuring the right products are developed, positioned, and launched to drive growth, profitability, and long-term brand strength. What You'll Be Responsible For: 1. Assortment Strategy & Line Planning Define and manage the headwear assortment strategy across all sales channels. Ensure products align with channel needs, customer demand, margin objectives, and long-term brand positioning. Partner with Product Development, Production, and Planning to build commercially viable and scalable assortments. Identify category growth opportunities through customer insights, sales analysis, and market trends. 2. Seasonal Merchandising Vision & Brand Direction Establish the 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 compelling product assortments and selling stories. Ensure consistency across catalogs, sales presentations, digital platforms, and customer-facing materials. 3. Product Launch & Channel Execution Lead headwear launch execution across Destination, Collegiate, Golf, Corporate, Promotional, K-12, CAST, and Amazon channels. Coordinate launch timing, communication, and execution across departments. Partner with Sales leadership to develop channel-specific strategies, selling tools, and product presentations. Support key account initiatives and channel growth opportunities. 4. Sample & Decoration Oversee the headwear sample strategy and budget across line reviews, trade shows, showrooms, photoshoots, and launches. Lead headwear decoration direction in partnership with Product Development and Creative Art across existing and emerging applications and techniques. Ensure decoration strategies align with brand standards, customer expectations, production capabilities, and cost targets. Collaborate across Product Development, Creative Art, Production, and Sales to bring concepts to market successfully. 5. Trade Shows & Brand Activations Partner with Apparel Merchandising to ensure headwear is effectively represented 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. 6. Photoshoot & Content Direction Partner with Marketing and Apparel Merchandising on photoshoots and AI-generated content planning. Ensure headwear products are represented with compelling imagery and brand-consistent messaging. Responsible for headwear product copy and merchandising content across catalogs, digital platforms, and sales materials. 7. Business Performance & Merchandising Analytics Monitor sales performance by channel, style, color, and category. Identify opportunities and risks through analysis of sales, inventory, and market trends. Partner with Planning to maximize sell-through, improve profitability, and reduce inventory exposure. Translate data into actionable assortment and go-to-market recommendations. 8. Team Leadership & Cross-Functional Collaboration Lead and develop the Headwear Merchandising team with clear expectations, priorities, and accountability. Build strong partnerships across Product Development, Creative Art, Marketing, Planning, Sales, and Training. Drive organizational alignment through effective communication and project leadership. Foster a culture of collaboration, ownership, and continuous improvement. 9. AI-Enabled Merchandising Leverage AI tools to improve assortment planning, trend analysis, sales insights, and workflow efficiency. Explore innovative approaches that enhance speed, accuracy, and decision-making. Support team adoption of emerging technologies while maintaining commercial rigor and brand integrity. Who Thrives Here You are a product-centric leader who combines creativity with commercial discipline. You have a keen eye for trends, a deep understanding of what motivates buyers, and the confidence to make strategic decisions that drive results. You communicate clearly, build trust quickly, and thrive in a collaborative environment where accountability and execution matter. You enjoy working across functions, solving complex business challenges, and creating products and experiences that strengthen brands and deliver growth. What to Expect Full-time, salaried position based in a professional office environment. Approximately 50% travel for trade shows, customer meetings, brand activations, and team collaboration. Reports to the Chief Experience Officer. Opportunity to influence the strategic direction of a growing multi-brand organization with strong market presence and significant growth potential. Requirements What We're Looking For 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 with the ability to balance customer needs, brand direction, and financial performance. Background 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 with the ability to leverage data to drive business decisions. Proficiency in Microsoft Office Suite; Adobe Creative Suite experience is a plus. L2 Brands