Headwear Designer & Product Developer

Salary Range: $75,000–$80,000 annually, depending on experience

Location: Apopka, FL

Job Type: Full-Time | On-Site

Salary Range: $75,000–$80,000 annually, depending on experience

Relocation Assistance: Available for qualified candidates

For more than two decades, Entertainment Retail Enterprises (ERE) has specialized in the design, development, and distribution of private-label and licensed merchandise for recognized brands and retailers.

As our portfolio continues to grow, we are looking for a creative and experienced Headwear Designer & Product Developer to join our Design & Product Development team.

This role will focus primarily on men's headwear
, with responsibility for designing, developing, and independently managing the headwear category across multiple brands. The ideal candidate combines strong headwear design and graphic design skills with hands-on product development experience and the ability to take ownership of the category from initial concept through production.

• Design and develop seasonal headwear collections, primarily focused on men's outdoor, workwear, lifestyle, and casual markets.
• Independently manage the headwear category across multiple brands, from initial concept through production.
• Research market trends, competitors, fabrics, trims, colors, graphics, and headwear silhouettes to identify new product opportunities.
• Develop seasonal concepts, mood boards, color palettes, and product assortments aligned with each brand's identity and customer.
• Create original graphics, logos, embroidery artwork, patches, and other headwear embellishments.
• Design a variety of headwear styles, including baseball caps, trucker hats, performance caps, snapbacks, beanies, and other seasonal styles.
• Develop detailed CADs, technical packages, artwork files, specifications, and construction details for overseas development teams.
• Select and develop fabrics, trims, closures, patches, embroidery techniques, washes, and other headwear components.
• Manage sample development, review prototypes, and provide clear comments and corrections to factories.
• Evaluate headwear fit, shape, crown construction, brim profiles, proportions, and overall quality.
• Work directly with our China office and overseas factories to resolve design, construction, artwork, and production issues.
• Review and approve lab dips, strike-offs, embroidery samples, trims, pre-production samples, and TOP samples.
• Partner with sourcing and production teams to ensure designs meet target costs, quality standards, and manufacturing requirements.
• Maintain organized development calendars, track sample progress, and proactively follow up on outstanding items.
• Manage multiple brands, collections, and deadlines independently while ensuring timely execution.
• Collaborate with department leadership and cross-functional teams to align headwear assortments with overall brand and business objectives.

• 5+ years of experience in headwear design, accessories design, or apparel design with significant headwear development experience.
• Strong experience designing and developing men's headwear required.
• Strong graphic design skills, including the ability to create original artwork, logos, patches, and embroidery designs.
• Proven ability to independently manage a product category from concept through production.
• Strong understanding of headwear construction, fit, crown shapes, brim profiles, materials, and manufacturing techniques.
• Experience developing a variety of headwear styles, including structured and unstructured caps, trucker hats, performance headwear, and knit beanies.
• Strong knowledge of embroidery, screen printing, heat transfers, woven patches, leather patches, and other decoration techniques.
• Advanced proficiency in…