Regional Independent Outside Sales Representative (1099) Part time

Job Overview

We are seeking an experienced, highly connected Regional Independent Outside Sales Representative to represent and expand the Trafalgar accessory line across premier independent men’s specialty stores, haberdashers, and boutique retailers.

This is a 100% commission-based, 1099 independent contractor opportunity. The ideal candidate will be an established multi-line road representative with an active, loyal book of retail buyer relationships, current non-competing lines that naturally pair with luxury accessories, and direct working experience conducting wholesale order management through NuORDER.

Responsibilities

• Drive Wholesale Distribution: Open new, qualified independent specialty store accounts while nurturing and growing replenishment volume in existing brand accounts across the designated territory.
• Line Presentations & Merchandising: Present seasonal collections, classic core assortments, and replenishment programs via in-person retailer visits, trunk shows, regional trade markets, and virtual line reviews.
• Digital Order Writing & Management: Efficiently build custom presentations, draft proposals, create linesheets, and submit wholesale purchase orders directly through NuORDER.
• Order Facilitation & Account Maintenance: Secure initial orders, monitor sell-through, and promote reorder programs utilizing our digital B2B catalog.
• Product Knowledge: Educate retail sales staff and buyers on Trafalgar craftsmanship, leather sourcing, sizing, and styling to maximize floor sell-through.
• Market Feedback: Provide timely regional feedback regarding competitive activity, retail trends, and merchant needs.

Requirements

• B2B Platform Proficiency: Hands-on proficiency with NuORDER is required. Must be comfortable writing wholesale orders, navigating digital linesheets, building customized buyer carts, and managing territory account lists within the platform.
• Existing Network: Proven track record with a current, active roster of independent men’s specialty stores, custom clothiers, and upscale boutiques within the territory.
• Complementary Line Card: Must already carry reputable, non-competing wholesale apparel or footwear lines (e.g., custom/tailored clothing, fine dress shirts, luxury sportswear, or footwear) that cater to the same retail buyer demographic.
• Industry Experience: Minimum 3–5+ years of outside wholesale sales experience in men’s tailored clothing, sportswear, or luxury accessories.
• Self-Motivated & Tech-Savvy: Strong entrepreneurial mindset, self-starter initiative, and comfort using modern mobile and cloud-based wholesale tools on the road (iPad/laptop).
• Mobility: Valid driver’s license, reliable transportation, self-insured and willingness to travel extensively throughout the regional territory as needed.

Pay: $20,000.00 - $80,000.00 per year

Application Question(s):

• Do you currently have an active customer base of independent menswear stores and if so, how many stores are you currently selling?
• What brand (s) of men's apparel, accessories do you currently represent and sell to your accounts?
• What state(s) or region(s) are you available to cover?

Experience:

• Outside sales: 2 years (Required)

Work Location: Remote