Home Based Wholesale Footwear Jobs in Chicago, IL

Huckberry is an outdoor lifestyle brand built on the belief that adventure should be accessible, stylish, and built to last. We curate the world's best gear, apparel, and footwear-and now we're bringing that same obsession with quality and craft to wholesale retail partners across the country.  Our Wholesale team is growing, and we need a driven, people-first Territory Manager to expand our footprint and elevate the Huckberry experience at every single point of sale.

This isn't an order-writing desk job. As the face of Huckberry across the Midwest, you'll operate at the high-octane intersection of sales, education, and brand building. You will spend significant time in the field managing national accounts, running product knowledge sessions, building killer visual displays, and scouting the next great independent accounts to join the family.  Based in Chicago, you'll split time between your remote home office and Huckberry's local retail store-your basecamp for account meetings and market weeks.

In this position, you will report to the VP of Wholesale.

• Account Management & Visual Merchandising
• Act as the primary field contact for national and regional accounts, executing strategic call cycles using an A/B/C prioritization framework
• Partner with buyers to plan and execute seasonal floor sets, fixture updates, and strict Huckberry visual merchandising standards
• Analyze sell-through data to flag risks early and unlock high-impact replenishment opportunities
• Brand Evangelism & Product Training
• Deliver engaging, brand-consistent product knowledge (PK) training sessions to retail staffs, tailoring your approach to account sizes and product categories
• Master Huckberry's product stories, materials, and use cases to build authentic enthusiasm with store crews and managers
• Territory Growth & Operations
• Prospect, pitch, and open promising new independent and regional wholesale accounts across the Midwest retail landscape
• Collaborate directly with the Director of Wholesale to set territory-specific targets and develop strategies to smash them
• Conceptualize and execute high-energy in-store events, trunk shows, and local activations that drive traffic and clear ROI
• Own weekly CRM field reporting, territory plans, quarterly business reviews, and travel budget efficiency

Requirements

• 3-5+ years of experience in field sales, territory management, or retail leadership-ideally within the apparel, footwear, outdoor, or lifestyle sectors
• A proven track record of opening new accounts, managing pipeline accounts, and driving territory sales growth
• Experience running product training for retail staff or working within national account field structures
• Established relationships within the Midwest specialty or independent retail community is a major plus

Skills & Competencies

• Natural Connector: Instantly builds relationships with everyone from sales floor associates to corporate regional buyers
• Dynamic Presenter: Comfortable commanding a room of 20 retail staff or leading a 1-on-1 pitch with a boutique owner
• Retail Literacy: Deep understanding of floor merchandising, sell-through dynamics, and managing a territory like your own business
• Road-Ready: Valid driver's license and a genuine willingness to travel extensively (50-70%) across the territory

• Tech Savvy: Proficient in CRM platforms (Salesforce, HubSpot, or similar) and Google Workspace or Microsoft Office.

Benefits

• Competitive base salary + performance-based bonus / commission structure
• Car allowance or mileage reimbursement + full travel expense coverage for the open road
• Medical, Dental, Vision benefits
• 401(k) and employer match
• Annual Huckberry shopping credits
• Paid Sabbatical leave at 4 years
• Mental health resources
• Paid Parental Leave
• Paid Vacation & Paid Sick Leave
• Volunteer Time Off
• Generous employee discount
• WFH flexibility
• Annual offsites

Huckberry is the ultimate one-stop men's shop for discovering the best gear and threads. Over a million guys trust us as their go-to resource for their closet, adventure inspiration, and a whole lot more. We were named one of IAB's most disruptive consumer brands, and we've collaborated with everyone from Matthew McConaughey and Leon Bridges to brands like Lululemon, Tacoma, and Coors. We look forward to meeting you.

Want to get to know us better? Check out our:

• Journal: http://huckberry.com/blog
• Youtube: https://www.youtube.com/@Huckberryco
• Instagram: http://instagram.com/huckberry

Huckberry encourages candidates of all different backgrounds and identities to apply. We are always eager to further diversify our company, and we are committed to providing an inclusive environment of mutual respect where all can flourish. All of our employment decisions are based solely on merit and business need.