Wholesale Territory Manager - Midwest

Huckberry•Chicago, IL

8d•Hybrid

About The Position

Huckberry is an outdoor lifestyle brand seeking a driven, people-first Wholesale Territory Manager to expand its footprint across the Midwest. This role involves operating at the intersection of sales, education, and brand building, spending significant time in the field managing national accounts, conducting product knowledge sessions, creating visual displays, and identifying new independent accounts. The position is based in Chicago, with a split between a remote home office and Huckberry's local retail store, serving as a base for meetings and market weeks. The role reports to the VP of Wholesale.

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
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.

Nice To Haves

Established relationships within the Midwest specialty or independent retail community is a major plus

Responsibilities

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
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
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

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