Job Description
Good Trouble Bourbon
Chicago Market Sales Manager/Market Leader:
  • Chicago | Full Time | Leadership RoleAbout Good Trouble Bourbon
  • Good Trouble Bourbon is more than a spirit. It is a cultural platform.
  • Inspired by the call to “get into good trouble,” the brand celebrates the builders, dreamers, and people willing to challenge the status quo.
  • Rooted in the legacy of Chicago blues and the city’s rich cultural history, Good Trouble Bourbon brings people together through story, music, leadership, and community.
  • Our mission is bold:
  • Make Good Trouble Bourbon Chicago’s Bourbon.
  • To achieve this, we are building a leadership team that can grow the brand through culture, relationships, and strategic distribution.
Role Overview: We are seeking a Chicago Market Sales Manager to lead the growth of Good Trouble Bourbon across retail, hospitality, and cultural venues. This is not a traditional spirits sales role. The right leader will combine sales execution, cultural intelligence, and entrepreneurial drive to establish Good Trouble as a leading premium bourbon brand in Chicago. You will oversee distribution relationships, retail performance, ambassador teams, and strategic cultural activations.
Key Responsibilities
Market Leadership: Lead the growth of Good Trouble Bourbon throughout Chicago and surrounding markets. Build strong relationships with retailers, bars, restaurants, and cultural venues.
Distributor Partnership: Work closely with distributor partners to drive:account placementssales velocitybrand visibility Ensure Good Trouble receives strong attention within the distributor portfolio.
Retail & On-Premise Expansion: Develop strategic placements in high-impact accounts including:premium restaurantscocktail barsretail liquor storescultural venues Drive strong relationships with key Chicago retailers including: • Binny's Beverage Depot and other leading accounts.
Ambassador Team Leadership: Recruit, train, and manage the Good Trouble Cultural Host team. Ensure brand ambassadors deliver exceptional experiences that translate into sales.
Cultural Activation Support:
  • Partner with leadership to execute brand activations including:tastingscultural eventshospitality partnershipscommunity gatherings
  • Performance Tracking
  • Monitor and report on:account growthretail velocityevent performancemarket expansion opportunities
Ideal Candidate: The ideal candidate is a relationship-driven market builder who thrives in entrepreneurial environments. You are equally comfortable: • building relationships with bartenderspresenting to distributor leadershiphosting brand events; creating and executing creative in-market activationsopening new retail accounts Experience
Preferred experience includes: spirits industry salesdistributor portfolio managementhospitality or beverage experienceaccount management in Chicago Strong marketing acumen and network withing the Chicago hospitality community are highly valued.
Skills & Attributes:
  • The successful candidate will demonstrate:strong relationship-building abilityentrepreneurial mindsetcultural awareness and curiosityexceptional communication skillsdisciplined sales execution
  • What Makes This Role UniqueThis is an opportunity to help build Chicago’s bourbon brand.
  • You will play a central role in growing a company that sits at the intersection of culture, music, leadership, and premium spirits.
Compensation Competitive base salary Performance-based bonuses Opportunity to grow into regional leadership roles Participation in building a nationally recognized brand To ApplyPlease include:a short introductionrelevant experienceyour perspective on how to build a spirits brand in Chicago

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Level

Senior L5

Location

Chicago, IL

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Sales Managers

Industry

Distilleries

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