Good Trouble Bourbon Chicago Market Sales Manager/Market Leader Chicago | Full Time | Leadership Role About 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 placements • sales velocity • brand visibility Ensure Good Trouble receives strong attention within the distributor portfolio. Retail & On-Premise Expansion Develop strategic placements in high-impact accounts including: • premium restaurants • cocktail bars • retail liquor stores • cultural 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: • tastings • cultural events • hospitality partnerships • community gatherings Performance Tracking Monitor and report on: • account growth • retail velocity • event performance • market 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 bartenders • presenting to distributor leadership • hosting brand events; creating and executing creative in-market activations • opening new retail accounts Experience Preferred experience includes: • spirits industry sales • distributor portfolio management • hospitality or beverage experience • account 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 ability • entrepreneurial mindset • cultural awareness and curiosity • exceptional communication skills • disciplined sales execution What Makes This Role Unique This 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 Apply Please include: • a short introduction • relevant experience • your perspective on how to build a spirits brand in Chicago