Market Sales Manager

Good Trouble•Chicago, IL

10h

About The Position

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. 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. 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. 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 and opening new retail accounts. Inspired by legendary troublemakers like civil rights icon John Lewis who urged us to get into “good trouble, necessary trouble”, Good Trouble bourbon is an award-winning Kentucky Straight Bourbon Whiskey crafted at the historic DSPY-KY-10, the 10th oldest bourbon distillery in Kentucky, dating back to 1885. Good Trouble Bourbon is committed to creating a diverse environment and is proud to provide equal employment opportunities in all employment practices. We will honor your experiences, perspectives, and unique identity.

Requirements

Strong relationship-building ability
Entrepreneurial mindset
Cultural awareness and curiosity
Disciplined sales execution

Nice To Haves

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.

Responsibilities

Market Leadership
Distributor Partnership
Work closely with distributor partners to ensure Good Trouble receives strong attention within the distributor portfolio to drive account placements, sales velocity and brand visibility.
Retail & On-Premise Expansion
Develop strategic placements in high-impact accounts including premium restaurants, cocktail bars, retail liquor stores and cultural venues
Drive strong relationships with key Chicago retailers
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 and community gatherings.
Performance Tracking
Monitor and report on account growth, retail velocity, event performance and market expansion opportunities.