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Robinson Hill is seeking a Chicago Market Sales Manager to drive growth for Good Trouble Bourbon across various venues in Chicago. This role involves building relationships with retailers and distributor partners while leading a Cultural Host team to deliver brand experiences.
The ideal candidate will have spirits industry experience, account management knowledge, and a strong network within Chicago's hospitality scene. The position offers competitive compensation and the unique opportunity to grow a leading bourbon brand in the cultural landscape.
Good Trouble Bourbon
Chicago Market Sales Manager/Market Leader
Chicago | Full Time | Leadership Role
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.
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.
Lead the growth of Good Trouble Bourbon throughout Chicago and surrounding markets. Build strong relationships with retailers, bars, restaurants, and cultural venues.
Work closely with distributor partners to drive:
Ensure Good Trouble receives strong attention within the distributor portfolio.
Develop strategic placements in high-impact accounts including:
Drive strong relationships with key Chicago retailers including:
Recruit, train, and manage the Good Trouble Cultural Host team. Ensure brand ambassadors deliver exceptional experiences that translate into sales.
Partner with leadership to execute brand activations including:
Monitor and report on:
The ideal candidate is a relationship-driven market builder who thrives in entrepreneurial environments. You are equally comfortable:
Preferred experience includes:
Strong marketing acumen and network within the Chicago hospitality community are highly valued.
The successful candidate will demonstrate:
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.
Please include: a short introduction, relevant experience, your perspective on how to build a spirits brand in Chicago.