Chicago Sales/Brand Ambassador
Good Trouble Bourbon, Chicago, IL, United States
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. From the legacy of Chicago blues to the city’s next generation of leaders and creators, Good Trouble brings people together through story, culture, conversation, and exceptional bourbon. Our activations are not traditional tastings. They are experiences. Our mission is simple: Make Good Trouble Bourbon Chicago’s Bourbon.
The Role We are seeking charismatic Cultural Hosts and Storytelling Ambassadors to represent Good Trouble Bourbon at tastings, cultural events, retail activations, and private gatherings. This role is ideal for people who naturally bring energy, warmth, and connection into a room. You will not simply pour samples. You will host experiences, share the story behind the brand, and create memorable moments that invite people into the Good Trouble movement.
What You Will Do
Host Experiences: Lead engaging tasting experiences at select Chicago retailers, bars, restaurants, and cultural events.
Tell the Brand Story: Share the inspiration and meaning behind Good Trouble Bourbon in a compelling and authentic way.
Engage with Guests: Approach guests confidently, spark conversation, and create a welcoming environment.
Represent the Brand: Maintain a polished, professional presence that reflects the premium positioning of the brand.
Build Community: Encourage guests to connect with the Good Trouble movement through events, social channels, and word‑of‑mouth.
Who You Are You are someone who naturally brings people together. You may be a:
bartender or hospitality professional
artist or creative
event host or promoter
community builder
entrepreneur or storyteller
You are comfortable approaching strangers, starting conversations, and making people feel welcome. You understand that the best experiences come from authentic connection and storytelling.
Qualifications Preferred experience includes:
hospitality or bartending
experiential marketing or brand representation
event hosting
retail or hospitality sales
Requirements:
age 21+
availability for evenings and weekends
reliable transportation within Chicago
confident communicator
professional appearance
What Makes This Different This is not a typical brand ambassador role. You will represent a brand that celebrates culture, courage, leadership, and community. You will help build a movement centered around builders, dreamers, and people willing to stir things up for the better.
Compensation
Competitive
Event bonuses
Brand merchandise
Opportunities for leadership within the Good Trouble network
To Apply Please include:
A short introduction about yourself
Relevant experience
A brief response to these questions: “What does the phrase 'Good Trouble' mean to you?” “If you were introducing Good Trouble Bourbon to a room full of Chicago creatives and leaders, what would you say?”
#J-18808-Ljbffr
The Role We are seeking charismatic Cultural Hosts and Storytelling Ambassadors to represent Good Trouble Bourbon at tastings, cultural events, retail activations, and private gatherings. This role is ideal for people who naturally bring energy, warmth, and connection into a room. You will not simply pour samples. You will host experiences, share the story behind the brand, and create memorable moments that invite people into the Good Trouble movement.
What You Will Do
Host Experiences: Lead engaging tasting experiences at select Chicago retailers, bars, restaurants, and cultural events.
Tell the Brand Story: Share the inspiration and meaning behind Good Trouble Bourbon in a compelling and authentic way.
Engage with Guests: Approach guests confidently, spark conversation, and create a welcoming environment.
Represent the Brand: Maintain a polished, professional presence that reflects the premium positioning of the brand.
Build Community: Encourage guests to connect with the Good Trouble movement through events, social channels, and word‑of‑mouth.
Who You Are You are someone who naturally brings people together. You may be a:
bartender or hospitality professional
artist or creative
event host or promoter
community builder
entrepreneur or storyteller
You are comfortable approaching strangers, starting conversations, and making people feel welcome. You understand that the best experiences come from authentic connection and storytelling.
Qualifications Preferred experience includes:
hospitality or bartending
experiential marketing or brand representation
event hosting
retail or hospitality sales
Requirements:
age 21+
availability for evenings and weekends
reliable transportation within Chicago
confident communicator
professional appearance
What Makes This Different This is not a typical brand ambassador role. You will represent a brand that celebrates culture, courage, leadership, and community. You will help build a movement centered around builders, dreamers, and people willing to stir things up for the better.
Compensation
Competitive
Event bonuses
Brand merchandise
Opportunities for leadership within the Good Trouble network
To Apply Please include:
A short introduction about yourself
Relevant experience
A brief response to these questions: “What does the phrase 'Good Trouble' mean to you?” “If you were introducing Good Trouble Bourbon to a room full of Chicago creatives and leaders, what would you say?”
#J-18808-Ljbffr