Good Trouble Bourbon

Cultural Host & Storytelling Ambassador

Chicago | Part-Time | Experiential 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.

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:

1. A short introduction about yourself

2. Relevant experience

3. 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?