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Good Trouble

Head of Content & Storytelling – Fractional

Chicago, IL, USHead of Department

About This Role

Are you a bourbon enthusiast and troublemaker? Join our GROWING TEAM at Good Trouble Bourbon and help drive sales and brand recognition at our rapidly growing company.

Mission

Turn Good Trouble into a daily, unavoidable cultural presence through powerful storytelling across platforms.

What This Role Really Does

This person ensures:

  • The brand shows up every day, everywhere, with intention
  • The story is felt, not just told

Key Outcomes

  • Build a high\-output content engine (daily/weekly cadence)
  • Scale Dee as a category\-defining founder voice
  • Drive organic reach, engagement, and cultural relevance
  • Create signature content series (Blues, leadership, legacy)

Core Responsibilities

* Own content strategy across:
* + LinkedIn (thought leadership)
+ Instagram (brand \+ lifestyle)
+ Email/newsletter (conversion \+ depth)
+ TikTok (engagement \+ lifestyle)
+ Video (short\-form \+ long\-form)
* Build and manage:
* + Content calendar (90\-day rolling)
+ Creative team (design, video, copy)
* Develop:
* + Campaigns (Trouble in Blues, Pour With Purpose)
+ Founder storytelling platform (“Courage by Design” integration)
* Track and optimize engagement \+ conversion

Ideal Profile

  • Background in:
  • + Media, storytelling, or brand content
  • Has built audience\-driven brands or personalities
  • Understands algorithm \+ emotion \+ narrative
  • Can balance luxury \+ authenticity

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.*