
Head of Content & Storytelling – Fractional
Good Trouble, Chicago, IL, United States
Are you a bourbon enthusiast and troublemaker? Join our GROWING TEAM at Good Trouble Bourbonand 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
ewsletter (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. #J-18808-Ljbffr
ewsletter (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. #J-18808-Ljbffr