
Head of Content & Storytelling - Fractional
Robinson Hill, Chicago, IL, United States
Head of Content & Storytelling
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
#J-18808-Ljbffr
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
#J-18808-Ljbffr