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
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Own content strategy across:
- LinkedIn (thought leadership)
- Instagram (brand + lifestyle)
- Email/newsletter (conversion + depth)
- TikTok (engagement + lifestyle)
- Video (short-form + long-form)
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Build and manage:
- Content calendar (90-day rolling)
- Creative team (design, video, copy)
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Develop:
- Campaigns (Trouble in Blues, Pour With Purpose)
- Founder storytelling platform (“Courage by Design” integration)
- Track and optimize engagement + conversion
Ideal Profile
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Background in:
- Media, storytelling, or brand content
- Has built audience-driven brands or personalities
- Understands algorithm + emotion + narrative
- Can balance luxury + authenticity