Head of Content & Storytelling - Fractional
207 E. Ohio St., Chicago, IL
Contractor
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:
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The brand shows up every day, everywhere, with intention
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The story is felt, not just told
Key Outcomes
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Build a high-output content engine (daily/weekly cadence)
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Scale Dee as a category-defining founder voice
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Drive organic reach, engagement, and cultural relevance
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Create signature content series (Blues, leadership, legacy)
Core Responsibilities
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Own content strategy across:
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LinkedIn (thought leadership)
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Instagram (brand + lifestyle)
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Email/newsletter (conversion + depth)
- TikTok (engagement + lifestyle)
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Video (short-form + long-form)
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Build and manage:
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Content calendar (90-day rolling)
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Creative team (design, video, copy)
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Develop:
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Campaigns (Trouble in Blues, Pour With Purpose)
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Founder storytelling platform (“Courage by Design” integration)
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Track and optimize engagement + conversion
Ideal Profile
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Background in:
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Media, storytelling, or brand content
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Has built audience-driven brands or personalities
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Understands algorithm + emotion + narrative
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Can balance luxury + authenticity
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