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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

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