Director of Content Strategy

Matthew Berry's Fantasy Life

2h

About The Position

The Director of Content Strategy is responsible for defining and executing Fantasy Life’s company-wide content strategy, ensuring content drives growth, engagement, and revenue while remaining scalable, disciplined, and performance-driven. This role owns content performance and manages the content operating budget, ensuring resources are allocated efficiently to support sustainable growth and profitability.
The Director of Content Strategy oversees content strategy across written, premium, social, video, and Guillotine Leagues content. They are accountable for KPIs, sponsorship integration, and distribution strategy, and manage the Video team from a strategic and performance standpoint, while dedicated video leadership oversees day-to-day production and execution.
This is a senior leadership role designed to bring focus, structure, and accountability to how content is created, distributed, and monetized across the business.

Requirements

• Senior content leader with experience scaling digital media or creator-led brands.
• Strong understanding of content monetization and sponsorship integration.
• Proven ability to manage teams against clear KPIs.
• Comfortable operating at the intersection of content, revenue, and analytics.
• Strategic, decisive, and execution-oriented.

Responsibilities

• Own the end-to-end content strategy across Fantasy Life and Guillotine Leagues.
• Define content priorities, franchises, and formats aligned with business goals.
• Ensure all major content initiatives are built around full-time creators and scalable formats.
• Maintain consistent voice, tone, and quality standards across all branded content.
• Oversee Guillotine Leagues content strategy with a focus on: Growing the platform Increasing user engagement Enhancing the overall user experience through content
• Own content KPIs across all formats and platforms, including: Engagement and audience growth Conversion to premium Product Sponsorship and branded content performance Platform-specific benchmarks (written, social, video)
• Use performance data to guide content decisions, prioritization, and investment.
• Establish clear expectations and accountability for teams and creators.
• Oversee the strategy and execution of branded and sponsorable content.
• Partner closely with Sales to ensure content supports advertiser and partner objectives.
• Ensure integrations are thoughtful, high-quality, and scalable.
• Balance monetization opportunities with editorial integrity and audience trust.
• Ensure branded content has a distinct look, feel, and promotion strategy.
• Provide strategic leadership and performance oversight for video content.
• Set expectations for: Output and cadence Platform-first optimization Audience growth and engagement Alignment with content franchises and sponsorship goals
• Partner with the Video Lead, who owns production, showsheets, and execution.
• Ensure video content supports broader business objectives, including content licensing.
• Own how content is packaged, prioritized, and distributed across platforms.
• Partner with Social and Marketing to ensure content reaches the right audience in the right format.
• Ensure platform-specific optimization across social, video, and owned channels.
• Treat distribution as a core part of content success—not an afterthought.
• Own the content operating budget in partnership with Finance.
• Make tradeoff decisions to balance quality, scale, and profitability.
• Ensure content strategy improves margins and efficiency over time.
• Oversee contractor usage and resource allocation to support sustainable growth.
• Lead and manage full-time writers, editors, and content support staff.
• Establish clear output expectations for in-season and offseason production.
• Guide contractor strategy and usage, including decisions around retention and replacement.
• Improve processes to eliminate bottlenecks and competing deadlines.
• Lead organizational change required to improve focus and performance.
• Work closely with Sales on sponsorship strategy and promotion Marketing and Social on distribution and growth Product to align content with tools, features, and user behavior Analytics to ensure performance clarity and accountability
• Serve as the connective tissue between content creation and business outcomes.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed