Head of Thumbnail Strategy and Packing; Remote

Overview

Company Description

We suggest you enter details here.

Role Description

Head of Thumbnail Strategy & Packaging (Fractional) — Florida, Florida (Remote)

The Opportunity

We're not looking for a thumbnail designer. We're looking for a packaging obsessive—someone who has led thumbnail strategy for major You Tube channels and knows exactly what it takes to earn the click at scale.

You'll own thumbnails end-to-end for one of the fastest-growing channels in the AI space. You'll lead a team of designers, build the systems that drive our creative process, and work directly with me (Liam) and our Head of Content to shape how millions of people discover our videos. Here's what makes this different:

You'll be at the cutting edge of AI and content creation. We're building internal AI-powered tools and workflows for thumbnail ideation, testing, and optimization. Your input will directly shape these systems. You'll learn more about applied AI in content creation than anywhere else on the planet.

You'll work with a team that's obsessed with excellence. Our goal is simple: have the best thumbnails in the entire AI and business education space. Not good. The best. That's the standard, and that's what you'll help us achieve.

You'll have real ownership and impact. This isn't a "make what we tell you" role. You'll be leading strategy, pushing creative boundaries, and driving measurable results that shape the channel's growth.

• Research & Ideation:
  Analyze competitor thumbnails across AI, business, and creator education to identify winning patterns
• Translate video concepts and titles into clear, performance-driven thumbnail strategies
• Develop multiple conceptual directions per video and systematize ideation processes

• Design Leadership & Execution:
  Lead and oversee thumbnail designers to produce on-brand, mobile-first thumbnails optimized for CTR
• Build, optimize, and maintain all thumbnail workflows, processes, and systems
• Innovate new formats, structures, and approaches that push beyond current performance
• Ensure quality control across all assets and maintain clear standards across the team

• Collaboration & Iteration:
  Work closely with the Head of Content and directly with Liam on strategy, narrative, and brand alignment
• Iterate thumbnails and workflows based on performance data, feedback, and evolving audience psychology
• Communicate clearly around timelines, revisions, and creative direction

• Operational Excellence:
  Hit deadlines consistently in a fast-paced environment
• Maintain organized files, versioning, and documentation
• Support A/B testing and ongoing optimization to drive measurable results

Must-Have

• Extensive experience leading thumbnail strategy and design for large You Tube channels (not just designing—leading)
• Deep understanding of You Tube psychology: curiosity, clarity, contrast, emotion
• Proven ability to create and implement systems for thumbnail ideation, design, and optimization
• Experience managing and mentoring designers to produce high-CTR thumbnails
• Track record of innovating and pushing creative boundaries
• Organized, reliable, and highly collaborative

Nice-to-Have

• Experience with AI, tech, business, or creator education channels
• Familiarity with A/B testing tools and iterative optimization processes

This is a fractional/part-time position (~20 hours/week initially during system setup, tapering to 10-15 hours/week once workflows are running).

Long-term. High-impact. Direct collaboration with leadership.

• A portfolio of published You Tube thumbnails and/or examples of channels you ve led
• A short Loom video (3-5 minutes) covering:
• 2-3 thumbnails you ve created and the strategic thinking behind them
• One thumbnail from our channel that works - and why
• One from our channel that doesn t - and why