Head of Packaging, The Diary Of A CEO

FlightStory•Los Angeles, CA

85d•Onsite

About The Position

This role is responsible for owning and executing The Diary Of A CEO's (DOAC) packaging strategy across all platforms, including YouTube, Spotify, audio/RSS, and emerging platforms. The goal is to optimize each episode for maximum performance by focusing on titles, thumbnails, descriptions, and metadata. The Head of Packaging will drive experimentation with a data-driven approach to increase click-through rates and browse impression share, translating performance data into actionable insights that compound reach and retention. A key aspect of this role is to continuously innovate and elevate the packaging strategy to expand DOAC's global reach while rigorously protecting the brand's integrity, voice, and editorial standards.

Requirements

A track record of measurably improving CTR and/or retention on a high-performing YouTube channel.
Deep, current knowledge of YouTube's algorithm, Browse/search/Shorts mechanics, and packaging best practices.
Experience running structured A/B testing programs (e.g. YouTube's native testing tools or equivalent platform testing).
Strong writer with sharp instincts for psychology, curiosity, and audience behavior.
Comfortable working in a fast-paced, in-person environment where speed, iteration, and editorial judgment all matter equally.
Packaging craft: A proven eye for what makes a thumbnail and title work.
Integrity and judgement: Brings intelligence and depth of knowledge to every decision to fiercely protect the brand and reputation of The Diary Of A CEO.
Analytical mindset: Fluent in reading CTR, retention, and impression data, and translating it into clear packaging decisions.
Copywriting & visual instinct: Able to write and direct high-impact titles and thumbnails, and to brief designers effectively.
Testing discipline: Structured, rigorous approach to experimentation with hypotheses, clean test design, and honest reads of results.
Cross-functional collaboration: Works fluidly with editorial, design, production, and leadership to keep packaging moving at speed.
AI fluency: Treats AI as a force multiplier, not a shortcut, and uses it daily to increase output, quality, and speed of learning.
Execution excellence: Highly organized and relentless about turnaround time without cutting corners on quality.

Responsibilities

Lead the end-to-end packaging workflow for every episode: title development, thumbnail concepting and design direction, descriptions, tags, and metadata.
Develop a data-driven process to identify top-tier packaging candidates for every episode.
Design and execute YouTube A/B tests to properly maximize episode performance.
Apply and evolve DOAC's packaging frameworks and codify new findings into the playbook.
Protect the DOAC brand, voice and editorial integrity in every packaging decision.
Own and evolve DOAC's audio packaging (titles, descriptions, and metadata across Spotify, Apple Podcasts, and other platforms) adapting strategy to how audio audiences discover and choose episodes.
Maintain rigorous records and translate historical data into forward-looking packaging recommendations.
Coordinate closely with editorial, production, and design to keep packaging turnaround fast without sacrificing quality.
Track and report on packaging performance (CTR, retention, Browse share) with clear, data-backed narratives for leadership.
Feed packaging and performance insights back into the editorial and booking teams so what gets made is informed by what packages and performs.
Ensure titles, descriptions, and metadata are optimized and consistent across YouTube, audio platforms, and downstream distribution (clips, social, etc.).
Run a systematic back catalog optimization program identifying high-potential library episodes, re-testing titles and thumbnails, and refreshing metadata to capture new search and Browse demand.
Stay ahead of YouTube algorithm changes, platform best practices, and competitor packaging strategy.