Head of Community

About Flightstory and The Diary of a CEO

Flightstory is a media and investment company dedicated to amplifying creators' stories, fostering communities, and backing founders who inspire better lives worldwide. Their flagship show, The Diary of a CEO (DOAC), reaches over 50 million monthly listeners globally. Despite this vast audience, individuals often engage with the content in isolation. Flightstory seeks to build a global community that transforms passive listeners into active members who find connection, shared experiences, and belonging.

Role Purpose

The Head of Community will spearhead the transformation of the DOAC audience into an engaged, vibrant community. This leader will devise and implement strategies, structures, and events – from local meet-ups to global retreats and clubs – that enable members worldwide to interact meaningfully and feel part of a larger collective.

Key Responsibilities

• Develop and implement scalable community-building strategies for DOAC that can be adapted across Flightstory's portfolio.
• Create and manage diverse experiences, including in-person events, running clubs, retreats, and member-led groups that foster connection.
• Design and oversee digital platforms that encourage authentic human interactions through shared stories and support.
• Empower community advocates by providing tools and opportunities for members to contribute to and shape the community's evolution, converting it from a company-run group to a member-owned movement.
• Gather and relay community feedback and stories to inform DOAC content, products, and partnerships, ensuring a responsive feedback loop.
• Monitor and measure community growth with both quantitative data and qualitative narratives demonstrating real impact.
• Innovate by experimenting with new formats and platforms, scaling successful initiatives.

Candidate Competencies

• Proven track record of establishing communities or networks from the ground up.
• Experience planning and executing large-scale, complex events that foster meaningful connections.
• Deep cultural insight to understand the needs and desires of ambitious, curious individuals.
• Ability to translate ideas into enduring systems, routines, and rituals.
• Excellent storytelling skills to clearly and excitingly communicate vision and purpose.
• Competent in leveraging data and member feedback to enhance community engagement.
• Strong sense of ownership and proactive problem-solving in fast-moving environments.

Success Criteria

• Within 6 to 12 months, transition the DOAC audience from disconnected listeners to a thriving community engaged in offline and online gatherings globally.
• Establish meaningful communal rituals and an inclusive culture spanning global cities, from London to Lagos to Los Angeles and beyond.
• Create a replicable community framework that Flightstory uses to convert audiences into participatory communities across all its shows.

Why You’ll Excel

• You operate with a founder's mentality—taking initiative, owning challenges, and building from scratch.
• You balance strategic thinking with practical action, moving quickly to test and validate ideas.
• You are passionate about assembling global communities that make tangible impacts on individuals' lives.
• You derive energy from uniting driven people to connect and support one another.
• You pay attention to both detailed experiences and overarching objectives.
• You thrive in dynamic, fast-paced environments focused on meaningful results.