Nathan Wrigley speaks with Jonathan Desrosiers, a principal software engineer at Bluehost and long-time WordPress core committer sponsored through Five for the Future, about making releases into community moments, improving contributor onboarding, and rebuilding engagement after COVID.
The pair explore an idea Jonathan has been promoting: intentionally timing major WordPress releases to coincide with flagship community events such as WordCamp Asia, WordCamp Europe, WordCamp US, and State of the Word. The notion started somewhat accidentally when a release landed during State of the Word and was announced live, creating an energized, visible moment for contributors. The aim is to merge the technical milestone of a release with the human energy of community gatherings so contributions are celebrated and more people can witness the result of volunteer work.
They acknowledge the practical challenges. Event dates are driven by budgets, venues, local holidays, and travel windows, so they cannot be dictated by the release calendar. Conversely, release planning must respect global calendars — religious holidays and national breaks affect contributor availability. To address this, teams build release squads with people spread across time zones so someone is available to handle issues if parts of the world are offline. The squads try to provide “global coverage” during critical windows.
Jonathan and Nathan talk about the theatrical pull of synchronized launches — the metaphorical “big red button” — and whether that fanfare can raise awareness without becoming mere marketing. For Jonathan, the goal is to make releases more visible in a way that celebrates community effort and draws people in, rather than transforming releases into promotional stunts. They also discuss the benefits of more frequent, smaller releases—faster feedback cycles and shorter time between contribution and deployment—while recognizing the constraints of WordPress’s scale and strict backward-compatibility commitments.
A recurring topic is awareness and onboarding. Because auto-updates make upgrades seamless, many users never notice releases. That invisibility is a sign of quality but also a missed opportunity to teach people about new features. Jonathan suggests surfacing changes in more user-facing ways: dashboard widgets, Learn WordPress links, pre-release communications, and testing opportunities. He describes a feature-branch approach that would allow discrete features to be showcased and tested independently, but admits that editor architecture and interdependencies make that technically challenging.
The data is encouraging: adoption of recent major releases has accelerated. For example, WordPress 6.9 reached 50% of sites in ten days, faster than earlier versions — a sign of growing confidence in updates and effective auto-update behavior.
They turn to community health. COVID disrupted the usual mentorship and succession pipelines: many meetup and WordCamp leaders stepped back, attendance dipped in some regions, and local groups lost momentum. Rebuilding won’t be one-size-fits-all. APAC, for instance, has seen strong growth and new communities, while the US and Europe need different strategies to re-energize local groups.
Successful recovery efforts include education, mentorship programs, WP Credits, and contributor mentorship that intentionally moves people from mentee to mentor and into leadership roles. Jonathan stresses that attracting newcomers isn’t enough; projects must offer clear pathways, meaningful tasks, and ongoing support so people remain engaged after initial events like Contributor Day. Release parties and in-person testing run during events can act as pilot programs for onboarding and for experimenting with release processes.
Engaging younger people raised on closed platforms is another priority. To bring them into open source, WordPress must make contribution relevant, practical, and career-friendly — showing how involvement can lead to real work, products, and services. Education initiatives aimed at schools and universities show promise, but those efforts must be paired with activation support so interested students don’t flounder.
AI entered the conversation as a major shaping force. Jonathan views AI as an empowering tool that can lower barriers: it can summarize documentation, help people prototype without deep technical skills, and make experimentation less intimidating. This could help revive personal websites, blogging, and ownership of online identity outside walled gardens. He also cautions that AI can churn out low-quality content, and that building secure, accessible, scalable solutions will still need skilled contributors.
Jonathan and Nathan agree AI may encourage more people to try building things themselves — online and offline — and that WordPress stands to benefit if it provides the right tooling, documentation, and clear newcomer pathways. Jonathan closes by reaffirming his focus on contributor experience: automating processes, clarifying tasks, strengthening mentorship, and creating more chances for contributors to see their work reach production. He invites listeners to join events and Contributor Days, and points to jonathandesrosiers.com and the WordPress.org Slack as ways to connect.
Nathan expresses hope that synchronized releases, improved onboarding, active Meetups, education, and AI-driven empowerment can revive community involvement so WordPress remains vibrant and relevant in the decade ahead.