Devin Walker joins the Jukebox Podcast to discuss his new role at Automattic as Artistic Director (head) of Jetpack. With 16 years in WordPress—co‑founding GiveWP, creating WP Rollback, and working across brands like iThemes, Kadence, LearnDash, and The Events Calendar—Devin moved from Liquid Web to Automattic to take on the broad and often divisive Jetpack product.
Why Jetpack?
Devin weighed starting another independent product versus joining Automattic. He chose Jetpack because of the opportunity for impact at scale and the chance to work inside a company he respected. He acknowledges Jetpack’s reputation as a jack‑of‑all‑trades: it offers stats, backups, security, performance tools, sharing, forms, VideoPress, SEO basics, and more. Many of these features were innovative when launched, but third‑party specialists have since raised the bar. Devin’s goal is not to make Jetpack the deepest tool in every niche but to refocus and elevate core capabilities so Jetpack meets the needs of the vast majority of users.
Scope and approach
Automattic has shifted structure from functional silos to a more matrixed organization. Teams across .com, Jetpack, and other products now share architecture and design resources, enabling better collaboration—especially important for shared services and for bringing .com features to self‑hosted WordPress via Jetpack. Devin is leading major upgrades (notably forms), working with top engineers, and prioritizing where to invest effort.
He explains the tradeoffs: Jetpack can’t outcompete every single focused third‑party product on every feature. Instead, the focus is to make Jetpack excellent for the 95–98% of users who need dependable, straightforward features. For the small subset requiring extreme specialization, third‑party solutions will remain appropriate.
User experience and simplification
Devin stresses Jetpack’s complexity and confusing UI as primary areas for improvement. Users can discover multiple places to toggle features, face confusing connection flows, and encounter inconsistent behaviour across themes and block vs classic setups. These issues drive negative reviews—mainly caused by breakages and lack of support. With roughly 4 million core installs, changes must be careful, but improving onboarding, consolidating toggles, clarifying navigation, and reducing surprises are immediate priorities.
He’s adopting Jobs‑to‑Be‑Done thinking: understand what users are trying to accomplish and design flows that deliver that outcome. The aim is to make Jetpack the tool that gets novices to a credible, well‑functioning site quickly—an integrated, polished “strap‑on” that complements WordPress rather than feels like a patchwork of disparate modules.
Product cadence and risk
Jetpack ships monthly and touches massive parts of Automattic’s product ecosystem. That scale requires caution to avoid regressions, but Devin also wants to balance caution with purposeful, visible progress. Recent improvements to the connect/onboarding flow are an example of changes that increased successful connections without massive risk. The plan is to follow user feedback and roll changes deliberately while being more aggressive in cleaning up evident UX debt.
AI: current and future
AI is a major focus. Devin returned from demos with the Automattic AI engineering team and describes Jetpack’s existing AI features—automatic excerpt and featured image generation—as only the beginning. Automattic has a significant investment (50+ engineers) and aims to bring .com AI benefits to self‑hosted sites through Jetpack. The vision is for Jetpack to be a “content companion” that helps inside and outside the editor: assisting with post content, metadata, block creation, visitor engagement, conversion prompts, and form flow. Telex (Automattic’s block generation tool) is highlighted as an exciting direction—imagine prompting Jetpack to create a custom block on demand and seamlessly managing plugin code behind it. Devin foresees AI as the glue that helps disparate Jetpack features work together and integrate tightly with WordPress Core and the Abilities API.
Marketing and perception
Devin identifies marketing as another underleveraged area. Jetpack historically benefited from Automattic’s brand and early market position, but the ecosystem now has many focused competitors with strong marketing. He wants to improve Jetpack’s public narrative, polishing the website, increasing transparency about what Jetpack does, and amplifying internal P2 posts and demos to public audiences. He’s observed a relatively low marketer‑to‑product ratio and plans to bolster marketing effort to change perception and highlight improvements.
Community and feedback
Devin encourages feedback and plans to make the process more public. For now: [email protected], jetpack.com/feedback, his Twitter @innerwebs, and devin.org are ways to reach him. He plans to use user research, one‑on‑ones with existing team members, and public engagement to inform decisions.
Measurement and the next year
With a large installed base, improvements can be measured through connection rates, review scores, successful usage of features, and user satisfaction. Devin wants to push Jetpack’s rating higher and reduce one‑star reviews tied to breakages and support gaps. He suggests checking back in 12 months to evaluate progress and invites users to test Jetpack now and report pain points and wins.
Summary
Devin’s plan for Jetpack emphasizes focus, user‑centered redesign, better onboarding, clearer product boundaries, stronger marketing, and a bold push into AI that brings .com capabilities to self‑hosted sites. The challenge is to modernize and simplify a sprawling product without alienating millions of active installations. Devin frames this as a career capstone and a team effort—one that will unfold incrementally but with big ambitions, particularly around forms and AI‑driven site building.