Devin Walker joins the Jukebox Podcast to discuss his new role as Artistic Director (head) of Jetpack at Automattic. Devin is best known as co‑founder of GiveWP and creator of WP Rollback, with extensive experience in development, design, marketing, and support. After GiveWP was acquired and time at Liquid Web, he left in August 2025 and accepted the challenge of leading Jetpack—drawn by the product’s reach and the opportunity to have broad impact within Automattic and the WordPress ecosystem.

Why Jetpack?
Devin weighed starting another independent venture against joining Automattic. Jetpack’s scale, influence, and complexity appealed to him: it touches millions of sites and integrates tightly with wordpress.com. He acknowledged Jetpack’s divisiveness and the “jack of all trades, master of none” critique, but saw room to bring focus, polish, and clearer product direction.

Scope and priorities
Jetpack bundles many capabilities—stats, backups, security, performance, social sharing, forms, VideoPress, basic SEO, and more. Devin’s immediate aim is not to keep adding disparate features but to refine and improve what exists, prioritizing the most impactful areas. Forms is a major focus: recent releases (15.2 and upcoming 15.3) include significant upgrades, and Devin leads that initiative to make forms much more useful to the majority of users while acknowledging that highly specialized power users will still need dedicated tools.

Organization and development approach
Automattic’s structure is evolving from a traditional functional org to a more matrixed model. Rather than isolated Jetpack teams, there’s now shared architecture and design resources that span .com, Jetpack, WooCommerce, and other products. This creates opportunities for tighter integration—Jetpack supplying the cloud services and “secret sauce” to enhance self‑hosted sites—while also requiring coordination across teams.

Devin describes the environment as more liquid and collaborative: engineers and designers can be focused on specific initiatives like forms, then shift to other priorities as needed. That flexibility enables better cross-product work (e.g., Jetpack + WooCommerce) but requires careful resource choices and roadmapping.

AI and the future of site building
AI is a major area of investment. Jetpack already has understated AI features—automatically generating excerpts, featured images, and other content aids—and Automattic is building a much larger AI effort to bring .com capabilities to self‑hosted WordPress via Jetpack. A sizable engineering team is working on a rewritten foundation for AI features that will act as a “content companion,” offering assistance throughout the WP admin and offering tools for visitor engagement, conversions, presales, and more.

Devin highlights Telex (Automattic’s block‑generation tool) as an example of what’s possible: AI could let users generate custom blocks or functionality on the fly (e.g., a seasonal visual effect, a bespoke block for a specific content need) and Jetpack can become the bridge that manages, deploys, and updates those generated pieces across sites.

Focus, simplification, and UX
A recurring theme is the need to simplify Jetpack’s UX and marketing. Users face confusing overlaps—multiple toggles, scattered controls, unclear dependencies with wordpress.com, and inconsistent behavior across classic and block themes. Devin wants to consolidate toggles, streamline onboarding, and apply frameworks like Jobs to Be Done to understand user goals rather than assuming feature‑driven flows.

Because Jetpack has a core install base around four million sites, changes must be careful and measured. Automattic follows a monthly release cadence, and reliability is critical: major causes of low reviews are breaking changes and poor support. Devin plans to balance careful rollouts with more aggressive improvement where safe, using onboarding and improved navigation to better explain Jetpack’s value.

Marketing and communication
Devin sees a gap in marketing resources relative to Jetpack’s potential. Historically Jetpack benefited from being an early, broad product, but the plugin ecosystem has matured and competitors now have focused marketing. He intends to boost Jetpack’s public communication—publishing more of the internal work that’s currently on P2s, refreshing messaging, and clarifying what Jetpack does and for whom. Improving public perception will be a key part of the plan alongside product changes.

Community, feedback, and next steps
Devin emphasizes using user feedback to guide changes and avoid working in a bubble. He’s been meeting across teams, documenting product histories and responsibilities, and publishing a P2 called “Connecting the Dots.” He invites users to try Jetpack as it is now, provide feedback, and follow the planned improvements.

Contact and accountability
For feedback, Devin points to [email protected], jetpack.com/feedback, or reaching him on Twitter (@innerwebs) and his site (devin.org). Nathan and Devin agreed to a public check‑in in 12 months to revisit progress and measure improvements in UX, reviews, and cohesion.

In short: Devin took on Jetpack to bring focus, polish, clearer UX, and deeper AI integration to a sprawling but powerful product. He plans to consolidate and improve core capabilities (forms, onboarding, SEO basics), integrate AI to act as a content and site-building companion, strengthen marketing and communication, and do so carefully given Jetpack’s large user base.

Devin Walker joins Automattic as Artistic Director of Jetpack — effectively head of the product — bringing a broad WordPress background: 16 years in development, design, marketing, and support; co-founder of GiveWP; creator of WP Rollback; and experience working with many WordPress brands. He took the role after weighing the risks of starting another company versus the scale and impact possible at Automattic. Jetpack’s reach and the opportunity to improve a product used by millions drew him in, despite its complexity and divisiveness in the community.

Scope and vision
– Devin’s mandate is to bring focus and clarity to Jetpack. Historically Jetpack has been “jack of all trades, master of none,” offering backups, stats, protection, performance, forms, VideoPress, SEO, and more. Many features were pioneering years ago but now face specialized competitors.
– The immediate approach is not to keep piling on new features, but to refine and polish what exists: improve user experience, strengthen core features (notably forms and SEO), consolidate overlapping UI, and prioritize what delivers the most value to the majority of users.
– Devin accepts that Jetpack won’t necessarily reach the depth of highly specialized products for the top 2% of advanced use cases, but aims for a solution that fulfills the needs of about 98% of users.

Organizational changes and product delivery
– Automattic has been shifting from a functional org (dedicated product teams) to a matrix-style setup: shared architecture and design teams working across .com, Jetpack, WooCommerce, and other products. This encourages tighter integration and reuse of common services.
– The matrix model allows engineers and designers to be shared across initiatives, enabling sprints focused on specific areas (e.g., a dedicated effort to upgrade Forms). Devin is leading the forms initiative and notes strong engineering talent at Automattic.
– This structure also supports integrating Jetpack features with other Automattic products (e.g., benefits when using WooCommerce and Jetpack together) while respecting user choice and privacy.
– Releases run on a monthly cycle; with Jetpack’s size caution is necessary — breaking changes harm many users and generate negative reviews. Devin aims to balance safety with the need to move more aggressively on improvements.

User experience and simplification
– Jetpack’s complexity creates confusion: multiple places to toggle modules, scattered settings, and inconsistent behavior between themes (classic vs block themes). Devin calls for a Jobs-to-Be-Done approach — seeing the product from user goals rather than toggles and features.
– Concrete UX goals include consolidating multiple toggle locations, simplifying onboarding and connection to WordPress.com, clarifying the product’s purpose, and reducing surprise behaviors. Devin has already seen positive results from recent onboarding improvements and wants to build on that.
– A big aim is to make Jetpack the “go-to” toolkit that takes a vanilla WordPress site to a credible, featureful state with clear, easy-to-use interfaces — the baseline solution for most users.

AI as a strategic frontier
– AI is a major and accelerating focus. Jetpack already embeds some AI features (auto-generated excerpts, featured images, content assistance) that are quietly powerful; Devin says those implementations are just the beginning.
– Automattic has large AI efforts (50+ engineers) and intends to bring many .com AI features to self-hosted WordPress via Jetpack. Upcoming plans include broader content assistance, admin tools, visitor-facing features (conversion workflows, presales Q&A, newsletter sign-up help), and deeper editor tooling.
– Telex (Automattic’s block-creation tool) illustrates the potential: prompt-driven block generation could let non-technical users create bespoke blocks on demand. Devin sees AI as the glue that binds Jetpack components and WordPress Core capabilities to enable on-the-fly, site-specific functionality.
– Current AI features will be substantially reworked as foundations evolve. Devin expects major changes in 8–12 months with deeper AI integration across the admin and site.

Marketing, perception, and community
– Devin notes Jetpack’s marketing has been quiet while the WordPress ecosystem grew louder and more specialized. Part of his job is to improve communication: clearer messaging on what Jetpack is, how it helps, and the value proposition of its free and paid tiers.
– He observes an engineering-led culture with comparatively few marketers and wants to increase marketing efforts to reshape perception and better highlight Jetpack’s capabilities and improvements.
– Transparency matters: many internal updates and P2s contain impressive work that Devin believes should be more public to change community perception.

Scale and care
– Jetpack’s active install base is large (the core at around 4 million installs), which imposes constraints: releases require caution, and changes must avoid breaking user sites. Devin wants to reduce support pain points (breaking changes and poor support are top causes of one-star reviews), improve reliability, and lift overall ratings.
– He plans to use user feedback extensively, inviting the community to report issues and share quirks, so redesigns reflect real needs rather than internal assumptions.

Next steps and engagement
– Forms upgrades are an immediate priority, with iterative improvements shipping across versions. SEO and other underdeveloped areas are also targets for enhancement or sunsetting if they don’t provide sufficient value.
– Devin is collecting internal knowledge (a “Connecting the Dots” approach) and meeting teams to map expertise across Jetpack’s varied history and features.
– He invites feedback: [email protected], jetpack.com/feedback, or via his Twitter (@innerwebs) and website (devin.org).

A public check-in
– Devin frames this as a journey and suggests checking back in 12 months to evaluate progress. The goals are clear: simplify and focus the product, ship meaningful UX and AI improvements, strengthen marketing and messaging, and raise quality and user satisfaction without breaking the enormous existing install base.

If you use Jetpack now, Devin encourages trying it and sharing what’s working, confusing, or broken — the team plans to lean on user feedback as they refine the product.

Devin Walker, recently hired by Automattic as Artistic Director (head of Jetpack), joined the Jukebox Podcast to discuss his WordPress background, why he accepted the Jetpack role, and his plans for the product. Devin co-founded GiveWP, scaled it, and later worked across notable WordPress brands. He left Liquid Web in early August 2025 and chose Automattic over starting another independent venture because of the scale, impact, and opportunity Jetpack presents.

Why Jetpack?
Devin was drawn by the challenge and the chance to work inside a company he respected. Jetpack is divisive: it offers many features (stats, backups, security, performance, forms, VideoPress, SEO, etc.) and historically has been a jack-of-all-trades that sometimes feels like a master of none. Devin sees both the opportunity and the responsibility: with focus and refinement, Jetpack can better meet the needs of the majority of users while acknowledging there will always be specialized power users who need dedicated third-party solutions.

Scope and Goals
Devin’s early priorities are to bring clarity, focus, and polish to Jetpack’s existing feature set rather than chase numerous new products. He emphasized improving areas like forms and SEO, pointing out Jetpack already does many things well (including generous free features like a CDN and VideoPress) but needs refinement, clearer product boundaries, and better UX. The aim is to make Jetpack the go‑to solution for most users—covering roughly 98% of needs—while accepting that deep niche functionality will remain the domain of specialized plugins.

Organizational Changes and Collaboration
Automattic has been shifting from functional silos to a more matrixed organization. Instead of dedicated teams for each Jetpack module, architects, engineers, and designers now collaborate across products including .com and WooCommerce. This structure aims to make products work together more cohesively. Devin is leading a forms upgrade effort (already visible in releases like 15.2 and upcoming 15.3), with a strong engineering team focused on improving core experiences.

Because Jetpack provides cloud-backed features, many advanced capabilities require OAuth/.com connections. Devin recognizes concerns about that requirement and privacy but notes the cloud infrastructure enables much of Jetpack’s “secret sauce.” The reorg also makes it easier to align Jetpack with other Automattic products and pursue shared initiatives.

AI and the Future of Jetpack
AI is a major focus. Jetpack currently includes subtle AI features—like auto-generated excerpts and featured images during publishing—but Devin describes that as “scratching the surface.” Automattic has a significant engineering effort (50+ engineers) working on AI, and Jetpack will be a primary vehicle to bring .com AI capabilities to self-hosted WordPress users. The AI roadmap includes a stronger content companion, admin-side tools, visitor-facing features (e.g., conversion and pre-sales assistance), and deeper editor integration.

Devin referenced Telex (Automattic’s block-generation tool) as an important building block. He envisions Jetpack using AI to generate blocks, customize site components, and act as a glue that ties disparate products together—making Jetpack the “supercharged” layer that enhances WordPress without constraining creativity. AI could allow users to create temporary or bespoke blocks and features by prompting, expanding what WordPress can do without requiring in-depth technical knowledge.

User Experience, Onboarding, and Marketing
A major problem Devin wants to solve is Jetpack’s confusing UX. Over time Jetpack accumulated many toggles, multiple places to enable features, and inconsistent behavior across themes and site types. This complexity leads to poor reviews—often stemming from breakage or lack of clarity—and creates friction for both novice and experienced users.

Devin plans to apply frameworks like “Jobs to Be Done” to understand user goals and simplify onboarding and navigation. Recent changes to the connection onboarding improved successful connections, and Devin wants to expand that approach, consolidating toggles and modules and making feature discovery and configuration clearer. He stresses the importance of user feedback and intends to engage the community as changes roll out.

Marketing has lagged relative to the broader marketplace. Jetpack historically benefited from being an early, built-in champion for many features, but the WordPress ecosystem has matured with many focused competitors and stronger marketing. Devin plans to increase marketing efforts, publish more of Automattic’s internal work (P2 content), clarify Jetpack’s messaging, and refresh the website to better explain what Jetpack is and who it serves.

Shipping Carefully at Scale
Jetpack’s active install base—around 4 million core installs—means changes must be cautious. There’s tension between moving quickly to improve product and avoiding breaking a large number of sites. Automattic currently ships monthly releases and tries to balance careful rollout with needed improvements. Devin wants to be more aggressive where safe, but acknowledges the need to raise satisfaction (e.g., moving the ratings above 4.0) without causing regressions.

How to Give Feedback
Devin invited feedback from users: [email protected], jetpack.com/feedback, Twitter @innerwebs, or devin.org. He plans to make feedback channels and progress more public and wants community input to prioritize and validate changes.

Next Steps and Check-ins
Devin’s immediate work includes continuing the forms overhaul, refining onboarding, improving UI consistency, advancing AI features, and ramping up marketing. He suggested a follow-up check-in in 12 months to evaluate progress, metrics like user reviews and onboarding success, and the visible improvements to Jetpack’s UX and AI capabilities.

Conclusion
Devin Walker accepts the challenge of steering Jetpack toward a more focused, polished, and integrated future. His priorities are simplifying UX, improving core features (notably forms and AI-driven capabilities), aligning teams across Automattic, and raising marketing and communications. Given Jetpack’s scale and complexity, the work will be incremental and cautious but aims to deliver clearer value to most WordPress users.