Two Months In, Why I’m Optimistic About Jetpack’s Future

My first two months at Automattic have been a mix of learning, observing, and starting to shape where Jetpack goes next. It has been energizing, challenging, and eye-opening in all the right ways. I came in ready to help define Jetpack’s future, and these early weeks have given me a clearer view of the opportunities ahead.

Automattic is layered. The async culture, the globally distributed team, the decision-making style, and the depth of product history all create a learning curve that rewards patience. Of which, admittedly, I have little at times. I like to hit the ground running, but I’ve learned I need to slow my roll… at least a bit.

So I’ve spent time reading gobs of P2s, asking countless questions, following conversations, having many 1:1s, and letting the context build. Week by week, the picture sharpens. I’ve spent most of my career working either fully or mostly remote, so much of this wasn’t new, but at this scale, I found I had, and still do have, plenty to learn.

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Early Observations That Shaped My First Two Months

It’s been a while since I’ve been at a new company. Automattic makes you feel special when you join. Check how super stoked I was to visit the A8C NYC office:

That said, here are some early observations that shaped how I approached the deeper lessons that followed. They set the stage for understanding where Jetpack fits inside the broader ecosystem and where its biggest opportunities lie.

Finding Jetpack’s north star

One of the most important questions ahead is whether Jetpack should optimize for ecosystem impact or revenue, or find the right balance between the two. The tension is natural. Jetpack has a wide reach and deep capabilities, but a product of this scale needs a clear purpose that guides decisions.

Automattic’s creed clearly states:

I am more motivated by impact than money

Automattic’s Creed

While that’s so true, I come from a bootstrapped success story. We talked about impact and money in the same sentence. Revenue, cash, money… whatever you want to call it, simply put: makes the wheels turn. So there needs to be a balance.

Alignment across a massive product portfolio is complex

Automattic has a broad and impressive product portfolio, from WordPress.com to WooCommerce to Tumblr, Beeper, Day One and beyond:

Each carries its own roadmap and long standing history. Jetpack sits at the intersection of many of these efforts, which creates opportunity but also complexity.

Understanding how these products relate, where they intersect, and where they diverge has been essential.

Marketing resources are tight, yet talented, and supporting Jetpack matters

Jetpack’s next phase will require strong storytelling, more precise positioning, and more consistent communication. Marketing already supports a wide range of Automattic products, which means their attention is naturally spread across many priorities.

As Jetpack evolves, having more focused marketing support will help us articulate its value and momentum in a way that resonates with the broader community.

The WordPress community is open to Jetpack’s next chapter

The UI and UX previews I’ve shared on X and LinkedIn generated far more excitement than I expected. Builders, designers, and longtime users reshared and commented with real enthusiasm.

Curious what you think of this new @jetpack form submissions UI. Feels a lot smoother to review entries now.#WordPress pic.twitter.com/ZxTxwUHiVn

— Devin Walker (@innerwebs) November 18, 2025

This told me something important. People want Jetpack to evolve. They want simplicity, clarity, and a product that feels modern again.

That enthusiasm is real, and we should springboard off it.

Indecision, boldness, and startup energy

Automattic values thoughtful discussion, but there are moments where speed matters. I’ve been surprised by how sometimes small decisions expand into long P2 threads and cross-team discussions.

One example stood out early. A simple adjustment in Jetpack sparked more discussion time than the change itself warranted. It was a useful reminder that decision velocity is a competitive advantage.

These aren’t problems, they’re opportunities to tighten how we operate.

“The speed of success is determined by the speed of decision-making. Every delayed decision is an opportunity lost, while decisive action creates momentum that carries a business forward.” – Allison Dunn

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The Lessons So Far

These lessons emerged as I dug deeper into how Jetpack works, how Automattic organizes around shared resources, and how decisions move through the company.

The functional org is powerful, but it demands clarity

Automattic’s functional structure means no traditional, siloed product teams. Instead, you draw from shared engineering, design, marketing, and support groups. When alignment is strong, this unlocks flexibility and speed. When it isn’t, momentum slows.

Understanding who to pull in at the right moment has been an important part of the ramp up. Automattic also has a lot of internal code names for teams, which have been somewhat difficult for me to navigate. I created a glossary of Jetpack experts and teams on the Jetpack P2, which I now own.

Jetpack’s surface area is bigger than expected

Jetpack touches a lot at Automattic. Stats, backups, newsletters, AI tools, media handling, security, the connection layer, WP.com infra, and partner integrations.

Small changes can ripple far. This doesn’t slow us down, it just means we need context before we move. As well, ownership of Jetpack’s submodules, from Stats to AI to Content, means I have to navigate and weave through multiple additional layers to get work done. Much of this I’m still learning.

Alignment is often the real work

Ideas are easy. Alignment is the hard part. In a functional org, alignment is relational more than hierarchical. That’s where my many 1-on-1s have helped. It’s essential to build a relationship first. Next, it’s built through conversations, context, trust, and clarity.

People genuinely care

The passion across the company has been energizing. One of the reason’s I joined Automattic was to work with the best in WordPress.

Code Wranglers (developers), designers, Happiness Engineers (support/customer success), PMs, leadership, and everyone in-between all share an authentic desire to make Automattic, Jetpack, and WordPress better.

It’s impossible not to feel motivated by that energy.

Common Misconceptions About Jetpack (From the Outside Looking In)

After fifteen years in the WordPress community, and now two months behind the scenes seeing how Jetpack is actually built, maintained, and operated, I can confidently say that many long-standing misconceptions never had or no longer reflect the reality of the product.

These aren’t criticisms from the community, they’re simply outdated assumptions that haven’t kept up with how much Jetpack has evolved.

A few that still circulate:

• “Jetpack slows down your site.” In practice, Jetpack loads features conditionally, and tools like the image CDN and Boost improve performance on most sites. Now, if you go hog wild or have a shaky host, things can go askew, as with any WP plugin.
• “Jetpack is bloated.” Jetpack is modular. Only the features you enable actually run. The rest stays dormant. I’ve pulled down the monorepo, looked into this, and tested.
• “Jetpack forces you into WordPress.com.” The connection flow simply unlocks cloud powered services. Jetpack works on every host. XML-RPC is required, but that’s a topic for another day.
• “Jetpack collects data for Automattic.” Internally, I’ve looked into this. Data is used only to operate the services you’ve turned on and to provide better support. We don’t creep on you or your data for nefarious reasons, and of course, never sell it.
• “Jetpack hasn’t evolved in years.” A lot of progress has happened quietly behind the scenes, even if the messaging hasn’t always showcased it.

All the reasons above are why I’m working to rev the marketing engine back up, starting with my personal one-man campaign on social:

Seeing Jetpack from the inside has reinforced how much value it provides and how much room there is to reshape its story.

Thinking Bigger About Jetpack

As I’ve learned more, my belief in Jetpack’s potential has only grown. I no longer see it as just a plugin. I see it as the services layer for the entire WordPress ecosystem.

AI workflows, media handling, backups, performance, newsletters, search, site connections, and cross site deployment.

Jetpack already does many of these, but not yet in a unified, intentional way. That’s the opportunity. AI specifically can unlock so much more.

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How Jetpack Can Help Deliver AI to Self Hosted WordPress

Automattic is moving quickly with AI. Tools like Telex already let creators build blocks and layouts through natural language, but the workflow has limitations.

Jetpack can change that.

Right now:

• Telex doesn’t know your site’s context.
• Dynamic blocks often require manual finishing.
• Each generated block becomes a separate plugin you must install manually.

Jetpack is already the connection layer between self hosted sites and Automattic’s cloud. It can become the vessel that delivers AI powered workflows directly into the WordPress experience.

Imagine this:

You generate a block in Telex. Instead of downloading anything, Jetpack deploys it directly to your site or network. Updates sync automatically. The block understands the environment it lives in. Everything feels seamless.

That’s the kind of future we can unlock.

Here’s a quick five-minute flowchart to show the concept. It’s rough, but it gets the point across:

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What’s Next

The next few months will be about sharpening Jetpack’s purpose, improving alignment, and identifying the highest impact areas to invest in. Clear direction and decisive execution will matter more than ever.

I’m still learning how Automattic operates, how decisions flow, and how teams collaborate across such a broad and distributed company. But the more I learn, the more optimistic I become.

Jetpack has the foundation, reach, community goodwill, and opportunity to become something much bigger.

Two months in, I’m more energized than ever. Jetpack’s next chapter hasn’t been written yet, and I’m grateful to help shape it.