One Year at Automattic: The Ups, the Downs, and What’s Next for Jetpack
Wow, I can’t believe it’s already been a year at Automattic. It’s been a fun and exciting journey, and I want to take a moment to reflect on my time leading Jetpack.
Before writing this, I looked back at the post where I announced my move to Automattic. In it, I wrote that over the next year you’d start to see meaningful changes in how Jetpack looks, feels, and communicates its value.
On how it looks, the good news is it’s gotten a lot better. On how it feels, the answer is… we’re getting there. And on communicating its real value, we’re just getting started again.
It was also a year of ups and downs, for Jetpack, for Automattic, and for me. Here’s my honest look back.
Joining Mid-Reorg
I arrived in the middle of a pretty significant reorganization. Automattic was moving to a more matrixed structure, and the people working on Jetpack were spread across about a dozen teams (all code-named), most of them inside a larger Architecture org. There was no dedicated Jetpack marketing team, and no one on the development side was accountable for Jetpack as a whole.
Honestly, it felt like herding cats. Teams would get direction from me, the new person in a new product org, while also getting direction from other parts of the org. Priorities shifted without my knowing. Projects started and stopped. Each team worked its own way. Some used Linear, some didn’t, and every P2 looked different. At times it felt rudderless.
It felt more like advocating than leading.
A few people encouraged me to step in and “fill the void” myself, and while I appreciated the advice, it wasn’t one I thought would be a good solution for the company and for the product I’m responsible for.
One person can’t be the product lead, project manager, and marketer at once and do any of them well, no matter how good you are with AI. So, I was a bit of a squeaky wheel about the issues I was seeing and how it was hindering Jetpack (and other products).
Despite this, we got good things done. Jetpack’s UI unification is the project I’m proudest of. Our designers and engineers brought in shared design elements, a unified header and footer, and a consistent frame to Jetpack’s admin. Much of Jetpack now feels like modern WordPress. Before, it was a bit of a mess.
We also rebuilt jetpack.com from the ground up. It launched in August, and it’s already much easier to build on and improve.
Building With What We Had
As I settled in, I decided to make the best of the org structure we had and ship as much as possible, even without a focused team. Build with what we had, essentially.
In March, Jetpack Social got a major upgrade with per-network customization, unified previews, and share history.
In April, Automattic ran Radical Speed Month, a company-wide push where hundreds of two-person teams built and shipped in the open. A small group shipped most of the Jetpack UI modernization list in a month, and the jetpack.com rebuild started there too. It was also the first hint of the “duos” model.
We also got closer to the people using Jetpack. I talked with customers, from longtime WordPress pros to an agency managing hundreds of sites. Matt joined our product review calls, and our VideoPress session with him led to rebuilding the admin UI and player from scratch. In June, I spent time with the community at WordCamp Europe in Krakow and with colleagues at a product meetup in Porto.
After the travel, we continued to progress with Jetpack, albeit slower and less focused than I’d like. And not everything went smoothly. In July, Jetpack 16.0 shipped with a bug that left some dashboards blank, and we followed up with a quick fix. This stuff happens sometimes, and the good news is we learned from it.
A Second Reorg, and Moving Too Fast
In late July, there was a mini reorg for Jetpack. The change moved a number of developers out of their Architecture teams and into two-person duos working on Jetpack and reporting to me.
Many of these developers had a real affinity for their teams. They’d worked closely together for more than a year, and many had been to one or more meetups together. Having that world change overnight, on top of everything else going on, was not lost on me.
My mistake was not recognizing it early enough. I tried to put too much structure in place, too quickly, on a brand-new team.
Within the first week, the team pushed back with good questions. What happens to the ongoing work that doesn’t fit neatly into a project? Who owns what? Is the framework itself open to change? We tried to communicate ahead of time, but clearly it wasn’t enough. That was an oversight on my end.
So we simplified. For the first cycle, we asked for three things: one project per duo, a weekly update, and a short note on what shipped. Everything else could wait. Now we’re shaping how we work in phases, together with the team.
I like to move fast, and I’ve said before that I need to slow my roll. This was a good reminder why.
Steph Anderson has been pivotal to getting this right. She joined in June as Jetpack’s Program Manager and has been a solid addition to the team. She makes sure everyone is on the same page and holds the entire workflow together.
Our First Cycle
We just wrapped our first cycle together: three weeks of building, then a week of cooldown. Most of what we bet on shipped. A couple of highlights:
- Jetpack 16.3 renamed “Products” to “Features” in My Jetpack. Turn a feature off and it actually leaves your sidebar. We also stopped upselling things you already pay for.
- Jetpack Boost 4.8 puts your speed score, score history, and the “Run speed test” button on one dashboard.
Then we held our first retro. The three-weeks-on, one-week-off rhythm worked. So did having a built-in reviewer in your duo partner, and the freedom to pitch your own projects. What didn’t work: some bets were too big, scope settled after building had started, and unplanned work kept showing up. One of the bets that ran over was mine. It was too big going in, and I should have cut it sooner.
It’s one cycle. This team is still new and untested, and I don’t want to oversell it. But the early signs are good.
In-person time matters, especially for a group that just lost the teams it knew. We’re starting with a small meetup pilot, and I’m working on getting all of the duos together next year.
September at Automattic
It’s hard to write about this year without mentioning what’s been happening at Automattic.
The WP Engine lawsuit has been running in the background my entire first year. Then in September, Automattic’s board tried to remove Matt as CEO. Two days later, he was back.
That one was rattling. Matt brought me in personally, and many of my colleagues have long relationships with him and deep respect for what he’s built.
So I dealt with it the way I know best. I stayed focused on what I could control, the team and the work, while waiting to see how it played out before deciding anything. I also opened up “office hours” so anyone could come talk about it, decompress, or talk about something else entirely.
Matt has his faults, like all of us. But he’s been steady in his commitment to open source, WordPress, and our mission. That’s why I’m here at Automattic. I share the same commitment.
An Automattic without Matt wouldn’t be a place I could see myself working, and it would be deeply concerning for open source and WordPress.
Jetpack Is Back on a Better Trajectory
There are real challenges ahead. Still, things are moving in the right direction again.
Jetpack AI is a real growth category, up about 12x this year. Credit goes to the team building it. Our part has been helping guide and position it. See jetpack.com/ai.
The new jetpack.com is performing well, and we’re restarting marketing. Stephen Edde joined as our Senior Product Marketing Manager, and marketing is back in motion.
We also have two strong designers in Adam Pickering and Eder Rengifo, though it’s hard to call them just designers. They both have serious development chops and build real product. Add a strong core group of engineers, and Jetpack finally has a dedicated team behind it.
What’s Next for Jetpack
The goal for the year ahead is a simpler Jetpack:
- Modular features. Use what you need. Turn off what you don’t, and it gets out of the way.
- Smart onboarding and feature introductions, so new users see what matters to them first instead of everything at once.
- Clearer pricing that’s easier to understand.
- AI as the foundation. Jetpack should work with the AI tools you already use, and act as the smart glue across Jetpack’s products and WordPress core.
What am I looking forward to most? Seeing what this team can do over a full year, not just one cycle. Getting everyone together in person. And ship baby, ship. 🛳️
Year one didn’t go exactly how I pictured it. Two reorgs, a few mistakes of my own, and a wild September. But Jetpack is in a better place than it was a year ago, and it feels like we’re just getting started.
Thanks to everyone who’s helped along the way. Cheers to year two. 🚀