A New Chapter: Joining Automattic to Lead Jetpack

A few months ago, I shared that I was closing a major chapter of my career. I had stepped away from Give and Stellar, teams and products that meant the world to me. Leaving something you helped build from the ground up is never easy. But I knew it was time for a new challenge and a new way to make an impact in the WordPress ecosystem.

Since then, I’ve had countless conversations with friends, founders, and peers across WordPress. I explored investment opportunities, brainstormed new product ideas, and seriously considered building something from scratch again. At the same time, I gave myself permission to slow down. To create for the joy of it. To write, code, and reset.

I also wanted to give back to the community that shaped my career. That’s what led me to restart the San Diego WordPress Meetup, creating a local space for people to learn, connect, and share their WordPress journeys.

Around this time, I reconnected with Matt Mullenweg, co-founder of WordPress and CEO of Automattic. We had previously worked together on a project for a nonprofit he’s deeply passionate about, which gave him a chance to see my work at Give firsthand.

He appreciated my holistic approach to building products — blending design, development, marketing, and customer success. Those conversations naturally evolved into a broader discussion about Jetpack and Automattic’s vision for the future. The more we talked, the clearer it became that this was an opportunity where I could make a real impact.

The role? Guiding Jetpack into its next era as its Artistic Director (or if you prefer, Head of Jetpack).

Finding the Next Challenge

As my semi-sabbatical went on, I realized my next step would take one of two paths.

Path one: start a new company from scratch, build a product, find partners, raise capital, and try to recreate the magic again. That road is thrilling but uncertain. After a decade of startups, I wanted to focus on something with broader, lasting impact.

Path two: join a company whose products and mission I deeply believe in, where I could use my experience to help shape and elevate what already exists. Automattic and Jetpack in particular fit that vision perfectly.

Jetpack is one of the most powerful and far-reaching products in the WordPress ecosystem. It connects millions of self-hosted sites to the same infrastructure and services that power WordPress.com, from backups, performance optimization, and security to stats, AI tools, and publishing enhancements. It’s essentially a bridge between the best of open-source WordPress and Automattic’s cloud services.

Yet despite its reach and utility, Jetpack has long been misunderstood. Many users see it as a monolith, unclear on what it actually offers or why they should use it. The product’s depth and value are immense, but its identity has become fragmented over time.

That’s exactly the kind of challenge I love, and it’s one worth solving. Jetpack deserves to have its story told clearly, to be seen for the innovation it brings and the problems it quietly solves for millions of users. Helping refocus that narrative is one of my main goals.

When the opportunity came to lead Jetpack’s next phase, to reimagine its brand, unify its experience, and help it reach its full potential, it felt like the right move. This role lets me bring together everything I’ve learned about product, design, marketing, and community. It’s the right challenge at the right time.

Automattic and the Road Ahead

Automattic has been quietly evolving. It’s been building stronger teams, empowering product leaders, and doubling down on customer impact. Joining now means stepping into that momentum at a pivotal time.

…and there’s already a lot of momentum, and a great team:

What excites me most is Automattic’s renewed focus on the jobs our customers need done. Helping site owners, creators, and developers accomplish their goals more simply and powerfully. That’s the same mindset that’s driven my entire career, and I can’t wait to help bring it to life at scale.

Looking Forward

I’m under no illusion about the road ahead. Jetpack’s reputation in the community is complex; some love it, some don’t. But I see that as an opportunity. My priority is listening to our users, to the community, and to our partners. The best products are built from understanding, not assumptions.

Last week was my first official week at Automattic. Like every new hire, I spent time doing a support rotation, learning firsthand about our users’ challenges and successes. It’s been eye-opening. I’ve already learned a ton, and I’m just getting started.

Over the next year, you’ll start to see meaningful changes in how Jetpack looks, feels, and communicates its value. It’s going to take time and a lot of collaboration, but I’m confident we can build something remarkable. Something that reflects the very best of what WordPress can be.

In Closing

I couldn’t be more excited to start this new chapter with Automattic, with Jetpack, and with all of you in the WordPress community who continue to inspire me daily.

Here’s to the next era. 🚀