WP Legends Episode 92 features my conversation with Seahawk Media on my journey from co-founding GiveWP to leading Jetpack at Automattic, and what it’s like shaping a product that lives at WordPress-scale. We dig into Jetpack’s strategic focus, partnerships (including Automattic for Agencies), simplifying legacy UX, and what’s next for AI in WordPress.

I walk through my path in the WordPress ecosystem, from building GiveWP and collaborating with brands like iThemes, Kadence, LearnDash, and The Events Calendar, to taking on my new role leading Jetpack at Automattic. I talk about why I joined, how I’m thinking about simplifying Jetpack’s experience, the realities of improving a product used on millions of sites, and how Automattic’s shifts in organization and collaboration are shaping that work. I also dig into the future of AI in WordPress, what it means for content creation and block building, and why stronger product marketing and tighter feedback loops matter for where Jetpack is headed next.

I recently joined The WP Minute to talk through my transition from GiveWP to Jetpack, how GiveWP shaped how I think about product leadership, and what the next chapter of Jetpack looks like. We covered onboarding, user experience, community engagement, and why listening directly to users is such a big focus for me right now, along with how AI can level up the first run experience and deliver value faster.