James Kemp

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Category: Working Notes

  • Jan 20, 2026
    No comments on It’s Not Too Late to Start Using AI as a Product Manager

    It’s Not Too Late to Start Using AI as a Product Manager

    Every few weeks, a new AI tool launches.

    Every few days, someone posts about their AI-powered workflow on X or LinkedIn.

    And if you’re anything like me, there’s this nagging feeling that you should be doing more. Using these tools better. Learning faster.

    I use Claude Desktop with AutoMem for the majority of my work as a Product Manager at WooCommerce now. I’ve got integrations with Linear for issue management, GitHub for triage context, Enterpret’s Wisdom for user feedback synthesis. I can execute faster and more effectively than I could previously, when I was manually opening dozens of browser tabs to analyse feedback patterns.

    And I still feel like there’s more I could be doing.

    If that resonates with you, good. That means you’re paying attention.

    But here’s what I want you to understand: that feeling shows you’re aware, not behind. Awareness is the first step to actually using these tools in a way that transforms how you work.

    Keep reading
  • Jan 10, 2026
    1 comment on Launch WooCommerce Playground Sites with a Single Keystroke

    Launch WooCommerce Playground Sites with a Single Keystroke

    If you’ve ever triaged bugs, you know the drill. Someone reports an issue, and your first question is: can I reproduce this on a clean install?

    For WordPress, that used to mean spinning up a site in LocalWP or WordPress Studio. Enter a title, choose your settings, wait for it to provision, then manually install WooCommerce, then install Query Monitor, then maybe a few other plugins. LocalWP has blueprints, but they’re snapshots of existing sites, so they go stale as soon as plugins release updates. And you end up with dozens of unused local installs cluttering your machine.

    Those tools are great for persistent testing sites or local development. But for quick, throwaway bug reproduction, they’re overkill.

    WordPress Playground changed this. Sites are ephemeral (not persistent, just temporary). Use it once and close the tab. No cleanup, no clutter. But the blueprint URLs are long and the JSON syntax is hard to remember.

    So I made a Raycast script that launches a fully configured WooCommerce Playground site in about two seconds. Type “Woo”, hit enter, and you’re in.

    Keep reading
  • Dec 24, 2025
    No comments on 2025: My Year in Review

    2025: My Year in Review

    Think back to how WooCommerce looked at the start of 2025. The accessibility landscape was uncertain, AI felt like a distant promise, and the idea of bringing more features into core was still taking shape. A lot has changed since then.

    This year has been one of the most rewarding of my career, both professionally and personally. I want to share the highlights: what we accomplished as a team and what happened in my life outside of work.

    Keep reading
  • Jun 23, 2025
    No comments on Making WooCommerce Accessible: How We Achieved Full Compliance

    Making WooCommerce Accessible: How We Achieved Full Compliance

    Sometimes the most important conversations start with uncomfortable truths. In early 2024, accessibility expert Amber Hinds from Equalize Digital published an audit that revealed over 50 accessibility issues on their WooCommerce website. The message was clear; our platform, powering millions of online stores, wasn’t serving everyone equally.

    Keep reading
  • Jun 3, 2025
    1 comment on How I Use AI as a Product Manager: From Chaos to Clarity

    How I Use AI as a Product Manager: From Chaos to Clarity

    Think back to how you analysed user feedback two years ago.

    For me, running Iconic (my WooCommerce plugin company which I later sold in 2021), it meant opening dozens of browser tabs: GitHub issues, Reddit threads, support tickets, forum posts. I’d spend entire afternoons copying user feedback into spreadsheets, trying to identify patterns that would shape our plugin roadmap.

    It was necessary work, but exhausting. And I always wondered: what patterns was I missing in the noise?

    Keep reading
  • May 19, 2025
    6 comments on Taking Control of My Workday with Sunsama

    Taking Control of My Workday with Sunsama

    We’ve all been there. Multiple Slack channels pinging, emails flooding in, calendar invites stacking up, and todos scattered across various tools. It’s overwhelming, and at the end of the day, I often found myself wondering what I actually accomplished.

    Two weeks ago, I started using Sunsama, and it’s changed how I approach my workday.

    Keep reading
  • Mar 21, 2024
    No comments on My First Automattic Meetup in Charlotte, NC — Plus Asheville

    My First Automattic Meetup in Charlotte, NC — Plus Asheville

    One of the hardest things about working with a remote team can be the isolation you experience from working mostly on your own. Fortunately, Automattic prevent this feeling with regular meetups and WordCamps.

    Since starting at Automattic in January, I’ve already been given the opportunity to attend my first meetup in Charlotte, NC. The product team got together for 4 days of focussed team work, and after a recommendation from my colleague, I extended my trip a few extra days in order to visit Asheville, which was a 2 hour drive away.

    Keep reading
  • Feb 22, 2024
    No comments on Building Trust with Every Interaction

    Building Trust with Every Interaction

    We’ve all been there. You’ve booked an appointment with a tradesperson and they’ve arranged to come at a certain time. Maybe you’ve booked the morning off work to wait for a package to arrive. The anticipation, the planning around it, and then the waiting. But the event never happens. The person never arrives and the package never shows.

    Keep reading

James Kemp

Helping to shape the future of ecommerce at Woo. Tech enthusiast, photographer, and advocate for seamless user experiences.

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