Hello Awesome Motive

What I’ve been up to

WordPress.com is where I have gained most of my recent plugin development experience. As a Code Wrangler (read Senior Software Engineer) on one of Automattic’s payment teams, I worked on plugin functionality for a billing system which served millions of users and ran more than 150k subscription actions each day.

Some of the projects I owned included refactoring legacy codebases to use modern Stripe APIs for users preferring local payment methods, ensuring automated renewal compliance by introducing e-mandates for credit card transactions, updating email receipts for compliance with tax requirements of 23 different countries, and improving internal tools for the teams that supported our WordPress.com, Jetpack, and Akismet customers with their billing questions.

Before joining Automattic, I worked with companies to build custom operational solutions for their business needs, such as a CRM and sales quoting tool, or a summer camp application tied to WooCommerce.

Professional Summary

  • Life-long student, proactive communicator, and technical alchemist
  • Expert at managing projects with stakeholders across multiple teams and disciplines
  • 3 years of payment engineering contributions impacting over $1.5 million in annual revenue
  • 10 years of experience in both backend and frontend WordPress development

Let’s talk about The Loop

My favorite thing to explain about WordPress is the concept of The Loop. Not technically a single function or hook, but it definitely uses them.

<?php 
if (have_posts()) {
 while (have_posts()) {
     the_post(); 
     // Do
     // something
     // awesome
 } // end while
} // end if
?>

When a newcomer understands how The Loop works, that is the beginning of really understanding WordPress. One of the many super powers of WordPress is the ability to iterate over multiple datasets to display, or interact with, the data in a meaningful way.

Everything else about WordPress, from displaying custom post types to building engaging archive pages to organizing data with taxonomies, builds off the idea that content can be displayed uniformly.

When I meet people who are dipping their toes in the water of WordPress development, I always point them to The Loop page in the Codex. All other concepts, even template hierarchy, are easier to understand when a developer has the foundation of looping through datasets.

A Jess-of-all-trades

I have grown into being a multi-disciplined developer by being a problem oriented learner. When presented with a problem, I investigate, propose a solution, seek feedback, and then learn whatever skills and stack I need to execute. In the close to 20 years I have been using WordPress, and the ten years I have specifically been working in development, expanding my knowledge base by solving problems has served me, and the stakeholders I work with, really well. I am not the type of nerd who remembers PHP’s birthday or knows the names of the parents of code. I am the type of nerd who gets excited about hacking ACF to save data to custom tables to reduce bloat (once reduced 300K+ rows of postmeta to less than 50k rows of a custom table). I am also a future thinker who always considers what maintaining the code, or releasing the next feature, will look like.

Skills

  • Technical Documentation
  • Project Management
  • PHP, TypeScript, React, JavaScript, jQuery, HTML, CSS
  • Git Version Control
  • Third-Party API Integrations (Stripe)

Beyond the code, I am an active journaler who brings the skill of self-documentation with me to work. It is a personal goal to document every step of a project, including the investigation and thought process behind my approach, not just the end result. Every project I own should be able to be picked up without more than a few question marks.

Need a team mom lead?

While I don’t usually carry a lead title, I take care of my teams and the people I work with. Sometimes that is by helping to organize meetups, initiating team rituals such as annual retrospectives, or just keeping an eye on my people for signs of burn out. I am a servant leader who brings people together and helps them bond.

Even working remotely, as I have for the last 10 years, there are so many ways to make people feel seen and valued. A funny GIF, a quick checkin, or a handwritten thank you sent via snail mail are all ways to stay connected while working separately.

Jess is simply an amazing team member. She really helped our team to bond.

Eleanor Martin
Senior Software Engineer
Automattic

[Jess is] a natural leader [who] put together activities that were a joy to participate in.

David Rothstein
Senior Software Engineer
Automattic

I have very much enjoyed working with Jess and I’m envious of her next team

Payton Swick
Senior Software Engineer
Automattic

Recent Projects

Open Source Contributor – Calypso | December 2024 – June 2025 | Merged to Production

Summary: Create a better subscription management experience for WordPress.com users, including adding the ability to sort, filter, and search active subscriptions.

GitHub Issue #86616

Related PRs:

Custom Boilerplate Plugin | June 2025 | Work in Progress

Summary: Add a custom user role (including meta fields and taxonomies) and use the DataViews component to display the custom users. See “Making a SCUD plugin”.

GitHub Repository: JessBoctor/simple-custom-user-display

Related PRs: