James LePage

Observer
DISC Type : ci

Core AI Co-Lead at WordPress

New York, New York, United States

Overview

James LePage is the Director of Engineering for AI at Automattic, where he leads the AI strategy across platforms like WordPress and WooCommerce. A graduate of Syracuse University, he is a serial founder whose most recent AI startup, WPAI, was acquired by Automattic.

Outside of his primary role, James is passionate about fostering new ventures, serving as a mentor for early-stage companies at the Blackstone LaunchPad incubator. He is also an Eagle Scout, reflecting a long-standing commitment to leadership and community.

His AI company focused on WordPress creators was acquired by Automattic, where he now leads the very division his startup aimed to serve.

Personality Overview

Curious

Assertive

Value Driven

They are generally good communicators and can be hard to convince.  They are likely to ask many questions and look heavily for supporting information. They can sound friendly and charming but can quickly change gears to become inquisitive and probing.

Topics They Care About

AI in Publishing
Leads AI engineering for WordPress, WooCommerce, and Jetpack, aiming to reimagine publishing and democratize web creation with AI tools.
Open Source AI
As a co-lead for the Core AI team at WordPress, he is focused on coordinating AI projects within the open-source ecosystem.
Entrepreneurship
A multi-time founder, having started and led companies like WPAI Inc. (acquired by Automattic), Shareclub, and Isotropic.

Media Appearances

AI is blooming in the WordPress ecosystem – James LePage, Director of Engineering, AI (Facebook video). Featured in Facebook (Cloudways)

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The future of the open web is still human – James LePage shares why writing publishing matters (Facebook post). Featured in Facebook (WordPress)

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Work History

5-2025
Core AI Co-Lead at WordPress
4-2025
Director of Engineering, AI at Automattic
12-2024 - 4-2025
Team Lead at Automattic
11-2022 - 12-2024
Founder at WPAI Inc
12-2021 - 5-2023
Co-Founder and Dir. Technology at ShareClub

Education

Bachelor of Science - BS from Syracuse University
Case Studies in Real Estate Development from NYU School of Professional Studies

More Information

Social Presence :

Prographics :

Exp : 5 Location : New York, New York, United States Job Level : Mid-senior Designation : Core AI Co-Lead at WordPress
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Insights For Selling To James

During A Call Or A Meeting

DO's

  • Use phrases like ‘clear proof that’, ‘data shows’ etc.
  • Focus on immediate action-items rather than the larger goals
  • Build rapport, it will come handy to handle hard questions later

DONT's

  • Avoid making offhand commitments
  • Don’t rely excessively on your relationship with them to win the deal
  • Don’t be too objective but make sure to pad your storytelling with data points

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with James is

  • Proven value, strong testimonials are important to them, relationships will have some weightage.
  • Will you ever get a clear answer from James

  • They are practical and friendly, don't expect a clear-cut response often.

Insights For Deal Planning

    How fast (or slow) will James move?

  • They like to be detailed and take their time to arrive at decisions.
  • Can James take some risk or not?

  • They evaluate their decisions systematically and are less likely to take risks.

You And James

Personality Compatibility


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