Jon Thornton

Energizer
DISC Type : I

Director of Engineering at Squarespace

New York, New York, United States

Overview

Jon Thornton is a Director of Engineering at Squarespace, leading the Application Platform group. With a BS from Boston University, his experience spans diverse sectors like health-tech and AI in education. He is a frequent speaker on engineering leadership and system design, and is known for his "brutal honesty and genuine competence. "

Outside of his leadership role, Jon enjoys the culture of New York City, attending rock concerts, using public transit, and visiting the citys beaches. He maintains his hands-on coding skills by contributing to a jQuery plugin in his free time, showing a sustained passion for development.

His diverse career has involved parking millions of cars, improving textbooks with AI, lowering prescription medication costs, and sending billions of emails.

Personality Overview

Big Picture Person

Believer

Informal

They are naturally enthusiastic, so take their promise with a pinch of salt.  Unlike C or D types, they are vocal with their opinions but not so much with their questions. They are not always early adopters but can be pursuaded by leveraging strong relationships.

Topics They Care About

Managing Tech Debt
He frequently speaks at conferences and on podcasts about his framework for using technical debt as a strategic tool to deliver value faster.
AI in Platforms
He has recently discussed how agentic AI is actively reshaping platform engineering at Squarespace, with a new focus on developer experience over shared code.
Engineering Leadership
He speaks about leading teams through organizational changes and business pivots, focusing on effective technical leadership for people managers.

Media Appearances

Jon has no verified media appearances

Work History

6-2025
Director of Engineering at Squarespace
8-2022 - 6-2025
Principal Engineer at Squarespace
3-2017 - 8-2022
Director Of Engineering at Squarespace
6-2016 - 1-2017
Director Of Engineering at Blink Health
9-2014 - 6-2016
Head of Consumer Technology at Knewton

Education

BS from Boston University

More Information

Social Presence :

Prographics :

Exp : 21 Location : New York, New York, United States Job Level : Mid-senior Designation : Director of Engineering at Squarespace
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Insights For Selling To Jon

During A Call Or A Meeting

DO's

  • Speak enthusiastically with energy, maintain a clear and confident tone
  • Share some stories about how you you have helped people in similar positions succeed
  • Be friendly and entertaining in your conversation

DONT's

  • Avoid overloading them with too much detail
  • Don’t assume a yes just because they have not said no
  • Avoid ifs and buts, don’t talk too much about the risks etc.

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Jon is

  • Relationship and trust can be vital with them, sometimes more than anything else.
  • Will you ever get a clear answer from Jon

  • They are unlikely to say no directly, you have to make that decision yourself.

Insights For Deal Planning

    How fast (or slow) will Jon move?

  • They are not the fastest decision makers, their friendly approach can give false positive signals.
  • Can Jon take some risk or not?

  • They can take certain risks that are unlikely to have personal consequences.

You And Jon

Personality Compatibility


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