Paul G.

Energizer
DISC Type : I

Chief Product Officer at Squarespace

Encinitas, California, United States

Overview

Paul is the Chief Product Officer at Squarespace, with over 25 years of experience delivering solutions for creative professionals. His career is highlighted by founding a company acquired by Macromedia and leading strategic product and design teams at Adobe. He studied Drama at Purchase College, SUNY.

His educational background in drama points to a passion for creative expression and narrative. This aligns with his professional mission to build tools that empower people to tell impactful stories, a theme consistent throughout his career in technology.

Unique fact: Paul founded, ran, and successfully sold his own company, CyberSage Software, to Macromedia in 2003.

Personality Overview

Enthusiastic

Relationship Oriented

Informal

They are not always early adopters but can be pursuaded by leveraging strong relationships.  They are really good at seeing what the long-term impacts of their decisions could be. They are friendly, approachable and love to make new connections.

Topics They Care About

Empowering Creatives
His stated passion is building tools and services that inspire and empower people to tell their best stories with impact.
Product & Design Leadership
He oversees product management and design for Squarespace, and previously led Product Management and Engineering for major business units at Adobe.
Web Design Community
He actively engages with Squarespace's community of professional web designers, highlighting events like the annual "Circle Day".

Media Appearances

Circle Day 2025: Product Keynote with Chief Product Officer Paul G. (Squarespace). Featured in Squarespace Blog

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Squarespace Appoints Paul Gubbay as Chief Product Officer. Featured in PRNewswire

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Circle Day 2025: Product Keynote with Paul Gubbay, Squarespace. Featured in YouTube

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Work History

7-2020
Chief Product Officer at Squarespace
11-2005 - 7-2020
VP, Design & Web at Adobe
3-2003 - 11-2005
Sr. Dir of Engineering at Macromedia, Inc.
1-2000 - 3-2003
President & Co-Founder at CyberSage Software
1996 - 2000
Sr. Consultant at Marotz (now acquired by Hansen)

Education

1985 - 1986
Drama from Purchase College, SUNY

More Information

Social Presence :

Prographics :

Exp : 30 Location : Encinitas, California, United States Job Level : Leadership Designation : Chief Product Officer at Squarespace
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Insights For Selling To Paul

During A Call Or A Meeting

DO's

  • Invite them for a lunch or a drink/coffee
  • Talk anecdotally about the customer experience that your product offers
  • Use adjectives like ‘amazing’, ‘coolest’, ‘unbelievable’ etc.

DONT's

  • Avoid cutting into their flow
  • Don’t be excessively objective, be a storyteller
  • 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 Paul is

  • Relationship and rapport can play an important role, sometimes more than the other factors.
  • Will you ever get a clear answer from Paul

  • They will probably never say no directly, you have to make that decision yourself.

Insights For Deal Planning

    How fast (or slow) will Paul move?

  • They are not the quickest decision makers, their friendly attitude could be misleading.
  • Can Paul take some risk or not?

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

You And Paul

Personality Compatibility


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