Michael Fountain

Commander
DISC Type : D

Head of Domains Search & AI Platform at Squarespace

Seattle, Washington, United States

Overview

Michael is an entrepreneurial product leader at Squarespace, heading the Domains Search & AI Platform. With a background in engineering and a BBA from The University of Southern Mississippi, he specializes in launching innovative 0-to-1 solutions and has founded two startups. Colleagues describe him as technically sharp, strategically astute, and creative.

Beyond his professional focus on AI and product development, Michael has a background in music, having completed significant coursework towards a Bachelor of Music at Tennessee Technological University. He is passionate about empowering other entrepreneurs to succeed and build their businesses online.

Unique Fact: Michael received a “Just Do It” award directly from Jeff Bezos for his innovative work on a project-tracking tool.

Personality Overview

Impact-Driven

Very Quick

Risk-Taker

They are less concerned about the product and more about its potential impact.  They do not care very much about building rapport or relationships. They put a lot of effort into ensuring personal success.

Topics They Care About

Intelligent Search
He is leading the creation of a new AI-driven search platform at Squarespace, focusing on user intent rather than just keyword matching to help entrepreneurs.
AI in Product
He believes AI lowers the execution barrier for product management, emphasizing the growing importance of empathy, strategic intuition, and foundational product skills.
Empowering Entrepreneurs
A core theme in his career, from creating software that enabled 15k entrepreneurs to his current work helping people find the perfect domain for their dream.

Media Appearances

Squarespace AI: How Does It Work and How Does It Impact Users? (Episode 12). Featured in Apple Podcasts

See Now

Work History

11-2025
Head of Domains Search & AI Platform at Squarespace
3-2024 - 11-2025
Head of Enterprise AI Search & Integrations Platform at MasterControl
5-2023 - 3-2024
Senior Manager of Product Management, Enterprise AI Search at DocuSign
5-2022 - 5-2023
Guest Speaker at Leading the Product
7-2021 - 5-2023
Lead Product Manager, Search Platform at DocuSign

Education

Bachelor of Business Administration - BBA from The University of Southern Mississippi
Completed 35 credits towards Bachelor of Music from Tennessee Technological University

More Information

Social Presence :

Prographics :

Exp : 25 Location : Seattle, Washington, United States Job Level : Mid-senior Designation : Head of Domains Search & AI Platform at Squarespace
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Insights For Selling To Michael

During A Call Or A Meeting

DO's

  • Help them weigh the risks by sharing objective proof points without becoming too analytical
  • When negotiating terms, help them build an impression that they are the ones calling the shots
  • Use phrases like ‘it’s your decision’, ‘strategic impact’ etc.

DONT's

  • Do not back off when challenged, respond with a confident, objective answer instead
  • Don’t take too much time in sending them information if they ask for any
  • Don't try too hard to forge relationships with them

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Michael is

  • Confidence in impact is paramount to them, followed by a sense of achievement and ROI.
  • Will you ever get a clear answer from Michael

  • If they decide not to go ahead, they will say no without hesitation.

Insights For Deal Planning

    How fast (or slow) will Michael move?

  • If convinced, they can reach decisions quite fast.
  • Can Michael take some risk or not?

  • They do not shy away from taking risks, but can be quite binary about them.

You And Michael

Personality Compatibility


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