Michael Fountain in

Michael Fountain

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Head of Domains Search & AI Platform at Squarespace
📍 Seattle, Washington, United States

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.

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Experience
25 Years
Current Role
Head of Domains Search & AI Platform
Job Level
Mid-senior
Location
Seattle, Washington, United States
Personality Overview

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Priorities

Topics Michael cares 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.
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Career

Work history

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

Media appearances

Squarespace AI: How Does It Work and How Does It Impact Users? (Episode 12). Featured in Apple Podcasts
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Education
Bachelor of Business Administration - BBA
The University of Southern Mississippi
Completed 35 credits towards Bachelor of Music
Tennessee Technological University
Social presence
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Behavioral profile

DISC profile (public)

DISC behavioral profile

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