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Greg Gottesman

Managing Director, Co-Founder, Pioneer Square Labs
Greater Seattle Area,United States
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Greg Gottesman's Overview

Total Experience70 years
CompanyPioneer Square Labs
CountryUnited States

Greg Gottesman is a highly influential figure in the Seattle tech and venture capital scene. He is a co-founder and Managing Director of Pioneer Square Labs (PSL), a startup studio and venture capital firm that creates and launches technology companies. Before PSL, Greg was a Managing Director at Madrona Venture Group for nearly two decades, where he played a crucial role in investing in and guiding numerous successful startups, including being an early investor and board member for Rover.com. He is known for his deep expertise in company creation, identifying market opportunities, and fostering entrepreneurial talent within the Pacific Northwest. Greg also has a background as an attorney and has taught entrepreneurship at the University of Washington.

Professional Summary

Greg Gottesman's work history includes a series of influential roles in various companies. Here is a detailed list of his professional journey:

Shipium - Board Observer (2025 to Present)
Pioneer Square Labs - Managing Director, Co-Founder (2015 to Present)
University of Washington - Adjunct Professor (2001 to Present)
Boundless Immigration - Board Member (2017 to Present)
SingleFile - Board Member (2024 to Present)
Joon Care - Board Member (2019 to Present)
Kevala - Board Member (2020 to Present)
Ever.green - Board Member (2021 to Present)
Gumshoe AI - Board Member (2025 to Present)
Rover.com - Co-Founder, Board Member, Founding CEO (2011 to 2024)

Notable Achievements

Co-founder and Managing Director of Pioneer Square Labs

Co-founded Pioneer Square Labs in 2015, a unique startup studio and venture fund that rapidly ideates, builds, and spins out technology companies. PSL has become a significant force in the Seattle startup ecosystem, launching numerous ventures.

Key Role at Madrona Venture Group & Early Backer of Rover.com

Served as a Managing Director at Madrona Venture Group for over 15 years (approx. 1999-2015), where he led investments in many successful companies. He was notably an early investor in and board member for Rover.com, helping it grow into a leading online marketplace for pet care.

Champion of Entrepreneurship and Company Creation

Has been instrumental in the founding and scaling of dozens of technology companies throughout his career, demonstrating a consistent ability to identify promising ideas and build strong teams around them.

Educator and Mentor in Entrepreneurship

Has contributed to the next generation of entrepreneurs by teaching courses on entrepreneurship and venture capital at the University of Washington Foster School of Business, sharing his practical insights and experience.

Educational Background

MBA, with Honors and Distinction

Harvard Business School - Year 1995

JD, with Honors; Editor, Harvard Law Review

Harvard Law School - Year 1994

Bachelor of Arts (A.B.), Phi Beta Kappa, with Honors and Distinction, Political Science and Government

Stanford University - Year 1988

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Notable news
Hiring actively
Corporate Finance
Corporate Finance
Corporate Finance
Corporate Finance
Corporate Finance

Company Overview

Pioneer Square Labs
Total employees70
HeadquartersSeattle
Founded2015

Pioneer Square Labs (PSL) is a startup studio and venture capital firm based in Seattle. PSL partners with exceptional founders to co-create and launch new technology companies from scratch, providing initial capital, strategic guidance, and hands-on operational support. They also invest in promising early-stage technology startups outside of their studio model, leveraging their expertise to help these companies grow and succeed.

Pioneer Square Labs Funding Information
$27.5M - Total Funding Raised
$15M - Most recent funding amount
2 - Number of funding rounds
Jan 27, 2020 - Latest funding round
Lead Investors:
Foundry Group
Bezos Expeditions
Madrona Venture Group
Voyager Capital
Muse Capital
Liberty Mutual Strategic Ventures

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