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Greg Gottesman, Co-Founder & Managing Director at Pioneer Square Labs

Greg Gottesman

Co-Founder & Managing Director @ Pioneer Square Labs

Seattle, United States

Greg Gottesman is a Managing Director and Co-Founder of PSL. Prior to PSL, Greg served as one of the three initial Managing Directors of Madrona Venture Group, where he worked for almost 20 years. He also co-founded and led Madrona Venture Labs. Greg represents PSL on the boards of Boundless, Cash, LumaTax, and NextStep. He is also the founder,current board member, and former CEO of Rover.com. “Venture is about finding truly great entrepreneurs and supporting their efforts in every way possible. The rest is noise.”

Total investments:
15
Last investment:
Lead investor:
20%

Last updated:

Industries Greg Gottesman invests in

NewsSoftwareAnalyticsMarketplacePet

Stages Greg Gottesman invests in

Series CFunding RoundSeries ASeries BSeed

Countries Greg Gottesman invests in

United States

Contacts

TypeContactValidation
Work email
Personal email
Work phone
Personal phone
Socials

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Investment Focus

Industry

  • News 2 (13%)
  • Software 2 (13%)
  • Analytics 2 (13%)
  • Marketplace 2 (13%)
  • Pet 1 (7%)
See all 24 industries →

Stage

  • Series C 3 (20%)
  • Funding Round 3 (20%)
  • Series A 2 (13%)
  • Series B 2 (13%)
  • Seed 1 (7%)
See all 8 stages →

Investments

CompanyDescriptionRoundLinks
Tin Can Tin Can
Far Homes makes to find, buy and manage homes abroad. $3.5M / Seed / Sep 15, 2025
Rover Rover
Rover.com connects pet parents with the nation’s largest network of loving and trustworthy pet sitters and dog walkers. Through Rover, pet parents can discover, book, and manage personalized care for their dogs, including pet sitting, dog walking, in-home dog boarding, and doggy daycare. Founded on the belief that everyone should have theopportunity to experience the unconditional love of a dog, Rover improves and simplifies life for pet parents and the dogs they love. $65M / Series F / Jul 20, 2017
Rover Rover
Rover.com connects pet parents with the nation’s largest network of loving and trustworthy pet sitters and dog walkers. Through Rover, pet parents can discover, book, and manage personalized care for their dogs, including pet sitting, dog walking, in-home dog boarding, and doggy daycare. Founded on the belief that everyone should have theopportunity to experience the unconditional love of a dog, Rover improves and simplifies life for pet parents and the dogs they love. $40M / Series E / Sep 09, 2016
Amperity Amperity
Amperity’s mission is to help people use data to serve the customer. They are revolutionizing the way companies connect, identify, and understand their customers by leveraging artificial intelligence to deliver a truly comprehensive and actionable Customer 360. This view improves marketing performance, fuels accurate customer insights, and enablesworld-class customer experiences. With Amperity, technical teams are freed from endless integration and data management, and business teams have direct access to the comprehensive data they need to build long-term customer loyalty and drive growth. Amperity serves many of the world’s most loved brands, including Alaska Airlines, Starbucks, The Gap Inc, Moët Hennessy USA, Wynn Resorts, Kendra Scott, Lucky Brand, Planet Fitness, Seattle Sounders, Stanley, and many more. $9M / Series A / Feb 05, 2016
Rover Rover
Rover.com connects pet parents with the nation’s largest network of loving and trustworthy pet sitters and dog walkers. Through Rover, pet parents can discover, book, and manage personalized care for their dogs, including pet sitting, dog walking, in-home dog boarding, and doggy daycare. Founded on the belief that everyone should have theopportunity to experience the unconditional love of a dog, Rover improves and simplifies life for pet parents and the dogs they love. $25M / Series D / Mar 19, 2015
Jobalign Jobalign
Jobalign.com is the leading mobile and bilingual cloud based recruiting technology and marketplace for hourly jobs.Jobalign was founded to make the process of hiring hourly workers simple and efficient by reinventing in the cloud a series of dated and inefficient systems and processes used to match over 44 million low-wage workers with jobsevery year. It makes it easy to find, apply and get matched for jobs from any mobile phone, tablet or computer. Employers pay only for local pre-screened candidates or per-hire. The company serves directly and through their network of certified partners, mid-size and very large corporations that, on average, report a reduction of 60 percent in recruitment expenses and 50 percent in time-to-hire, while saving hundreds of hours in manual pre-screening. For job seekers, the experience is mobile, and free of advertising and marketing solicitations -- ultimately reducing their time to get hired. Jobalign is a private company headquartered in Kirkland, Wash. $7M / Series B / May 28, 2014
Rover Rover
Rover.com connects pet parents with the nation’s largest network of loving and trustworthy pet sitters and dog walkers. Through Rover, pet parents can discover, book, and manage personalized care for their dogs, including pet sitting, dog walking, in-home dog boarding, and doggy daycare. Founded on the belief that everyone should have theopportunity to experience the unconditional love of a dog, Rover improves and simplifies life for pet parents and the dogs they love. $12M / Series C / Mar 12, 2014
Jobalign Jobalign
Jobalign.com is the leading mobile and bilingual cloud based recruiting technology and marketplace for hourly jobs.Jobalign was founded to make the process of hiring hourly workers simple and efficient by reinventing in the cloud a series of dated and inefficient systems and processes used to match over 44 million low-wage workers with jobsevery year. It makes it easy to find, apply and get matched for jobs from any mobile phone, tablet or computer. Employers pay only for local pre-screened candidates or per-hire. The company serves directly and through their network of certified partners, mid-size and very large corporations that, on average, report a reduction of 60 percent in recruitment expenses and 50 percent in time-to-hire, while saving hundreds of hours in manual pre-screening. For job seekers, the experience is mobile, and free of advertising and marketing solicitations -- ultimately reducing their time to get hired. Jobalign is a private company headquartered in Kirkland, Wash. $4.3M / Series A / Oct 08, 2013
Rover Rover
Rover.com connects pet parents with the nation’s largest network of loving and trustworthy pet sitters and dog walkers. Through Rover, pet parents can discover, book, and manage personalized care for their dogs, including pet sitting, dog walking, in-home dog boarding, and doggy daycare. Founded on the belief that everyone should have theopportunity to experience the unconditional love of a dog, Rover improves and simplifies life for pet parents and the dogs they love. $3.5M / Series B / Jul 30, 2013
Decide Decide
Backed by early investors in Amazon, Google and eBay, Decide is a team of Seattle data scientists committed to helping consumers easily find the highest rated products and the best times to buy based on billions of data points from across the Web. Decide's price predictions have been 80 percent accurate and have helped uncover $200 million insavings. The company was co-founded by Internet search pioneer Prof. Oren Etzioni, founder of Farecast, the travel price predictor, and Netbot, the web's first comparison-shopping engine. The Seattle-based company has raised $17M in venture capital from Paul Allen's Vulcan Capital, Maveron and Madrona Venture Group as well as a handful of angel investors. $8M / Series C / Mar 01, 2013
See all 15 investments →

Co-Investors

Pioneer Square Labs

About Pioneer Square Labs

VC Fund · Seattle, United States

Pioneer Square Labs is a studio that creates and launches technology startups. They provide market research, concept validation, engineering, data science, visual, UX design, and product management services. They also provide recruiting, fundraising, marketing, company formation, finance, operations, legal, and HR services.

Pioneer Square Labs Contacts

NameEmailPhoneSocials
Ansel Santosa
Ansel Santosa Senior Software Engineer
Ben Gilbert
Ben Gilbert Co-Founder and Managing Director
David Zager
David Zager Partner and CDO
Greg Gottesman
Greg Gottesman Co-Founder & Managing Director
Julie Sandler
Julie Sandler Co-Founder, General Partner, and Managing Director

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FAQ

What does Greg Gottesman invest in?

Greg Gottesman invests primarily in News, Software and Analytics startups, most often at Series C and Funding Round stage. Most of the 15 investments tracked by Shizune back companies in United States. The Investment Focus section breaks down every industry, stage and country in the portfolio.

How do I contact Greg Gottesman?

Public channels for Greg Gottesman include LinkedIn, X (Twitter) and the website linked on this profile. For a verified work email and phone number, create a free Shizune account — contact data is searched across 20+ sources and validated before delivery, so your outreach lands in the right inbox.

When did Greg Gottesman last invest?

The most recent investment recorded for Greg Gottesman closed in Sep 2025. Shizune tracks 15 investments in total for this profile, including round sizes, stages and portfolio companies, all sourced from confirmed public funding rounds and refreshed monthly.

Is Shizune's investor data accurate?

Yes — every stat on this profile is calculated from confirmed public funding rounds monitored across hundreds of sources since 2020. This profile was last refreshed in Aug 2026 and is updated monthly. Spotted something off? Use the “Suggest an edit” link near the top of the page.

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