Pioneer Square Labs

Pioneer Square Labs, established in 2015 and headquartered in Seattle, Washington, is a venture firm that creates and launches technology startups. It offers a wide range of services, including market research, product development, design, and recruitment, to validate and launch new ideas. Additionally, it provides operational support, such as fundraising, marketing, legal, and HR services, to help these startups grow and succeed.

Geoff Entress

Managing Director

Mike Galgon

Managing Director

Ben Gilbert

Managing Director

Greg Gottesman

Managing Director

Ben Rush

Senior Associate

Matt Wang

Principal

25 past transactions

SingleFile Technologies

Series A in 2025
SingleFile Technologies develops legal and compliance management software for companies and law firms. Its platform streamlines administrative tasks such as report filing, record maintenance, and deadline tracking, helping users stay organized, efficient, and compliant with legal procedures.

KamiwazaAI

Seed Round in 2025
KamiwazaAI specializes in providing scalable artificial intelligence solutions, catering to diverse computing environments such as cloud, core, and edge. Their open-source coding platform facilitates the development of applications and server management, boasting features like enhanced deployment and configuration management, advanced error handling and logging, scalability, and flexibility. This enables developers to optimize performance and efficiency through streamlined model configuration deployment processes.

Potato AI

Pre Seed Round in 2024
AI research assistant for biology.

Overland AI

Seed Round in 2024
Overland AI develops artificial intelligence-based autonomous navigation systems for off-road vehicles. Its modular software uses machine learning and robotic technologies, enabling autonomous operation in challenging terrains like mines, construction sites, and disaster zones, primarily serving defense and national security sectors.

Enzzo

Seed Round in 2024
Enzzo is a technology company that employs artificial intelligence to facilitate and accelerate the development of hardware products. It assists businesses in defining their product specifications, mitigating risks, and fostering collaborative work environments, from initial requirements to final product realization.

Recurrent

Series A in 2024
Recurrent Motors, Inc. specializes in analyzing electric vehicle (EV) batteries and providing detailed reports that assist car dealers and private buyers in purchasing used electric cars. Founded in 2020 and based in Seattle, Washington, the company offers tools that assess battery health, life expectancy, and current maximum range of EVs, addressing the complexities involved in understanding these factors as vehicles age. By delivering non-invasive tests and leveraging a national database of vehicle data and history, Recurrent enables informed decision-making for both dealers and consumers. Additionally, the company provides personalized monthly battery analyses for EV owners, enhancing their understanding of their vehicles' performance over time.

Maximal Learning

Seed Round in 2023
Maximal Learning operates an educational platform that employs artificial intelligence to tailor learning experiences for students of all ages. Its goal is to help each student reach their full potential by planning and tracking assignments and activities.

Otis

Pre Seed Round in 2023
Otis is built for part-time employees and independent contractors.

LifeAt

Seed Round in 2023
LifeAt develops modular productivity software and virtual study spaces designed to help users sustain focus and manage their work more efficiently. The platform combines practical productivity management tools with immersive environments featuring calming landscapes, music, and timed breaks to reduce focus drift. By pairing workflow features with ambient experiences, LifeAt supports individuals in studying or working more effectively and maintaining concentration across sessions.

Satellite IM

Seed Round in 2022
Satellite IM utilizes leading decentralization and encryption technology to provide a platform to build extensible apps.

Hola Cash

Venture Round in 2021
Hola Cash is a pioneering payment platform in Latin America that offers a comprehensive checkout solution, integrating various payment methods to enhance transaction efficiency. The platform enables users to make payments to friends, merchants, and stores without relying on cash or cards, thus simplifying the payment process. Hola Cash focuses on preventing fraud and providing a seamless one-click checkout experience through a single integration, which reduces costs and complexities for merchants while delivering a fast and standardized experience for consumers. By facilitating money transfers and streamlining transactions, Hola Cash aims to make digital payments more accessible and rewarding for users across the region.

Boundless Immigration

Series B in 2021
Boundless Immigration provides an immigration service platform that blends software tools with expert legal guidance to simplify immigration for individuals, families, and businesses. Founded in 2017 and based in Seattle, it helps users determine the right visa or citizenship path, prepare applications, and access legal support, enabling efficient and confident navigation of migration processes.

Boundless Immigration

Series A in 2020
Boundless Immigration provides an immigration service platform that blends software tools with expert legal guidance to simplify immigration for individuals, families, and businesses. Founded in 2017 and based in Seattle, it helps users determine the right visa or citizenship path, prepare applications, and access legal support, enabling efficient and confident navigation of migration processes.

JetClosing

Series B in 2020
JetClosing, Inc. is a digital title and escrow company focused on streamlining the real estate closing process. Established in 2016 and headquartered in Seattle, Washington, with an additional office in Austin, Texas, JetClosing aims to enhance transparency, security, and efficiency in property transactions. The company's software application systematically captures every aspect of the closing process, ensuring accountability and providing timely insights to real estate professionals, including buyers, sellers, agents, lenders, and borrowers. With a growing presence across several states, including Arizona, Colorado, Florida, Nevada, Pennsylvania, Texas, and Washington, JetClosing is committed to transforming the traditional title and escrow services through innovative technology and a team of experienced industry professionals.

Archera

Seed Round in 2020
Archera is an information technology company that specializes in cloud cost optimization, particularly for Amazon Web Services and Microsoft Azure. The company has developed a cloud-based financial management platform that automates the processes of purchasing, renewing, and exchanging EC2 reserved instances and committed use reservations. Archera's platform focuses on managing and mitigating risks associated with cloud expenditures by building accurate forecasts, identifying opportunities for right-sizing and modernization, and executing optimal commitment plans. Additionally, it provides a safeguard for cloud commitments through guaranteed buybacks, enabling customers to achieve significant savings in both time and costs.

Hola Cash

Seed Round in 2020
Hola Cash is a pioneering payment platform in Latin America that offers a comprehensive checkout solution, integrating various payment methods to enhance transaction efficiency. The platform enables users to make payments to friends, merchants, and stores without relying on cash or cards, thus simplifying the payment process. Hola Cash focuses on preventing fraud and providing a seamless one-click checkout experience through a single integration, which reduces costs and complexities for merchants while delivering a fast and standardized experience for consumers. By facilitating money transfers and streamlining transactions, Hola Cash aims to make digital payments more accessible and rewarding for users across the region.

Hola Cash

Pre Seed Round in 2019
Hola Cash is a pioneering payment platform in Latin America that offers a comprehensive checkout solution, integrating various payment methods to enhance transaction efficiency. The platform enables users to make payments to friends, merchants, and stores without relying on cash or cards, thus simplifying the payment process. Hola Cash focuses on preventing fraud and providing a seamless one-click checkout experience through a single integration, which reduces costs and complexities for merchants while delivering a fast and standardized experience for consumers. By facilitating money transfers and streamlining transactions, Hola Cash aims to make digital payments more accessible and rewarding for users across the region.

Boundless Immigration

Series A in 2019
Boundless Immigration provides an immigration service platform that blends software tools with expert legal guidance to simplify immigration for individuals, families, and businesses. Founded in 2017 and based in Seattle, it helps users determine the right visa or citizenship path, prepare applications, and access legal support, enabling efficient and confident navigation of migration processes.

BigBox VR

Seed Round in 2018
BigBox VR, Inc. is a virtual reality game development company based in Seattle, specializing in creating immersive online multiplayer VR experiences. Founded in 2016 by experienced game industry entrepreneurs with a history of successful projects at major companies like Valve, Disney, Sony, and Microsoft, BigBox VR aims to revolutionize VR gaming by integrating platform-defining titles, social communities, and competitive play into a cohesive esports ecosystem. The company's flagship game, POPULATION: ONE, launched in 2019, features innovative gameplay mechanics that allow players to climb and fly within a fully realized virtual environment. Through its focus on high-definition, 360-degree experiences, BigBox VR strives to enhance the overall VR gaming experience for players.

Gradient.io

Seed Round in 2018
Gradient.io is an intelligent insights platform designed specifically for Amazon, utilizing proprietary machine learning technology to enhance brands' digital point-of-sale presence. The company's offerings include Gradient Digital Shelf, Gradient Score, Gradient Dynamics, and Gradient Compete, which collectively empower brands to optimize their visibility and performance on the Amazon Marketplace. By measuring a brand's digital presence in comparison to competitors within specific categories, Gradient.io helps businesses improve their search result rankings and maximize customer conversion rates. This approach enables brands to fully leverage the potential of their Amazon presence, driving increased online sales and competitive advantage.

NextStep

Seed Round in 2018
NextStep is an information technology company that provides training and job placement through a mobile and web platform, enabling users to manage staff and place them in appropriate positions. The platform supports online learning and hiring, including a certified nursing assistant training and placement program, and recruits, trains, and places workers for entry-level healthcare jobs such as community health workers, home health aides, and medical assistants. Founded in 2018 and based in Seattle, Washington, NextStep aims to help workers re-skill affordably and to assist healthcare employers in finding skilled employees.

Boltive

Venture Round in 2018
Boltive safeguards advertisers and publishers from harmful ads. Its platform shields against invasive, malicious, or offensive ads, protecting user experience and recovering lost revenues.

JetClosing

Venture Round in 2017
JetClosing, Inc. is a digital title and escrow company focused on streamlining the real estate closing process. Established in 2016 and headquartered in Seattle, Washington, with an additional office in Austin, Texas, JetClosing aims to enhance transparency, security, and efficiency in property transactions. The company's software application systematically captures every aspect of the closing process, ensuring accountability and providing timely insights to real estate professionals, including buyers, sellers, agents, lenders, and borrowers. With a growing presence across several states, including Arizona, Colorado, Florida, Nevada, Pennsylvania, Texas, and Washington, JetClosing is committed to transforming the traditional title and escrow services through innovative technology and a team of experienced industry professionals.

Gumshoe AI

Gumshoe AI is revolutionizing how companies use AI-powered search.
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