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

25 past transactions

SingleFile

Series A in 2025
SingleFile Technologies develops legal and compliance management software designed to streamline administrative tasks for companies and law firms. Its software facilitates the completion of reports, the management of filings, and the maintenance of internal records, helping clients efficiently manage compliance activities. By reducing waste, minimizing errors, and preventing missed deadlines, SingleFile enables organizations to save time and maintain good standing with legal requirements.

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 specializes in the development and manufacturing of autonomous navigation technologies for off-road vehicles. The company focuses on creating artificial intelligence-based solutions that enhance navigation and transportation capabilities in mission-critical sectors, including defense and national security. By leveraging machine learning and robotic systems, Overland AI offers modular software solutions that facilitate autonomous operation in challenging environments, such as mines, construction sites, and disaster zones. Its innovations aim to enable users to navigate unimproved roads and complex terrains effectively, thereby improving operational efficiency and safety in diverse applications.

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 is an educational platform that leverages artificial intelligence to enhance the learning potential of students across all age groups, from K-12 to higher education. The company aims to provide quality educational resources tailored to help individuals achieve their personal and professional objectives. Collaborating with the Stanford Graduate School of Education, Maximal Learning focuses on research-driven methodologies that inform its approach, similar to strategies adopted by major technology firms. By utilizing AI, the platform seeks to create personalized learning experiences that promote optimal educational outcomes for each student.

Otis

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

LifeAt

Seed Round in 2023
LifeAt is a developer of modular productivity software that aims to enhance focus and productivity for its users. The company's innovative tool offers virtual workspaces featuring videos of calming landscapes and serene scenarios, creating a tranquil environment conducive to studying and working. By incorporating peaceful music and the presence of well-known influencers or celebrities, LifeAt's platform seeks to elevate the user experience and maintain concentration. The company's approach not only simplifies productivity management but also encourages users to engage in focused work while minimizing distractions.

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 is a Seattle-based company founded in 2017 that focuses on simplifying the immigration process for individuals, families, and businesses. It offers an innovative platform that empowers users to navigate the complexities of the immigration system with confidence and ease. By providing expert legal guidance and personalized support, Boundless ensures that clients have access to the necessary tools and information for their immigration journey. The company's commitment to affordability and accessibility allows users to connect with immigration lawyers and file their applications online, streamlining what can often be a challenging experience.

Boundless Immigration

Series A in 2020
Boundless Immigration is a Seattle-based company founded in 2017 that focuses on simplifying the immigration process for individuals, families, and businesses. It offers an innovative platform that empowers users to navigate the complexities of the immigration system with confidence and ease. By providing expert legal guidance and personalized support, Boundless ensures that clients have access to the necessary tools and information for their immigration journey. The company's commitment to affordability and accessibility allows users to connect with immigration lawyers and file their applications online, streamlining what can often be a challenging experience.

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 is a Seattle-based company founded in 2017 that focuses on simplifying the immigration process for individuals, families, and businesses. It offers an innovative platform that empowers users to navigate the complexities of the immigration system with confidence and ease. By providing expert legal guidance and personalized support, Boundless ensures that clients have access to the necessary tools and information for their immigration journey. The company's commitment to affordability and accessibility allows users to connect with immigration lawyers and file their applications online, streamlining what can often be a challenging experience.

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 based in Seattle, Washington, founded in 2018. It specializes in providing training and job placement services through a mobile application platform. The company's platform offers online certified nursing assistant (CNA) training and placement programs, as well as recruitment, training, and placement for various entry-level healthcare jobs such as community health workers, home health aides, and medical assistants. This enables individuals to quickly and affordably reskill themselves while helping employers in the healthcare sector find skilled employees.

Boltive

Venture Round in 2018
Boltive is a company dedicated to enhancing the integrity of digital advertising by safeguarding both advertisers and publishers from invasive advertisements. These ads, which may be heavy, malicious, or offensive, can compromise user privacy and violate regulatory standards. Boltive's innovative advertisement analytics platform addresses these issues by eliminating problematic ads and optimizing revenue streams for publishers. The platform facilitates the management of programmatic advertising, ensuring compliance and preserving brand reputation while improving audience experience. By providing tools to analyze sales data and enhance page performance, Boltive enables companies to recover lost revenue associated with non-compliant digital advertisements, thus fostering a safer and more efficient advertising ecosystem.

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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