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

Venture Partner, Co-Founder and Managing Director

Palvi Mehta

CFO and Operating Partner

Julie Sandler

Co-Founder, General Partner and Managing Director

25 past transactions

SingleFile

Series A in 2025
SingleFile Technologies offers legal and compliance management software designed to streamline administrative tasks for companies and law firms. The software facilitates the completion of reports, management of filings, and maintenance of internal records, thereby helping clients reduce waste, minimize errors, and avoid missed deadlines. By enhancing compliance activities, SingleFile enables organizations to save time and maintain good standing with legal requirements.

KamiwazaAI

Seed Round in 2025
KamiwazaAI offers scalable AI solutions for cloud, core, and edge environments.

Potato AI

Pre Seed Round in 2024
AI research assistant for biology.

Overland AI

Seed Round in 2024
Overland AI specializes in the development of autonomous navigation technology tailored for off-road vehicles. The company focuses on creating artificial intelligence-based solutions that enhance off-road autonomy, particularly for mission-critical sectors such as defense and national security. By utilizing machine learning and robotic systems, Overland AI provides modular software designed to facilitate the autonomous navigation of unimproved roads and rugged terrain. This technology enables clients to operate vehicles independently in challenging environments like mines, construction sites, and disaster zones, addressing the need for reliable transportation solutions in demanding conditions.

Enzzo

Seed Round in 2024
Enzzo is an AI-powered platform that aims to expedite and streamline the creation of innovative hardware products, from requirement generation to risk mitigation and seamless collaboration.

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 focused on harnessing artificial intelligence to enhance the learning potential of students across all age groups, including K-12 and higher education. The company collaborates with the Stanford Graduate School of Education on research initiatives to develop effective learning tools. By tailoring educational experiences to meet individual needs, Maximal Learning aims to provide quality instruction that supports both personal and professional objectives.

Otis

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

LifeAt

Seed Round in 2023
LifeAt is a company that creates modular productivity software designed to enhance focus and productivity. Its primary offering is a digital workspace that features calming landscape videos, serene scenarios, and soothing music to help users concentrate. The platform allows individuals to study or work in a virtual environment enriched by the presence of popular influencers and celebrities, providing a unique atmosphere for productivity. By integrating these elements, LifeAt aims to simplify productivity management and reduce distractions, allowing users to dedicate more time to their tasks.

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 by integrating various payment methods into a single interface. This innovative approach simplifies the payment process for merchants, allowing them to connect with multiple providers efficiently and affordably. Additionally, Hola Cash enhances the user experience by enabling fast, one-click transactions that reduce friction during the checkout process. The platform not only facilitates payments to friends, stores, and merchants without the need for cash or cards but also helps users earn rewards while streamlining their financial transactions. Through its focus on fraud prevention and accessibility, Hola Cash aims to transform the way payments are made in 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 founded in 2016 and headquartered in Seattle, Washington, with an additional office in Austin, Texas. The company specializes in streamlining the real estate closing process through its advanced software application, which enhances transparency, security, and efficiency. Operating in states including Arizona, Colorado, Florida, Nevada, Pennsylvania, Texas, and Washington, JetClosing aims to provide reliable digital title and escrow services for buyers, sellers, agents, lenders, and borrowers. By capturing and systematizing each aspect of the closing process, JetClosing ensures accountability and offers timely insights, thus enabling real estate professionals and property managers to improve productivity and optimize efficiency in their transactions.

Archera

Seed Round in 2020
Archera is an information technology company that specializes in cloud cost optimization and financial management for cloud services. The company has developed a cloud-based platform aimed at managing costs specifically for Amazon Web Services and Microsoft Azure. Archera's software automates various processes, including the purchasing, renewing, and exchanging of EC2 reserved instances and convertible reserved instances. By providing tools for building forecasts, identifying right-sizing and modernization opportunities, and executing optimal commitment plans, Archera helps customers mitigate risks associated with cloud management. Additionally, the platform offers guaranteed buybacks to protect cloud commitments, ultimately enabling organizations to save both time and money in their cloud operations.

Hola Cash

Seed Round in 2020
Hola Cash is a pioneering payment platform in Latin America that offers a comprehensive checkout solution by integrating various payment methods into a single interface. This innovative approach simplifies the payment process for merchants, allowing them to connect with multiple providers efficiently and affordably. Additionally, Hola Cash enhances the user experience by enabling fast, one-click transactions that reduce friction during the checkout process. The platform not only facilitates payments to friends, stores, and merchants without the need for cash or cards but also helps users earn rewards while streamlining their financial transactions. Through its focus on fraud prevention and accessibility, Hola Cash aims to transform the way payments are made in 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 by integrating various payment methods into a single interface. This innovative approach simplifies the payment process for merchants, allowing them to connect with multiple providers efficiently and affordably. Additionally, Hola Cash enhances the user experience by enabling fast, one-click transactions that reduce friction during the checkout process. The platform not only facilitates payments to friends, stores, and merchants without the need for cash or cards but also helps users earn rewards while streamlining their financial transactions. Through its focus on fraud prevention and accessibility, Hola Cash aims to transform the way payments are made in 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 Seattle-based company specializing in the development of virtual reality games. Founded in 2016 by experienced entrepreneurs from the gaming industry, the company focuses on creating immersive and high-definition VR experiences. BigBox VR aims to establish a vibrant esports ecosystem by combining engaging games, social communities, and competitive play. The company's notable title, POPULATION: ONE, released in 2019, features a unique FreeMotion mechanic that allows players to climb and fly in a fully interactive VR environment. Through its innovative approach, BigBox VR seeks to redefine online multiplayer gaming in the virtual reality space.

Gradient.io

Seed Round in 2018
Gradient.io is an intelligent insights platform focused on enhancing brand visibility and sales on Amazon. Utilizing proprietary machine learning technology, it offers solutions such as Gradient Digital Shelf, Gradient Score, Gradient Dynamics, and Gradient Compete. These tools enable brands to analyze and optimize their digital presence on the Amazon Marketplace, assessing their performance against competitors within specific categories. By leveraging these insights, businesses can improve their product rankings in search results, ultimately maximizing their shelf presence and increasing customer conversion rates.

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 and web-based platform. The company focuses on the healthcare sector, offering a certified nursing assistant (CNA) training program and facilitating the recruitment, training, and placement of individuals for entry-level healthcare positions, including community health workers, home health aides, and medical assistants. NextStep aims to enable individuals to quickly and affordably re-skill themselves while assisting employers in the healthcare industry in finding qualified personnel.

Boltive

Venture Round in 2018
Boltive is dedicated to safeguarding advertisers and publishers from invasive advertisements that compromise user experience and violate regulations. The company has developed an advertisement analytics platform designed to eliminate harmful, heavy, or offensive ads that may leak private data. By focusing on programmatic advertising, Boltive aims to enhance brand integrity, protect audience engagement, and recover lost revenue linked to slow-loading or non-compliant digital ads. Its solution allows companies to efficiently analyze sales data, optimize page performance, and improve overall brand productivity, thereby securing the digital advertising ecosystem from unwanted and unsafe media.

JetClosing

Venture Round in 2017
JetClosing, Inc. is a digital title and escrow company founded in 2016 and headquartered in Seattle, Washington, with an additional office in Austin, Texas. The company specializes in streamlining the real estate closing process through its advanced software application, which enhances transparency, security, and efficiency. Operating in states including Arizona, Colorado, Florida, Nevada, Pennsylvania, Texas, and Washington, JetClosing aims to provide reliable digital title and escrow services for buyers, sellers, agents, lenders, and borrowers. By capturing and systematizing each aspect of the closing process, JetClosing ensures accountability and offers timely insights, thus enabling real estate professionals and property managers to improve productivity and optimize efficiency in their transactions.

Gumshoe AI

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