How many investments has Pioneer Square Labs made?

Pioneer Square Labs has 66 tracked investments, 3 of which have exited, including 5 dated in the last 24 months.

What stage does Pioneer Square Labs invest at?

Pioneer Square Labs invests at the Pre-Seed, Seed, Series A, Series B stages.

What sectors does Pioneer Square Labs focus on?

Pioneer Square Labs focuses on AI & Machine Learning, Sector Agnostic.

Where is Pioneer Square Labs located?

Pioneer Square Labs is headquartered in Seattle, US.

Who does Pioneer Square Labs co-invest with?

Pioneer Square Labs most often shares deals with Ascend Venture Capital, Madrona Venture Group, SeaChange, among 118 tracked co-investors.

Pioneer Square Labs

Venture studiooperating company · company profile

Seattle · Pre-Seed–Series B · 15 people tracked

Also known as PIONEER SQUARE INVESTMENT ADVISOR, LLC

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Investment thesis

Pioneer Square Labs operates as a startup studio and venture capital fund, partnering with founders to build world-changing companies by combining exceptional founders, innovative ideas, and investment capital.

Invests inAI & Machine LearningSector AgnosticSeattle United States

Source: firm website, verified Sep 29, 2026.

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Stage

Pre-Seed–Series B

Seattle, WA, US

Instruments

Equity

Founded

2015

Last 12 months

2 investments

Private fund assets

$180M

VC funds

Tracked investments

Unicorns

Acquisitions

Team · 15 people

from the firm's website & public directories

Vivek Ladsariya· Managing Director at PSL; General Partner of PSL Ventures

Vivek Ladsariya is a Managing Director at PSL and General Partner of PSL Ventures, where he leads pre-seed and seed investments from the firm's $100 million Fund II, backing Pacific Northwest technology companies. He previously was a General Partner at SineWave Ventures in San Francisco and earlier invested while at Fenox. A former multi-time founder, he started GameGarage and Moyyer Secondary Markets, and holds a B.S. in Electrical Engineering from the University of Mumbai and an MBA from the Yale School of Management.

Geoff Entress· Managing Director and Co-Founder· Pacific Northwestin 𝕏

Geoff Entress is a Managing Director and Co-Founder of PSL, and was previously a venture partner with Voyager Capital and Madrona Venture Group. He has been an active angel investor in the Pacific Northwest, investing in more than 200 private companies over two decades. A former securities lawyer and financial analyst, he held roles at firms including Perkins Coie, Jones Day, Salomon Brothers and Mellon Bank, and holds degrees from the University of Michigan Law School, Carnegie Mellon's Tepper School of Business and the University of Notre Dame.

Greg Gottesman· Managing Director and Co-Founder· Greater Seattle Areain 𝕏

Co-Chair, also Managing Director at Pioneer Square Labs.

David Zager· Partner· Seattle, Washingtonin 𝕏

David Zager is a Partner at Pioneer Square Labs, where he has led product, visual, and business design since the studio was founded in 2015. He works with founders on product and brand strategy across the portfolio. Before PSL, he studied Visual Communication at the University of Washington and founded two digital product studios, one of which was acquired.

Julie Sander· Managing Director· Seattle, Washingtonin 𝕏

Julie Sander is a Venture Partner at Pioneer Square Labs and co-founding general partner of PSL Ventures, which focuses on pre-seed and seed investments in Pacific Northwest technology startups across vertical AI, productivity, logistics, fintech, and the future of work. Previously a partner at Madrona Venture Group, she led investments in companies including Integris and Julep, and worked on the founding of Rover.com. Sander holds a Bachelor's and Master's degree in Psychology from Stanford University and an MBA from Harvard Business School, and serves as a lecturer in entrepreneurship at the UW Foster School of Business.

Alex Ray· Principal· Bremen, Bremen, Germanyin

Alex Ray is a Principal at PSL, where he works with Greg Gottesman across the firm's activities, supporting existing companies and helping create new ones. He previously worked in McKinsey & Company's Leap business-building practice helping large companies launch startups, and has been a two-time founder (backed once by Y Combinator) as well as an Associate at Oxbow Ventures. He is a full stack developer focused on ideas that apply frontier technologies such as machine learning and generative AI in accessible ways.

Matt Wang· Principal

Ben Gilbert· Venture Partner· Seattle, Washingtonin 𝕏

Ben Gilbert is a Venture Partner at PSL and co-founder and co-host of the Acquired podcast, which produces long-form episodes about company histories and strategies. He previously worked in product management at Microsoft, where he shipped the first version of Office for iPad and ran the company's grassroots innovation program, The Garage, and earlier built the productivity app "SeizeTheDay" as an independent iPhone developer. He holds a BS in Computer Science and Engineering from The Ohio State University.

Andrea Leach· Office Manager and Administrative Assistant· Seattlein

Andrea Leach joined Pioneer Square Labs in November 2021 as Office Manager and Administrative Assistant. She previously spent six and a half years at the SaaS company Pike13, handling administration and company culture from its startup phase through acquisition. A Washington native, she graduated from the University of Washington in 2003.

Caitlin Sowers· Product Design Engineer· Seattlein

Caitlin Sowers is a product design engineer focused on early-stage work, collaborating with founders and engineers to translate ideas into UI. She previously worked at Salt AI, where she helped build a visual development platform for designing and deploying AI workflows, and earlier designed products across startups and agencies. In 2025 she moved from Vancouver to Seattle to join Pioneer Square Labs.

Dani Johnson· Recruiting

Eugene Liao· Controller· Seattle, Washington, United Statesin

Eugene Liao is the Controller at Pioneer Square Labs. He has over 11 years of experience in public and venture capital accounting, with a background spanning audit, business valuation, and venture capital investments. His work has included SEC reporting, internal controls, financial planning and reporting, and the supervision and training of accounting staff.

Malaika Brown· Executive Assistant· Bellevue, Washington, United Statesin

Malaika Brown works at Pioneer Square Labs, focusing on people and relationship-oriented roles across the nonprofit and tech sectors. She started her career at the YMCA in community impact and fundraising, then spent six years at Facebook as a Recruiting Coordination Manager supporting high-growth teams and building candidate-focused hiring processes.

Palvi Mehta· CFO and Operating Partner· Greater Seattle Areain

Palvi Mehta is the CFO and Operating Partner at Pioneer Square Labs, where she leads finance and operations. She previously served as CFO at ExtraHop Networks, NewPath Networks, and RadioFrame Networks, and started her career as a CPA and auditor at Ernst & Young. She graduated Summa Cum Laude from the University of California, Berkeley with a degree in business focused on finance and accounting.

T.A. McCann· Managing Director· Seattle, Washingtonin 𝕏

T.A. McCann is a repeat entrepreneur who founded and led Senosis (acquired by Google), Gist (acquired by Blackberry), and marketing analytics company Rival IQ. He previously served as an entrepreneur-in-residence at Polaris Venture Partners and at Vulcan Capital, where he built Vulcan Labs, and held senior roles at Microsoft leading the Exchange and Mobile Services divisions. He is also an adjunct professor at the University of Washington Foster School of Business and holds a mechanical engineering degree from Purdue University.

Founder mafia

The Pioneer Square Labs mafia →

17 people who came through Pioneer Square Labs went on to found or lead other companies.

Mike GalgonManaging DirectorFounded Pioneer Square Labs +1 Ben GilbertVenture PartnerFounded Acquired +1 Robert SchulteEntrepreneur in ResidenceFounded Lumatax +1 Todd SawickiEIRFounded Gumshoe AI +1 Trip EdwardsSpinout LeadFounded Vinny +1 Greg GottesmanManaging Director and Co-FounderFounded Pioneer Square Labs Allison HarrEntrepreneur in ResidenceFounded Gemma Labs Julie SanderManaging DirectorFounded Pioneer Square Labs Alex RayPrincipalFounded Parade Brian FiocaPrincipal AI EngineerFounded RescueTime Zoe SheillSoftware Engineering/Data Science Intern (Yearlong)Founded Baseline AI Sean FlynnEntrepreneur In ResidenceFounded Single File

+ 5 more →

What they invest in

from 48 of 66 portfolio companies

SaaS ×29AI & Machine Learning ×27Enterprise Software ×15Data & Infrastructure ×8Fintech ×8Marketing Tech ×8Future of Work ×5AdTech ×4

HQs:United States×40

Who they back

founder profiles across 23 portfolio companies

39%

solo founders

9 of 23 mapped founding teams

34%

repeat founders

of 35 founders with career history

Founding team size:solo founder×92 founders×53 founders×44+ founders×5

Where their founders studiedfrom 34 founders with education data

University of Washington ×3Carnegie Mellon University ×2Duke University ×2Harvard Business School ×2Harvard University ×2Purdue University ×2Stanford University ×2University of Arkansas ×2

What their founders studiedfrom 32 founders with field-of-study data

Engineering ×9Computer Science ×8Business & Management ×4Economics ×3Finance & Accounting ×2Mathematics & Statistics ×2Physics ×2Politics & Policy ×2

Where their founders worked beforefrom 35 founders with career history

Microsoft ×5University of Washington ×4Foursquare ×3Airbnb ×2Blue Origin ×2Convoy Inc ×2Fortive ×2Pioneer Square Labs ×2

Accelerator rootsportfolio companies that came through a program

Y Combinator ×2

5 founders hold a PhD · 5 hold an MBA (of 34 with degree data)

Investments · 66 tracked

founders shown can be your intro path

By year:2026 · 2 2025 · 2 2024 · 2 2023 · 1 2022 · 1 2021 · 1 2020 · 1 2019 · 2 2018 · 3 2016 · 3 2015 · 2 2013 · 121 dated

Single Filesinglefile.io in✓ verified

SingleFile provides a platform for managing entity compliance across multiple U.S. states, combining automated deadline tracking, registered agent coverage, and state filing services.

AI & Machine LearningFintechGovTechLegalTechSaaSSeattle, US

Sean Flynn(Founder)in

Co-investorsFoundry LegalTech

Ad Lightningadlightning.comApr 2018 · $2M

Boltive provides an independent governance engine that evaluates autonomous agents, creatives, and inventory in advertising transactions to ensure compliance with defined business, security, and quality rules.

AdTechAI & Machine LearningCybersecuritySaaSSeattle, US

Pamela Slea(Chief Executive Officer)inChristine Desrosiers(Chief Product Officer)in Catherine Mietek(Chief Marketing Officer)in KC Reaney(Chief Technology Officer)inMICHAEL GALGON(Executive Officer, Director)SCOTT MOORE(Executive Officer, Director, Promoter)

Co-investorsR/GA Ventures

AG2ag2.ai

AG2 provides an open-source runtime and platform for building, orchestrating, and running systems of AI agents that operate together as a coordinated AI workforce.

AI & Machine LearningDeveloper ToolsEnterprise Software

Qingyun Wu(Founder)in

Ampdampd.io in 𝕏Pre-Seed · Jan 2016 · $1M

Ampd provides data-led marketing solutions for commerce marketers, helping brands measure and optimize paid traffic performance across retail platforms like Amazon, Walmart, Meta, TikTok, and Target.

AdTechAI & Machine LearningData & InfrastructureMarketing TechRetail TechSeattle, US

Joshua Gebhardt(CEO & Co-Founder)in Brandon Nutter(CTO & Co-Founder)in

Co-investorsGeekdom RC Ventures Techstars Wisemont Capital

Amperityamperity.comSeries A · Feb 2016 · $9M

Amperity provides a customer data foundation that unifies fragmented customer data into a single source of truth, giving marketing and analytics teams and AI agents a complete view of each customer.

AI & Machine LearningData & InfrastructureMarketing TechSeattle, US

Derek Slager(Founder)Kabir Shahani(Founder)inAmy Pelly(Executive Officer)in

Board Matt McIlwain(Director)Rajeev Singh(Director)Kelly Wright(Director)

Co-investorsDeclaration Partners Foundation Capital FUSE General Catalyst Greycroft Highsage Ventures +4 more

Anchorheadbuildwithglue.com in

An open-source design editor that allows developers and AI coding agents to collaborate on creating, modifying, and deploying UI components in real time, with changes directly converted to production code.

Advanced ManufacturingDeveloper ToolsEnterprise SoftwareRoboticsSan Francisco, US

Perbhat Kumar(CEO)inTejas Priyadarshi

Co-investorsBlast.Club imec.istart Y Combinator Abstract Ventures

AppViralityappvirality.com in 𝕏Seed · Jan 2015 · $470K

AppVirality provides tools to build, launch, automate, and track refer-a-friend referral marketing campaigns for mobile apps and SaaS products.

AdTechMarketing TechSaaSSan Francisco, US

Ramakoteswarrao Papineni(Executive Officer, Director)Laxman Papineni(Executive Officer, Director)in

Archeraarchera.ai in

Archera provides a management platform and insurance/financing products that help organizations purchase public cloud resources with reduced financial risk and optimized costs through automated cost transparency and discount optimization.

Cloud ComputingEnterprise SoftwareFintechSaaS

Aran Khanna(Founder)inNikhil Khanna(Founder)in

Co-investorsAmplify Partners Ridge Ventures

Arrivedarrived.com in 𝕏

Arrived enables individuals to invest in residential rental properties by purchasing fractional shares starting at $100.

B2B MarketplacesFintechMarketplacesPropTechSeattle, US

Ryan Frazier(Founder)in Kenny Cason(Founder)in Cameron Wu(VP of Investments)inJoel Mezistrano(Executive Officer)Alejandro Chouza(Founder)Kenneth Cason(Founder)

Co-investorsForerunner Ventures Salesforce Ventures Bezos Expeditions Core Venture Capital Good Friends Tactile Ventures +7 more

BigBox VRbigboxvr.com in 𝕏Aug 2018

Big Box VR is a virtual reality game studio behind POPULATION: ONE, a squad-based VR battle royale featuring a vertical combat system that lets players climb, fly, and fight across the map.

GamingSeattle, US

Gabe Brown(Director)in Chia Chin Lee(Executive Officer, Director)in

Board Jacob Mullins(Director)in

Co-investorsGraph Ventures GSR Ventures Outpost Capital Shasta Ventures

Boltiveboltive.com in

Boltive provides ad security technology that detects and blocks malicious, deceptive, and non-compliant ads in real time across web, mobile, and in-app environments before they reach users.

AdTechAI & Machine LearningCybersecurityMarketing TechSaaS

Pamela Slea(Chief Executive Officer)inChristine Desrosiers(Chief Product Officer)in Catherine Mietek(Chief Marketing Officer)in KC Reaney(Chief Technology Officer)in

Co-investorsFlying Fish Ventures SeaChange Wharton Alumni Angels

Boundlessboundless.com in 𝕏Mar 2019 · $25M

Boundless provides U.S. immigration services that combine software with in-house legal review to help applicants prepare and submit family green card, employment-based, O-1, and EB-1 visa applications.

LegalTechSaaSSeattle, US

Xiao Wang(Founder)in

Board Amy McCullough(Director)in Greg Gottesman(Director)in Brad Feld(Director)in

Co-investorsAlumni Ventures Escalate Capital Partners Forefront Venture Foundry NextView Ventures Trilogy Equity Partners +6 more

Boundlessboundless.network in 𝕏

Boundless aggregates underutilized GPU capacity from distributed operators to provide lower-cost compute infrastructure for AI inference, training, and evaluations.

AI & Machine LearningCloud ComputingData & Infrastructure

Brian Retford(Founder)Dee Coakley(Founder)Doug Rand(Founder)Eamon Leonard(Founder)Emily Castles(Founder)Frank Laub(Founder)

Co-investorsLvna Capital Ada Ventures Adapt Ventures Forefront Venture Foundry IDEA Fund Partners

Certivocertivo.com in

Certivo is a supply chain compliance platform that automatically collects supplier documentation, monitors certificate changes and expirations, and reports an organization's compliance posture.

AI & Machine LearningEnterprise SoftwareSaaS

Co-investorsSuffolk Technologies Pioneer Square Ventures

Dance Churchdancechurch.com

Kate Wallich(Founder)in

Co-investorsAlumni Ventures Crush Ventures Graham Walker Venture MaC Venture Capital

Dropzonedropzone.ai in 𝕏

Dropzone AI builds AI agents that investigate security alerts, hunt threats, and respond to cyberattacks for security teams and organizations.

AI & Machine LearningCybersecurityEnterprise Software

Edward Wu(Founder)in

Co-investorsDecibel Partners In-Q-Tel Madrona Venture Group Theory Ventures Pioneer Square Ventures Redpoint Ventures

EasyPosteasypost.com in 𝕏Jun 2013

EasyPost provides a RESTful API platform that simplifies shipping and logistics operations for businesses.

AI & Machine LearningEnterprise SoftwareLogistics & Supply ChainSaaSSan Francisco, US

Jarrett Streebin(Title)inJon Calhoun Rahul Vohra(Investor)inMichelle King(Vice President, People \u0026 Culture)Kaumana Rindlisbacher(Enterprise Account Executive)Heather Sherfey(Talent Acquisition Manager)

Co-investors137 Ventures Acequia Capital (AceCap)Bow Capital Eastward Capital Partners FundersClub Garage Capital +44 more

Enzzoenzzo.ai in 𝕏

Enzzo is an AI product-development platform that helps product companies define pipelines, automate workflows, and generate artifacts such as requirements, briefs, specs, competitive analyses, concept images, and bill-of-materials estimates.

AI & Machine LearningEnterprise SoftwareSaaSSeattle, US

Ford Davidson(Founder)

Co-investorsUnlock Venture Partners

Gradientgradientcomfort.com in 𝕏

Gradient manufactures a window-mounted 120V heat pump for residential heating and cooling that installs without drilling or refrigerant handling.

CleantechClimate TechHardwarePropTechSan Francisco, US

Vince Romanin(Founder)in

Co-investorsAt One Ventures Autodesk Foundation Azolla Ventures Climate Investment Collaborative Fund Dangerous Ventures +6 more

Gumshoe AIgumshoe.ai in 𝕏May 2025 · $2M

Gumshoe is an AI visibility platform that monitors how AI search tools recommend products and discuss brands, enabling marketers to understand and influence brand perception across major AI models.

AI & Machine LearningMarketing TechSaaSSeattle, US

Todd Sawicki(Co-founder)inPatrick O'Donnell(Co-founder)in

Co-investorsAscend Venture Capital GHARAGE Ventures Hawke Ventures OpenSky Ventures

House Whisperhousewhisper.ai in

HouseWhisper provides an AI platform that assists real estate agents with lead management and client follow-up through conversational AI, allowing agents to extend personalized communication at scale without changing their existing workflows.

AI & Machine LearningPropTechSaaSSeattle, US

Luis Poggi(Founder)in Alex Kutner(Founder)in Spencer Rascoff(Founder)in

Co-investorsIntegra Groupe Mayfield Fund

Iterativelyiterative.ly 𝕏acquired by Amplitude · May 2021

Amplitude provides a customer data platform that unifies customer information across touchpoints and enables teams to segment audiences, activate personalized experiences, and monitor data quality for product and marketing teams.

AI & Machine LearningData & InfrastructureMarketing TechSaaS

Co-investorsAscend Venture Capital Fika Fika Ventures Gradient Ventures PSL Ventures

Joonjoon.com in 𝕏

Joon provides app-based 1-1 online therapy delivered by licensed therapists for youth ages 13-26 and their families.

Digital HealthHealthtechMental Health

Emily Pesce(CEO)

Co-investorsCity Light Route 66 Ventures

Kamiwazakamiwaza.ai inDec 2024

Kamiwaza offers a distributed AI orchestration platform that processes data where it resides, allowing enterprises to deploy AI without centralizing data or compromising security.

AI & Machine LearningData & InfrastructureEnterprise SoftwareGovTechSilverthorne, US

Matthew Wallace(Executive Officer, Director)inLuke Matthew Norris(Executive Officer, Director)

Co-investorsAscend Venture Capital Citta Capital FirstMile Ventures Greater Colorado Venture Fund S3 Ventures Ascend +2 more

LifeAtlifeat.com in 𝕏Seed

LifeAt provides desktop software that displays ambient scenes and planning tools on a second monitor to help users maintain focus and organize their work.

ConsumerFuture of WorkSaaSWellness & FitnessSan Francisco, US

Devin Ajimine(CEO)inMarisa Chentakul(Cofounder)Ashika Mulagada(Cofounder)in Pouya Rad(Cofounder)inMarisa C(Founder)

Co-investorsPack Ventures Pioneer TRAC (Third Round Analytics Capital)Y Combinator Z Venture Capital Goodwater Capital +1 more

LoansIntelloansintel.com

Octus provides credit intelligence, structured data, and workflow tools covering leveraged loans, high-yield bonds, and private credit across the credit lifecycle from origination to distressed debt.

AI & Machine LearningData & InfrastructureFintech

Lumataxlumatax.com in 𝕏

LumaTax is a platform that automates US and Canadian sales tax compliance, helping businesses manage nexus registration, tax filings, and remittance across multiple jurisdictions.

E-commerceFintechSaaSSeattle, US

Robert Schulte(Founder)inFergal Garvey(Founder)Michael Glover(Founder)Stefan Mladenovic(Founder)

BoardChuck Stonecipher(Director)in Gregory Gottesman(Director)in

Co-investorsCowboy Ventures Gaingels Madrona Venture Group Pioneer Square Ventures Trilogy Equity Partners

Meeting Flowmeetingflow.com in 𝕏Acquired

Meetingflow is an AI meeting assistant for customer-facing teams that provides automatic note-taking, meeting summaries, a meeting-focused AI chat copilot, collaborative meeting plans, and CRM updates.

AI & Machine LearningEnterprise SoftwareFuture of WorkSaaSSales TechSeattle, US

Co-investorsAI2 Incubator Allen Institute for AI (AI2) Incubator Ascend Venture Capital Future Africa Think+ Ventures Management, Llc PSL Ventures

Olis Roboticsolisrobotics.com in

Olis Robotics provides remote monitoring, control, and troubleshooting solutions for industrial robots, serving over 50% of the global installed industrial robot fleet.

Advanced ManufacturingDeep TechEnterprise SoftwareRoboticsSeattle, US

Co-investorsAlliance of Angels SeaChange Tectonic Ventures The W Fund Ubiquity Ventures PSL Ventures

Overland Aioverland.ai

Overland AI develops ground autonomy solutions for military vehicles and land operations, enabling autonomous mobility without human operators.

AI & Machine LearningDefense TechRoboticsSeattle, US

Byron Boots(Founder)inStephanie Bonk(Founder)inGreg Okopal(Founder)inJonathan Fink(Executive Officer)

BoardChristopher Morales(Director)

Co-investors8VC Alumni Ventures Ascend Venture Capital Cubit Capital OUP (Osage University Partners)Overmatch +7 more

Panda AI inSeed · Aug 2020 · $3M

Seattle, US

Aaron Goldfeder(Executive Officer, Director, Promoter)Michael Galgon(Director)Yue Ning(Executive Officer, Director, Promoter)

Co-investorsUnlock Venture Partners

PipelineDealspipelinecrm.com in 𝕏Series A · Jan 2015 · $1M

Pipeline CRM is a sales platform designed for businesses to manage customer relationships with streamlined setup and integrations.

Cloud ComputingEnterprise SoftwareSaaSSales TechSeattle, US

James P. Werlin(Executive Officer, Director, Promoter)JP Werlin in Nicholas Bertolino(Executive Officer, Director, Promoter)in

BoardMichael T. Galgon(Director)

Readread.ai in 𝕏

Read AI builds automated meeting summaries, transcripts, and action items using AI to help knowledge workers reduce time spent on meetings, emails, and messages.

AI & Machine LearningEnterprise SoftwareFuture of WorkSaaSSeattle, US

David Shim(Founder)inRobert Williams(Co-founder)inElliott Waldron(Founder)inRob Williams(Founder)Robert A. Williams(Founder)

BoardBrad Twohig(Director)

Co-investorsMadrona Venture Group IPV Smash Capital

Recurrentrecurrentauto.com in 𝕏Jan 2024

Recurrent builds software and data analytics tools to help consumers and dealerships transition to electric vehicles and optimize EV adoption.

Climate TechData & InfrastructureMobility & TransportationRetail TechSaaS

Scott Case(Founder)in

Co-investorsArcTern Ventures Ascend Venture Capital Automotive Ventures Mobility E8 Angels EnerTech Capital Goodyear Ventures +6 more

Remarkablyremarkably.io

Remarkably provides marketing business intelligence software for multifamily and apartment operators, aggregating data from property management systems, CRMs, and Google Analytics into a central view for channel performance, ROI analysis, reporting, and forecasting.

Marketing TechPropTechSaaSSeattle, US

Erina Malarkey(Executive Officer, Director, Promoter)inAnna-Lea Dieringer(Executive Officer, Director, Promoter)Thomas A McCann III(Director)

Co-investorsGaingels PSL Ventures Wildcat Venture Partners

Riplripl.com inJun 2016 · $2M

Ripl is a content creation platform that helps small businesses, real estate agents, restaurants, and nonprofits create professional social media videos and ads for platforms like Instagram, Facebook, and YouTube.

Creator EconomyMarketing TechSaaSKirkland, US

Paul Ingalls(Executive Officer, Director, Promoter)inDANA DYKSTERHUIS(Executive Officer, Director, Promoter)

Co-investorsTechstars Trilogy Equity Partners

SageOxsageox.ai in 𝕏May 2026 · $15M

SageOx builds a team-memory platform that captures decisions, discussions, and AI agent sessions and makes that context available to both people and AI assistants.

AI & Machine LearningDeveloper ToolsFuture of WorkSaaSSeattle, US

Ajit Banerjee(Founder)inMilkana Brace(Founder)in Ryan Snodgrass(Founder)in

Co-investorsCanaan Partners A.Capital Ventures Founders' Co-op

Securesecuresave.co in 𝕏

SecureSave is an employer-sponsored emergency savings account designed to help employees build and maintain financial security through automated, accessible savings tools.

FintechHR TechSaaSWellness & Fitness

Suze Orman(Co-Founder)inDevin(Co-Founder & CEO)Bassam(Co-Founder & CTO)

Co-investorsSeaChange Altos Ventures

SecureSavesecuresave.comSep 2022 · $11M

SecureSave provides employer-sponsored Emergency Savings Accounts (ESAs) that let employees automatically save from their paychecks to cover unexpected expenses.

FintechHR TechSaaS

Co-investorsAlumni Ventures Truist Ventures

Shipiumshipium.com in 𝕏

Shipium provides an AI-powered shipping platform for modern supply chains, letting retailers and shippers automate carrier selection, optimize shipping decisions, and manage execution and billing across the shipment lifecycle.

AI & Machine LearningE-commerceLogistics & Supply ChainSaaSSeattle, US

Jason Murray(Executive Officer, Director)inDavid McCormick Brown(Executive Officer, Director)

Board Julie Sandler(Director)inChuck Stonecipher(Director)in

Co-investorsGood Friends Insight Partners Trilogy Equity Partners

SingleFile Technologiessinglefile.ai inFeb 2025

SingleFile provides entity compliance management for investment organizations managing complex structures like fund vehicles, SPVs, portfolio companies, and holding companies across all U.S. states.

AI & Machine LearningEnterprise SoftwareFintechLegalTechSaaSSeattle, US

Aaron Finn(Executive Officer, Director)in

BoardJaclyn Hester(Director)Greg Gottesman(Director)Ramana Venkata(Director)

Co-investorsFoundry

Sofysofy.ai in 𝕏

Sofy is a no-code test automation platform for mobile apps that runs end-to-end testing from the CI/CD pipeline on real physical devices without requiring code.

AI & Machine LearningDeveloper ToolsSaaSBellevue, US

Syed Hamid(Founder)in

Co-investors500 Global Revolution Voyager Capital GTMfund

Starfish Spacestarfishspace.com in 𝕏

Starfish Space develops Otter, an autonomous satellite servicing vehicle that uses electric propulsion to dock with satellites for life extension and disposal.

Deep TechHardwareSpace TechTukwila, US

Trevor Bennett(Founder)in Austin Link(Founder)in

Board Morgan Beller(Director)inPeter Ortez(Director)Letitia Long(Director)

Co-investorsACTIVATE CAPITAL PARTNERS Alumni Ventures Booz Allen Ventures Carbon Denver Ventures Hypothesis +25 more

Supersuper.ai in 𝕏

Super.AI provides intelligent document processing (IDP) software that automates information extraction and downstream business processes from documents for enterprises in logistics, shipping, financial services, and technology sectors.

AI & Machine LearningData & InfrastructureEnterprise SoftwareWilmington, US

Brad Cordova(Founder)in

Co-investorsDiscovery Ventures III Gmb H & Co. KG Mosaic Ventures NFX Seaplane Ventures

TeamSenseteamsense.com in 𝕏

TeamSense is an AI-powered, text-based platform that automates attendance tracking, absence reporting, and multilingual worker communication for frontline teams, syncing with HRIS systems.

AI & Machine LearningFuture of WorkHR TechSaaSEverett, US

Sheila Stafford(Co-founder & CEO)in Alison Teegarden(Co-founder & COO)in

Board Brett Queener(Director)inSoojeong Shin Anderson(Director)

Co-investorsBonfire Ventures Gingerbread Capital Growth Warrior Capital Ingeborg Investments IrishAngels Operator Collective

Tin Cantincan.kids

Tin Can makes a Wi-Fi landline phone for children that allows voice calls only to a parent-approved contact list, blocking strangers, robocalls, and scammers.

ConsumerDirect to ConsumerHardwareSeattle, US

Graeme Chet Kittleson(Founder)inMax Blumen(Founder)inGraeme Davies(Founder)

Co-investorsCollaborative Fund Data Tech Greylock Partners Imaginary Venture Capital Marketplace Newfund Capital +2 more

Trova Triptrovatrip.com in 𝕏

TrovaTrip organizes ethical tourism experiences that prioritize meaningful connections and cultural respect.

ConsumerImpact & Social GoodMarketplacesTravel & HospitalityPortland, US

Christopher Nicholas Poggi(managing member)Brandon Bruce Denham(managing member)Nick Poggi ✈️(Founder)inLauren Schneider(Founder)inBrandon Denham(Founder)Nick Poggi(Founder)

Co-investorsElevate Capital Madrona Venture Group Oregon Venture Fund Portland Seed Fund

Wildtypewildtypefoods.comOct 2019

Wildtype grows salmon directly from fish cells using cellular agriculture, allowing production of seafood without wild-caught or farmed fish.

BiotechClimate TechFoodTechSan Francisco, US

Justin Kolbeck(Founder)inArye Elfenbein(Founder)inJustin Kolbeck Arye Elfenbein(Founder)

BoardJohn Melas-Kyriazi(Director)

Co-investorsBay Bridge Ventures Climate CRV (Charles River Ventures)Maven Ventures Mission Biocapital Root Ventures Manager, Llc S2G Investments +19 more

Yeslergoyesler.com

B2B lumber and building materials marketplace

Seattle, US

MATTHEW MEYERS(Executive Officer, Director, Promoter)MICHAEL GALGON(Executive Officer, Director)BLAKE PATTON(Director)

Co-investorsFamily Angel Management Fund SeaChange Tech Square Ventures Ascend Crosslink Capital

Zipziphq.com in 𝕏

Zip is an AI platform for enterprise procurement that automates and optimizes the B2B purchasing process from intake to payment.

AI & Machine LearningEnterprise SoftwareSaaSSan Francisco, US

Rujul Zaparde(CEO and Cofounder)in Lu Cheng(CTO and Cofounder)in Larry Diamond(Executive Officer, Director)inMartin Brooke(Executive Officer)Peter Gray(Executive Officer, Director)June Lee(Recruiting)

Co-investorsY Combinator Tiger Global Management AirAngels Alkeon Innovation Bond Capital Management CRV (Charles River Ventures)+14 more

Zuccazucca.ai in

Zucca is a product development platform for consumer packaged goods (CPG) innovation and R&D teams that connects formulas to live supplier specs, real-time costs, and regulatory constraints.

AI & Machine LearningFoodTechSaaS

Co-investorsAcre Venture Partners Mayfield Fund PSL Ventures

Other

Tracked investments with no reachable website or further public details — typically companies that wound down, renamed, or were absorbed.

555 Bryant StreetAlertiveCopperEvergreen RenewablesFelix & FidoGemmistGenbaGlowKevalaLevMaximalLearningNextStep InteractiveOutgoTally

Exits · 3

3 acquisitions · showing 1

Iterativelyacq. by Amplitude

Portfolio news

latest coverage across their companies

Starfish Space Raises $100M in Series B Funding

Starfish Space · finsmes.com · Apr 8, 2026

Certivo Raises $4M in Seed Funding

Certivo · finsmes.com · Feb 17, 2026

Overland AI Raises $100M in Funding

Overland Ai · finsmes.com · Feb 4, 2026

Tin Can Raises $3.5M Pre-Seed Funding

Tin Can · leadsontrees.com · Dec 23, 2025

Arrived Launches First-Ever 'Stock Market' for Real Estate; Raises $27 Million

Arrived · finance.yahoo.com · Nov 12, 2025

TeamSense, a Seattle-area startup that helps track employee absences, raises more cash – GeekWire

TeamSense · geekwire.com · Aug 20, 2025

Dropzone AI Secures $37M Series B, Putting AI Security Analysts on the Front Lines of Cyber Battlefield

Dropzone · finance.yahoo.com · Jul 28, 2025

Seattle startup Zucca raises $5M to help food brands launch products faster with AI – GeekWire

Zucca · geekwire.com · Jul 15, 2025

Frequently asked questions

How many investments has Pioneer Square Labs made?: Pioneer Square Labs has 66 tracked investments, 3 of which have exited, including 5 dated in the last 24 months.
What stage does Pioneer Square Labs invest at?: Pioneer Square Labs invests at the Pre-Seed, Seed, Series A, Series B stages.
What sectors does Pioneer Square Labs focus on?: Pioneer Square Labs focuses on AI & Machine Learning, Sector Agnostic.
Where is Pioneer Square Labs located?: Pioneer Square Labs is headquartered in Seattle, US.
Who does Pioneer Square Labs co-invest with?: Pioneer Square Labs most often shares deals with Ascend Venture Capital, Madrona Venture Group, SeaChange, among 118 tracked co-investors.

Media · Podcasts & interviews

featuring the team

Companies Make Companies, with Acquired FM & Pioneer Square Labs Co-Founder Ben Gilbert | Episode 37

The Ones Who Succeed · Ben Gilbert

Don’t Sleep on Seattle Startups | Vivek Ladsariya, Managing Director, Pioneer Square Labs

Carta · Vivek Ladsariya

The 5-Step, AI-Powered Startup Studio Engine. T.A. McCann @ Pioneer Square Labs

Max Pog | LP & VC Insights · T.A. McCann

Founding Rover and the business model behind Pioneer Square Labs, a conversation with Greg Gottesman

TiE Seattle · Greg Gottesman

T.A. McCann - Pioneer Square Labs - What Fuels You

What Fuels You Podcast · T.A. McCann

CLIP: Resource Nights class feat. Ben Gilbert of Pioneer Square Labs

Buerk Center · Ben Gilbert

Images

Co-investors · 53

Alumni Ventures

Alumni Ventures (AV) is a venture capital firm that co-invests alongside lead VCs in startups, backing founders with capital and access to a large investor and operator community.

Both backed · 5

Boundless Overland Ai SecureSave Starfish SpaceDance Church

$100K – $10M

Madrona Venture Group

Madrona Venture Group is a venture capital firm that backs founding teams at the seed, early, and acceleration stages, with a focus on Seattle, the Bay Area, and beyond.

Both backed · 5

Amperity Dropzone Lumatax Read Trova Trip

$2M – $10M

Techstars

Techstars is a global startup accelerator and early-stage investor that funds and mentors ambitious founders, providing $220K in capital, a three-month program, and access to a worldwide network of mentors, investors, and corporate partners.

Both backed · 3

Ampd Arrived Ripl

$220K

Foundation Capital

Foundation Capital is an early-stage venture capital firm that commits to founders at the idea stage and maintains long-term relationships with portfolio companies through their growth journey.

Both backed · 3

Amperity Boundless EasyPost

$250K – $15M

Foundry

Foundry invests in early-stage startups and venture funds across multiple sectors. The firm builds a portfolio-based network connecting portfolio companies with other investors and entrepreneurs.

Both backed · 3

Boundless Single File SingleFile Technologies

$250K – $15M

Spark Capital

Spark Capital is a venture capital firm that partners with founders, known for early investments including leading Twitter's Series B in 2008.

Both backed · 2

EasyPost Wildtype

$500K – $25M

Founders' Co-op

Founders' Co-op is a Seattle-based early-stage venture firm backing technical founding teams building enterprise technology companies, investing at the pre-product, pre-revenue stage.

Both backed · 2

Boundless SageOx

$10K – $250K

Voyager Capital

Voyager Capital is a venture capital firm that invests in early-stage entrepreneurs across the Pacific Northwest and Western Canada, focusing on the modern economy.

Both backed · 2

Overland Ai Sofy

$1M – $4M

Andreessen Horowitz

Andreessen Horowitz (a16z) is a venture capital firm founded in 2009 by Marc Andreessen and Ben Horowitz, known for pioneering the platform model with a large team of operators supporting founders across stages.

Both backed · 1

EasyPost

$500K – $50M

Craft Ventures

Craft Ventures is a venture capital firm run by a team of former founders, operators, and investors who partner closely with founders to help build and scale technology companies.

Both backed · 1

EasyPost

$50K – $50M

Khosla Ventures

Khosla Ventures is a venture capital firm that backs bold, early-stage, technology-driven companies across deep tech and other sectors, providing hands-on 'venture assistance' to help founders build category-defining businesses.

Both backed · 1

EasyPost

$100K – $20M

Uncork Capital

Uncork Capital is a seed-stage venture firm that backs early founders, with a focus on AI-native companies driving scale and industry change.

Both backed · 1

EasyPost

$3M – $5M

▶41 more co-investors

Sound Ventures Liquid Ventures Trajectory Ventures Sherpalo Ventures AngelPad Acequia Capital (AceCap)Hyde Park Venture Partners 137 Ventures Maven Ventures Flying Fish Ventures Tunitas Ventures Geekdom Wisemont Capital Menlo Ventures Everywhere Ventures B Capital Group Eniac Ventures Quiet Capital Innovation Endeavors Maveron Threshold Ventures Kindred Ventures LOI Venture Zetta Venture Partners Peak XV Partners Shrug Capital Rocketship.vc Third Kind Venture Capital Basement Hummingbird Ventures Radical Ventures Clocktower Ventures Incisive Ventures Backed Basecamp Fund Creative Destruction Lab (CDL)Hannah Grey Ventures Panache Ventures Wave Capital Elementum Ventures Austral Capital

Firms observed investing alongside Pioneer Square Labs, from public investor directories. Shared companies are the overlap with Pioneer Square Labs's recorded portfolio.

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