Pioneer Square Labs — 2025 Investments
2 investments dated 2025 · listed companies and verified rows first · show all
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 CapitalGHARAGE VenturesHawke VenturesOpenSky Ventures
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-investorsAIStudio
Rows marked “SEC filing” are inferred from directors named on the company's SEC Form D — public regulatory data, not a portfolio list published by the firm.





