# Pioneer Square Labs

> Pioneer Square Labs is a VC fund backing Artificial Intelligence and Software. See 32 investments, check sizes, portfolio and contact details. Updated Aug 2026.

- Type: VC Fund
- Location: Seattle, United States
- Total investments: 32
- Last investment: May 2026
- Lead investor: 19%
- Fund size: $20M
- Last fund: May 2023
- Last updated: Aug 2026
- LinkedIn: https://www.linkedin.com/company/pioneer-square-labs/
- X (Twitter): https://twitter.com/psl
- Website: https://psl.com
- Facebook: https://www.facebook.com/PioneerSquareLabs

Pioneer Square Labs is a studio that creates and launches technology startups. They provide market research, concept validation, engineering, data science, visual, UX design, and product management services. They also provide recruiting, fundraising, marketing, company formation, finance, operations, legal, and HR services.

## Contacts

5 contacts available for Pioneer Square Labs. Shizune tracks 9 team members at Pioneer Square Labs. Sign up free to unlock them: https://app.shizune.co/sign-up/investor-profiles/find-team-emails/pioneer-square-labs?utm_source=investor_profile

## Investment focus

### Industry

| Industry | Investments | Share |
| --- | --- | --- |
| Artificial Intelligence | 8 | 25% |
| Software | 7 | 22% |
| Information Technology | 4 | 13% |
| Education | 3 | 9% |
| Machine Learning | 3 | 9% |

52 industries tracked in total.

### Stage

| Stage | Investments | Share |
| --- | --- | --- |
| Seed | 14 | 44% |
| Pre-Seed | 5 | 16% |
| Series B | 3 | 9% |
| Series A | 2 | 6% |
| Funding Round | 2 | 6% |

### Country

| Country | Investments | Share |
| --- | --- | --- |
| United States | 19 | 59% |
| Mexico | 1 | 3% |

## Team

| Name | Title | Investments | Profile |
| --- | --- | --- | --- |
| Ansel Santosa | Senior Software Engineer | 0 | https://shizune.co/investors/profile/ansel-santosa |
| Ben Gilbert | Co-Founder and Managing Director | 5 | https://shizune.co/investors/profile/benjamin-gilbert |
| David Zager | Partner and CDO | 0 | https://shizune.co/investors/profile/david-zager |
| Greg Gottesman | Co-Founder & Managing Director | 15 | https://shizune.co/investors/profile/greg-gottesman |
| Julie Sandler | Co-Founder, General Partner, and Managing Director | 11 | https://shizune.co/investors/profile/julie-sandler |

## Investments

| Company | Description | Amount | Stage | Date | Website |
| --- | --- | --- | --- | --- | --- |
| SageOx | SageOx develops context infrastructure that keeps humans and AI agents aligned around shared decisions and knowledge. The platform captures discussions, coding sessions, and assistant chats, then converts them into structured, searchable team memory. SageOx injects this context into AI coding agents and assistants at the start of each session sothey can follow team conventions and prior decisions. Its Ox Dot device records in‑room conversations, while the Ox CLI connects repositories and agent workflows to shared context. Ox MCP links ChatGPT, Claude, and other MCP-compatible assistants to the same memory, and Ox Console gives teams a unified view across decisions, sessions, and recordings. | $15M | Seed | May 06, 2026 |  |
| Certivo | Certivo is an AI-powered product and regulatory compliance management platform that helps manufacturers automate, streamline, and simplify compliance with regulations such as RoHS, REACH, PFAS, and more. Our platform eliminates compliance bottlenecks, reduces risk, and accelerates market access. You can learn more at certivo.com. | $4M | Seed | Feb 17, 2026 |  |
| Casera | Casera empowers healthcare organizations with innovative case management solutions for better patient care and operational excellence. | $1M | Seed | Dec 09, 2025 |  |
| BluePill | BluePill AI platform enables brands to test products, messaging, and creative concepts in minutes. | $6M | Seed | Nov 17, 2025 |  |
| Dropzone AI | Dropzone AI’s platform delivers pre-trained autonomous AI security agents that work alongside human analysts on security operations teams. It handles the frontline work of investigating the mountain of alerts from security systems. Using cutting-edge LLMs, Dropzone’s agents perform end-to-end investigations mimicking the techniques of eliteanalysts and enable human analysts to focus on what matters the most to them and real threats. | $37M | Series B | Jul 17, 2025 |  |
| Gumshoe AI | Gumshoe AI is revolutionizing how companies use AI-powered search. | $2M | Pre-Seed | Apr 29, 2025 |  |
| SingleFile Technologies | SingleFile is an AI-powered compliance platform automating compliance filings and annual reports across 50 states for complex multi-entity organizations. The platform centralizes Secretary of State filings, annual reports, EIN applications, and service-of-process management in a single collaborative workspace designed for organizations managinglarge entity portfolios at scale.SingleFile's technology automates jurisdiction-specific requirements across all 50 states and the District of Columbia, processing thousands of filings in minutes rather than days. Services include entity formations, foreign qualifications, certificates of good standing, amendments, apostilles, and certified document retrieval.The multi-user platform enables seamless collaboration between organizations and their outside counsel or fund administrators, with audit-ready documentation and a pricing model that charges only for services performed—no per-user or per-entity fees. | $9.1M | Series A | Feb 19, 2025 |  |
| KamiwazaAI | KamiwazaAI offers scalable AI solutions for cloud, core, and edge environments. | $8.5M | Seed | Jan 09, 2025 |  |
| Potato | AI research assistant for biology. | $1M | Pre-Seed | Oct 28, 2024 |  |
| Mudstack | Mudstack is a purpose-built asset management platform for game studios and digital artists. We help game studios and art teams manage, collaborate, and ship art assets and pipelines better, faster, and with confidence. | $4M | Seed | Aug 19, 2024 |  |

10 of 32 investments shown.

## Co-investors
- [Trilogy Equity Partners](https://shizune.co/investors/profile/trilogy-equity-partnership) — VC Fund, 8 deals together
- [Foundry Group](https://shizune.co/investors/profile/foundry-group) — VC Fund, 4 deals together
- [Foundry Group](https://shizune.co/investors/profile/foundryvc) — VC Fund, 4 deals together
- [Flying Fish Partners](https://shizune.co/investors/profile/flying-fish-venture-partners) — VC Fund, 3 deals together
- [Y Combinator](https://shizune.co/investors/profile/y-combinator) — VC Fund, 3 deals together
- [Alumni Ventures](https://shizune.co/investors/profile/alumni-ventures-group) — VC Fund, 2 deals together

## Similar investors

### Similar stage
- [Antler](https://shizune.co/investors/profile/antler-be9c) — VC Fund
- [Alumni Ventures](https://shizune.co/investors/profile/alumni-ventures-group) — VC Fund
- [Right Side Capital Management](https://shizune.co/investors/profile/right-side-capital-management) — VC Fund

## FAQ

### What does Pioneer Square Labs invest in?

Pioneer Square Labs invests primarily in Artificial Intelligence, Software and Information Technology startups, most often at Seed and Pre-Seed stage. Most of the 32 investments tracked by Shizune back companies in United States. The Investment Focus section breaks down every industry, stage and country in the portfolio.

### How do I contact Pioneer Square Labs?

Public channels for Pioneer Square Labs include LinkedIn, X (Twitter) and the website linked on this profile. For a verified work email and phone number, create a free Shizune account — contact data is searched across 20+ sources and validated before delivery, so your outreach lands in the right inbox.

### Who are the partners at Pioneer Square Labs?

The team at Pioneer Square Labs includes Ansel Santosa (Senior Software Engineer), Ben Gilbert (Co-Founder and Managing Director) and David Zager (Partner and CDO), among 9 team members tracked by Shizune. The Team section lists each member with their title, investment count and links.

### Is Shizune's investor data accurate?

Yes — every stat on this profile is calculated from confirmed public funding rounds monitored across hundreds of sources since 2020. This profile was last refreshed in Aug 2026 and is updated monthly. Spotted something off? Use the “Suggest an edit” link near the top of the page.

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