SQUADRA VENTURES
Actively deployingBaltimore · Pre-Seed–Growth · 8 people tracked
Investment thesis
Squadra applies a growth-stage mindset at the seed stage, believing that entrepreneurs need significant resources beyond capital to accelerate from early product-market fit to rapid expansion. The firm builds infrastructure and operational foundations through strategic planning, go-to-market development, and executive recruitment, leveraging deep ties to decision-makers in government and the commercial sector to position companies for sustainable scaling and future funding rounds.
Source: firm website, verified Jul 20, 2026.
Team · 8 people
from the firm's websiteFounder of Squadra Ventures in 2019, he leads investment and portfolio operations. Previously founded and sold two companies: Red Owl Analytics (cybersecurity, acquired by ForcePoint in 2017) and Berico Technologies (cloud and data analytics consulting for intelligence, acquired by Novetta in 2018). Former US Army intelligence officer with posts in Korea, Italy, Germany, Afghanistan, and NSA. Educated at West Point and Oxford University as a Marshall Scholar.
Leads finances, compliance, and fundraising at Squadra. Responsible for investor relations, portfolio valuation, and supporting founders in financial professionalization. Brings 13 years of venture capital and private equity expertise from roles at Camden Partners and Cornerstone Advisory, with background in M&A, corporate finance, and strategic planning.
Leads the National Security practice, sourcing and evaluating companies for investment and supporting federal go-to-market strategy post-investment. Served as Mid-Atlantic Regional Director at the National Security Innovation Network (DoD's technology accelerator) and as senior policy analyst at RAND Corporation. Former Marine Corps artillery officer and military legislative assistant. Currently a visiting scholar at Columbia University's Entrepreneurship Program.
Leads relationship-building and network operations between Squadra and portfolio companies. Served 33 years in the US Army, including 24 years as a Green Beret in special operations with deployments across Europe, Africa, and the Middle East. Completed career as Special Forces Warrant Officer and Pentagon advisor to US Army Special Operations Command. Holds MBA from Boston University.
Leads post-investment support for dual-use and enterprise software portfolio. Co-founder of Yet Analytics, a data interoperability and analytics company serving enterprise learning and training organizations across government and industry. Experienced community-builder with advisory board roles in startup accelerators and incubator programs. Regular contributor to industry publications and founder-focused columns.
Supports the investment team on national security and cybersecurity deals. Former strategy consultant who led DoD modernization efforts across readiness, intelligence, and cyber arenas. Worked with the National Security Innovation Network to develop regional technology ecosystems and pathways for early-stage startups engaging with DoD. Holds BS in International Economics from Georgetown and MBA from Columbia.
Manages Squadra's events, calendars, and administrative processes. Previously spent 10 years supporting executive leadership. Graduated from Colorado State University with a degree in Business and Marketing.
Works with portfolio companies from investment through exit on client engagement, partnership development, resource acceleration, and talent/tools access. Spent two decades in private equity at Camden Partners driving strategic and operational support for lower middle market companies in enterprise software, business services, and fintech. MBA graduate from University of Maryland.
What they invest in
from 4 of 16 portfolio companiesDeep Tech ×2Space Tech ×2Advanced Manufacturing ×1AgTech ×1Climate Tech ×1Defense Tech ×1Enterprise Software ×1Fintech ×1
HQs:United States×6Canada×1
Investments · 16 tracked
founders shown can be your intro pathAirbase develops intelligence and data products for aerospace, defense, and related sectors, built by technical operators with backgrounds in satellite imaging, orbital missions, and deep tech.
Deep TechDefense TechGovTechSaaSSpace TechNew York, US
VirgilHR is a compliance platform built by HR professionals that helps teams navigate complex employment laws across all 50 states through attorney-informed guidance and intuitive workflows. The platform simplifies onboarding, policies, multistate requirements, and employee relations for HR teams seeking to reduce risk and save time.
HR TechLegalTechGaithersburg, US
Wyvern develops high-resolution hyperspectral imaging satellites and delivers satellite-based earth observation data for model-based predictions. The company operates a satellite constellation in the space technology and remote sensing sector.
Advanced ManufacturingAgTechClimate TechDeep TechSpace TechEdmonton, CA
Chris Robson(Founder)inKurtis Broda(Founder)inKristen Cote(Founder)inCallie Lissinna(Founder)in
Board seats · per SEC filings · 4
what is this? ⓘ$2.2M raise · filed Jun 2026 · via Guy B. T. Filippelli
$15.9M raise · filed Sep 2025 · via Guy W. Filippelli
$30M raise · filed Mar 2025 · via Guy M Filippelli
$10M raise · filed Jan 2025 · via Guy Filippelli
Inferred from directors named on each company's SEC Form D — public regulatory data, not a portfolio list published by the firm.
Frequently asked questions
- What stage does SQUADRA VENTURES invest at?
- SQUADRA VENTURES invests at the Pre-Seed, Seed, Series A, Growth stages.
- What sectors does SQUADRA VENTURES focus on?
- SQUADRA VENTURES focuses on Cybersecurity, Defense Tech, Sector Agnostic.
- Where is SQUADRA VENTURES located?
- SQUADRA VENTURES is headquartered in Baltimore, US.
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