Squadra Ventures

Squadra Ventures is an early-stage venture capital firm founded in 2019 by Guy Filippelli, a former Army intelligence officer and founder of RedOwl Analytics, headquartered in Baltimore, Maryland with an office in Washington, D.C. The firm invests $1–4 million in pre-seed to Series A companies developing dual-use technologies for national security and cybersecurity, with a thesis centered on innovations serving both government and commercial sectors. Its portfolio includes 33 companies such as NetRise (firmware security for XIoT devices), Primordial Labs (AI for warfighter-system interaction), and Datalogz (BI operations platform), with notable recent investments in NetRise, Primordial Labs, and Datalogz from its $105 million Fund II closed in March 2023. Leadership includes Guy Filippelli (Founder & Managing Partner), Dan Madden (leads National Security practice), and Margaret Roth (runs post-investment support), supported by a network of 50+ venture partners. The firm operates with 11–50 employees, provides transformational post-investment operational support including go-to-market strategy and talent sourcing, and has made nine investments from its initial $27 million Fund I, including Overwatch Imaging and Instant Teams, with two portfolio companies (Privva and Pinkaloo) acquired. Squadra Ventures targets 1–2 investments per quarter, emphasizes a growth-stage mindset at the seed stage, and focuses on sectors including cybersecurity, defense, AI, healthcare, fintech, biotech, energy, IoT, proptech, and web3.