Squadra Ventures
Technology Focus Areas (Top 3): Cyber; IOT; Autonomy; AI
Series: Seed, Series A
Locations: Washington, DC
Squadra Ventures: History and Overview
The Story Behind Squadra
Squadra Ventures started in 2019 when Guy Filippelli decided to become the investor he wished he'd had as a founder. After successfully building and selling his cybersecurity startup RedOwl Analytics to Raytheon/Forcepoint for $54 million in 2017, Filippelli saw a gap in the venture capital world. Too many VCs in the defense and cybersecurity space weren't adding real value beyond writing checks.
As a former Army intelligence officer turned tech entrepreneur, Filippelli understood the unique challenges of building startups at the intersection of technology and national security. He named the firm "Squadra" (Italian for "team") to reflect his belief that the best results come from a collaborative, team-of-teams approach.
The core philosophy is simple: be the kind of hands-on partner that helps founders navigate the "100 decisions" they'll face in their startup's early years. Rather than just providing capital, Squadra rolls up its sleeves and works alongside founders to build stronger companies.
Fund History and Growth
Fund I (2019): Squadra's first fund raised about $27 million and backed 11 startups with typical investments of $500K to $2 million each. This initial fund had a broader tech focus and served as proof of concept for Squadra's high-engagement investment model.
Fund II (2021-2023): Building on the success of their first fund, Squadra launched Fund II in 2021, initially targeting around $80 million. Despite challenging market conditions for fundraising, they ultimately secured $105 million in commitments with plans to close between $110-120 million total.
Fund II represents a more focused approach, concentrating specifically on cybersecurity and national security ("dual-use") startups. The fund typically backs 12-15 companies with check sizes ranging from $2-4 million for Seed to Series A rounds. Squadra often leads these rounds, coming in as the first institutional investor after angels or accelerators.
Overall, Squadra has raised approximately $132 million across both funds. They're headquartered in Baltimore with a second office in Washington, DC – positioning them perfectly between startup ecosystems and the national security community.
What Makes Squadra Different
Squadra focuses on early-stage cybersecurity and national security companies – what they call "dual-use" technology that serves both commercial and government markets. This isn't just about the sectors they invest in; it's about how they support their portfolio companies.
The Four-Point Support System: After investing, Squadra's team focuses on four key areas:
Getting the business fundamentals right
Sharpening the go-to-market strategy
Making transformational hires and customer/partner introductions
Driving relentless execution of the plan
Deep Network Effects: What sets Squadra apart is their extensive network of operating partners, venture partners, and preferred service providers. This isn't just about making introductions – it's about providing startups with experienced operators who can jump in and help solve specific challenges.
Squadra applies what they call a "growth-stage mindset at the seed stage." They're willing to invest in strong teams and compelling visions even before companies have government traction, then use their network and expertise to help those companies navigate complex sectors like defense contracting and federal sales.
The Team Behind the Investments
Guy Filippelli – Managing Partner: The founder brings a unique combination of military intelligence background (he's a West Point grad), successful entrepreneur experience (two exits including RedOwl), and deep understanding of the national security ecosystem. He also chairs a veterans nonprofit and sits on the National Cryptologic Foundation board.
Dan Madden – Principal (National Security): A former Marine Corps artillery officer who became a leading voice in defense tech. He previously ran the Mid-Atlantic region for the DoD's National Security Innovation Network (NSIN) and worked as a senior policy analyst at RAND Corporation. His Pentagon and Capitol Hill experience gives Squadra's portfolio companies insider knowledge on federal go-to-market strategy.
Margaret Roth (Falzon) – Principal & COO: A "recovering startup founder turned VC" who co-founded data analytics company Yet Analytics before joining Squadra. She runs post-investment support for dual-use and enterprise software companies and is known in the ecosystem as a "founder therapist" for her mentorship approach. She also writes regular advice columns for Technical.ly and speaks at industry events.
John Timken – CFO/COO: Brings over 13 years of VC and private equity experience from firms like Camden Partners. He handles the firm's finances, compliance, and fundraising while helping portfolio companies professionalize their financial operations.
The team also includes principals like Isaac Carp (deal sourcing), Meghan McGee (platform support), and Dom Ventimiglia (network operations – a retired Green Beret who builds military and government relationships). They work with various operating partners and advisors who provide specialized domain expertise.
Building Thought Leadership
Despite being relatively young, Squadra has built a strong reputation through media appearances, industry panels, and original content. The team regularly speaks at conferences and contributes insights to the broader startup community.
Guy Filippelli has been featured in publications like the National Security Innovation Network's investor spotlight series and gave an in-depth interview to Infinite Frontiers about investing at "the critical edge of national security." Margaret Roth writes regular founder advice columns and moderated panels at Johns Hopkins on startup team evaluation.
The firm also produces original content, including Guy's popular "5 Minute 5 Point Pitch" framework that outlines what investors look for: problem definition, market opportunity, differentiation, team strength, and execution plan.
Through these activities, Squadra positions itself not just as a funding source but as a thought leader helping to shape conversations around cybersecurity and defense tech investing.
Portfolio Wins and Impact Stories
Squadra's track record includes both successful exits and strong growth stories that validate their hands-on approach:
Early Exits: Fund I delivered early wins with Privva (cybersecurity vendor-risk platform) and Pinkaloo Technologies (fintech charitable giving tools) both being acquired in 2021. These exits proved the value of Squadra's intensive support model.
Shift5 – The First Investment Success: Squadra's very first investment was Shift5, which provides cybersecurity for operational technology in planes, trains, and military platforms. Guy Filippelli calls it "massively successful" – the company has grown from a startup with no DoD traction to securing major defense and commercial contracts including U.S. Air Force projects and transit system deals.
NetRise – Dual-Use Champion: This firmware and supply-chain security company exemplifies successful dual-use execution. Under Squadra's guidance, NetRise has landed significant enterprise customers and major government contracts with DHS, CISA, and the Department of Defense. It shows how Squadra's federal network helps companies navigate both commercial and government markets.
Instant Teams – Rapid Growth: This remote workforce platform (focused on military spouses and diverse talent) made the Inc. 5000 list of fastest-growing companies after Squadra's investment, demonstrating the firm's ability to identify and accelerate high-potential startups.
Primordial Labs – Cutting-Edge Defense AI: A newer Fund II investment building AI-driven natural language interfaces for warfighters to control drones and robotic systems. Nearly 100% defense-focused, it shows Squadra's willingness to back truly innovative defense-specific technologies.
The Secret Sauce
What makes these success stories possible is Squadra's philosophy of "expanding the capacity of portfolio companies while also providing funding." They don't just write checks – they become embedded partners in building the business.
This means helping refine business strategy, opening doors to customers and partners, making key hires, and providing ongoing operational support. For companies in complex sectors like defense, where founders might need help navigating policy hurdles or connecting with government buyers, this kind of support can make the difference between success and failure.
As Margaret Roth puts it, the firm's priority is providing transformational support that positions companies to win in their markets. It's this combination of capital, expertise, and network that allows a relatively young fund to punch above its weight in the competitive world of early-stage investing.
From Baltimore and DC, Squadra continues to identify and support the next generation of cybersecurity and defense technology companies, applying the same founder-operator mindset that drove Guy Filippelli's own entrepreneurial success to helping other entrepreneurs build category-defining businesses.
