Josh Lospinoso
Baltimore venture firms Squadra and Savano Capital Partners have joined a $75 million Series C funding round for Arlington, Va.-based Shift5, which is building an operational intelligence platform to enhance the security of the country’s defense and transportation systems.
The round was led by London-based Hedosophia, with participation from New York’s Insight Partners, Center 15 Capital, 645 Ventures, Moore Strategic Ventures, Booz Allen Ventures, AE Industrial, Disruptive and CSP Equity Partners.
Red Owl Analytics CEO Guy Filippelli launched Squadra after Raytheon acquired his cybersecurity and compliance firm for $54 million in 2017. Squadra’s investment is not regionally bound, but Baltimore is “our hometown, our headquarters, and our community,” Filippelli once said. The firm secured about $105 million for its second fund, raised in 2023.
The firm’s second fund focuses on cybersecurity and defense startups. It expects to back about 15 startups. Squadra used its first fund, worth $27 million, to back a broader range of startups.
Savano, founded by managing partner Tom Smith, primarily invests in tech startups. It has raised three funds, the most recent one closing at $157 million. Savano’s portfolio companies include WordPress parent Automattic, Upwork and Zeta Global. Smith, a former Chase Manhattan banker, has spent over three decades in venture investing.
Shift5 is led by co-founder and CEO Josh Lospinoso, a Rhodes scholar with a PhD in statistics. Lospinoso earned a BS (Honors) in Economics and Operations Research from the U.S. Military Academy at West Point. The company’s other co-founders are Michael Weigand and James Correnti. Both served the U.S. Army as cyber officers. Weigand has also served as an entrepreneur-in-residence at Squadra Ventures.
“When we started this company, we set out to solve some of the toughest challenges in operational technology for the nation’s critical systems, and this round marks a major milestone that validates our team’s work,” said Lospinoso. “More importantly, it provides rocket fuel to accelerate our mission of equipping the teams that operate and secure these systems with the infrastructure and analytics to detect threats, anticipate failures, and respond with confidence.”
The startup said the Series C round would help scale Shift5’s operational technology (OT) across defense and commercial transportation sectors as organizations face increasing cybersecurity threats and aging infrastructure challenges that demand real-time visibility into critical systems.
“Shift5 represents the kind of innovation we look for — a deeply mission-oriented team that’s built a uniquely capable platform,” said Richard Wells, Insight Partners’ managing director. “From our Series A investment through leading their Series B and now participating in Series C, we’ve seen them execute on transforming data into actionable insights. We’re excited to continue our partnership as they scale this technology across the critical systems that the defense and commercial communities rely on.”
Since its previous funding round, Shift5 has secured major defense contracts and secured strategic partnerships with Boeing, Avionica, ForeFlight, Booz Allen Hamilton, Carahsoft Technology Corp. and Amazon Web Services.
