Squadra Blog

Navigating the AI Fog of War

harrison@squadra.vc (Harrison Lane) — Thu, 11 Sep 2025 16:34:09 GMT

The Pursuit Toward Higher-Stakes Military AI Deployment and Its Commercial Impact Beyond the Battlefield

No serious investor or technologist expects the next benchmark-breaking AI model to emerge from the Pentagon. With startups and tech giants releasing groundbreaking AI models every month, the march toward higher-performing AI lies squarely in the private sector. Benchmark-breaking models will keep coming from industry; however, the next step-change in value will come from proving reliability under real-world pressure, with defense as the hardest test bed.

The New Front Lines: How CUAS is Redefining Superiority in an Invisible Battlespace

camille@squadra.vc (Camille Scheyer) — Tue, 17 Jun 2025 16:23:55 GMT

In a battlespace that is increasingly decentralized, fragmented, and unpredictable, drones are not only growing in number, but rewriting the rules of engagement. Russia’s invasion of Ukraine is an unfortunate pinnacle example — Ukraine expects the manufacturing capacity of first-person-view (FPV) drones to triple this year to 4.5 million, and sell out of stock. These $300 (or cheaper) drones are accounting for 80% of casualties in Russia and Ukraine, and are destroying billions of dollars of weapons stockpile as Ukraine and Israel have most recently shown through discrete attacks.

Private equity veteran Meghan McGee joins Squadra as Head of Platform, reinforcing commitment to VC with growth-stage mindset

margaret@squadra.vc (Margaret Roth) — Tue, 20 May 2025 12:14:55 GMT

FOR IMMEDIATE RELEASE

BALTIMORE, MD — MAY 20, 2025 — Squadra Ventures, a venture capital firm that invests in early-stage cyber and national security companies, announced today that Meghan McGee joined the team as Head of Platform. In this cross-functional role, McGee will deliver her expertise from deal-structuring to fundraising to exit across the Squadra portfolio.

McGee has spent the last two decades of her career in private equity at Camden Partners, leading full-spectrum, full-lifecycle strategic and operational support for lower middle market companies in enterprise software, business services, technology services, and FinTech. In her roles, McGee drove initiatives that accelerated the capacity building of great teams, backed them with the right resourcing, and fueled them through the growth stage.

“For founders, we have become tremendously known in the industry for providing access to a deep network and powerful acceleration through value-add post-investment initiatives,” said Guy Filippelli, Managing Partner. “We could not be more excited for Meghan to round out that support from pre-investment to post-investment. At Squadra, we are a team of teams, and now are maturing our strengths with full-lifecycle, full-stack support as a firm.”

Serving as board member, CEO thought partner, and strategic innovator, McGee provided invaluable support to dozens of companies across many stages of their journey. From investment to exit, McGee has worked with management teams to engage clients, secure partners, resource for acceleration, access the right talent and tools they need to thrive, and when the time was right, secure financing or exit.

A two-time graduate of the University of Maryland, holding her B.S. in Family Studies and her M.B.A. from the Robert H. Smith School of Business, McGee knows both sides of the equation for the company and for the buyer.

“I’ve looked at and worked with a lot of companies both as they seek their Series B and just after they have raised growth capital,” said McGee. “Taking them through the preparation towards that inflection point and helping them actually deliver on growth, I’m excited to build upon Squadra’s competitive advantage as a firm and for where these companies are headed next.”

Building on a strong seed-stage track record, it is this unique perspective and mindset of extreme preparation for the growth stage that McGee will aim to institutionalize at Squadra.

Deploying capital out of its second fund, Squadra has opened office operations at its flagship location in Washington, D.C. Located in the heart of downtown at Metro Center, the Squadra team is able to readily support portfolio company teams in their efforts with and across the federal government and United States Department of Defense, providing a home base steps from the Capitol and a short Metro-ride to the Pentagon.

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About Squadra Ventures

Press Contact: Margaret Roth <margaret@squadra.vc>

Squadra Ventures is a venture capital firm led by founder-operators that invests in early stage cyber and national security companies. Grounded in the belief that success is a combination of people, product, and planning, the Squadra team provides transformational support to startup leaders in the complex dual-use technology ecosystem. By applying a growth-stage mindset at the seed stage and a commitment to building alongside entrepreneurs, Squadra empowers extraordinary teams to win and leave a lasting positive impact on the world.

Learn more at https://squadra.vc.

Phin Security secures funding to build out Security Awareness Training, limiting risk of breaches and making cybercrime less profitable

margaret@squadra.vc (Margaret Roth) — Fri, 18 Apr 2025 18:45:33 GMT

WILMINGTON, DELAWARE – Phin Security, a company dedicated to transforming security awareness training (SAT) and phishing simulations, especially for managed service providers (MSPs), has secured seed funding from leading institutions, including Squadra Ventures, Mantis, Inner Loop Capital, and Mercato Partners as well as renowned cybersecurity experts such as those behind Perch Security, Empath, and Rewst.

Wyvern secures $6M to expand global footprint, bolster U.S. market presence

margaret@squadra.vc (Margaret Roth) — Tue, 22 Oct 2024 19:24:24 GMT

Wyvern Inc., a leader in commercial hyperspectral data with multiple operational in-space assets, today announced it has raised USD$6 million in a strategic investment led by Squadra Ventures . The round included follow-on investment from Uncork Capital and Y Combinator, and new investment from the University of Alberta Innovation Fund, Accelerate Fund III, and Brent Perrot. This funding marks a major milestone for Wyvern, enabling deeper penetration into the U.S. market while strengthening its position as a global leader in Earth observation.

The 239 interview questions technical startup founders should ask every candidate

margaret@squadra.vc (Margaret Roth) — Tue, 18 Jun 2024 15:16:33 GMT

There are few things as exciting as meeting with amazing new people who might be the right one to join your team. You found some great candidates, now how do you figure out if they are the one?

Real Talk: Cyber Markets and Seed-Stage Startups in 2024

adam@squadra.vc (Adam Bixler) — Mon, 29 Apr 2024 22:03:42 GMT

There are plenty of market assessments showing venture funding totals in cybersecurity startups have retreated from their recent highs. These macro perspectives show that investing in the space peaked in late 2021-early 2022, a time when work from home drove changes in enterprise security architectures, and CISO budgets appeared to be uncapped. Understanding the macro environment, and how it’s changed over time specific to cybersecurity, can help startups chart a path forward.

Squadra Ventures to Host Event Series at RSAC on May 7, Featuring National Cyber Director Harry Coker and Innovative Startups

stephen@squadra.vc (Stephen Babcock) — Tue, 23 Apr 2024 18:54:14 GMT

FOR IMMEDIATE RELEASE

BALTIMORE, MD, April 23, 2024 — Squadra Ventures, a venture capital firm that invests in early-stage cyber and national security companies, will host a daylong event series at RSA Conference, a premier cybersecurity industry event held annually in San Francisco.

Squadra Hub @ RSAC will serve as a showcase for the firm’s portfolio companies and a forum for cybersecurity leaders to share ideas and build relationships. The day will open with a breakfast keynote featuring National Cyber Director Harry Coker, Jr.

From 8:00 AM to 8:00 PM on Tuesday, May 7, Squadra Hub @ RSAC will gather innovation leaders from startups, industry, and government at Oren’s Hummus (71 3rd St., San Francisco). Located one block from the RSA Conference at the Moscone Center, this will offer a central connection point, off the conference floor, to have a meeting, network, and learn.

An AI MVP in the DoD

stephen@squadra.vc (Stephen Babcock) — Mon, 26 Feb 2024 17:48:52 GMT

When it comes to AI for warfighters, the DoD has a new MVP.

5 Ways a Small Team Can Make a Big Impact

stephen@squadra.vc (Stephen Babcock) — Fri, 23 Feb 2024 22:26:38 GMT

Hang out with people who have the same job as you. You’ll find that often you are going through the same challenges, and there are plenty of opportunities to learn from each other’s experiences. Community can be especially powerful if you are the only one at your company who does your job every day.