Underscore VC

We’re out of stealth! Today we’re launching Terra Security - the world’s first agentic AI pentesting platform, with a built-in human-in-the-loop mechanism. We’re excited to announce our $8M seed round from SYN Ventures, FXP, and Underscore VC. Grateful to be backed by some of the best minds in security and AI. Attack surfaces are growing faster than ever while GenAI is hyper - accelerating developer velocity, and adversaries are evolving just as fast - using dark LLMs to launch scalable, more sophisticated, semi-autonomous exploits. Traditional pentesting and security teams simply can’t keep up with the pace of change. We’re reimagining offensive security with a service-as-software approach - combining the creativity of elite ethical hackers with the scale and speed of AI agents. The result: continuous, context-aware, human-validated pentesting - not once a year, but every time your attack surface changes. Our dream team of security experts, AI builders and researchers is in full- speed mode, tackling one of the most challenging and exciting problems in cybersecurity. Huge thanks to our early design partners, customers, and investors. You believed in us before the world knew our name. Check us out: https://lnkd.in/deRdc_hZ Follow Terra Security - big things are coming soon. :) Link to the full announcement in the first comment. Tsahy Shapsa, Gil Zimmermann, Ron Zalkind, Jay Leek, Marcio Lempert, Art Coviello, Jr, Richard Dulude, Brian Devaney, Ryan Permeh, Ofer Ben-Noon, Ohad Bobrov, Gerhard Eschelbeck, Travis McPeak, Dan Benjamin, Daniel Krivelevich 🇮🇱, Amit Bar On, Ian Andrews, Yossi Matias, Michael Matias, Gev Hadari, Shay Nahari, Itamar Friedman, Eran Vaknin, Alon Boxiner, 

We’re out of stealth and proud to share our $8M Seed round! Penetration testing is broken. It’s slow, expensive, and practically impossible to scale. Meanwhile, attack surfaces are growing faster than ever and security teams can’t keep up with the pace of change, while adversaries are faster, better and more sophisticated than ever, powered by automation and dark LLMs. We kept asking ourselves: What if we could combine the creativity of the best ethical hackers with the scale and creativity of AI? That’s how Terra Security was born. Not another automation tool. Not a faster checklist. A swarm of AI agents trained to think and act like ethical hackers - exploring, adapting, reasoning, exploiting - in real time, at scale.  It’s Agentic AI - and it’s a whole new way to think about ethical hacking. But before there was a product, there were people. We started by bringing together a team we knew by heart: AI Engineers and security experts we’ve built with, learned from, and trusted through the toughest challenges. People who’ve been in the trenches. People who don’t just talk security - they live it. Together, we’re building something that can truly shift the industry. We’re blessed to be backed by the best: SYN Ventures, FXP and Underscore VC - who believed in this vision before it had a name, and pushed us to make it even bigger. More than anything, I couldn’t ask for a better partner on this journey than Gal Malachi 🕵️♂️ We’re just getting started.

We're thrilled to back Terra Security founders Shahar Peled and Gal Malachi, who bring the perfect blend of cybersecurity expertise and go-to-market experience to pioneer the first agentic, AI-native, web app penetration testing service. As AI-driven cyber threats outpace traditional security methods, Terra transforms penetration testing from periodic manual checks to continuous automated monitoring—identifying threats in real-time while converting a costly service into a scalable, high-margin software solution. Learn why we invested: https://lnkd.in/eV4zPn9b

Last night we hosted a great group of Boston Future Founders - product leaders, engineers, startup operators, researchers, and students — all exploring pressing unsolved problems and what it takes to hop into the entrepreneurial journey. It was an evening of sharp ideas, open conversations, and new connections — the kind of gathering that reminds us why we invest at the earliest stages, and why bringing communities of builders together can be magic. Thanks to everyone who joined us and to SVB for partnering with us. We’re excited to see where the ideas and this future founder community go from here.

Yvonne Hao, thank you for your service, your energy, your relentless commitment to "Team Massachusetts. " You've been a role model of private sector + public service leadership that we need more of in the world to tackle today's challenges. “Yvonne has been the Energizer Bunny for economic development, and really has been an incredible catalyst for some transformative approaches,” Healey said in an interview. “Nobody hustled more over the state than Yvonne.” https://lnkd.in/eY3u_dk4

We gathered a small group of Boston's repeat founders this week for dinner—thank you to everyone who joined and shared hard-earned wisdom from your first, eighth, or even twenty-fifth time building. At Underscore VC, we believe in the power of community—and this was a special one. Thoughtful, candid, and deeply insightful. A few takeaways that stuck with us from the night: ·     The shift from “prove out” to “roll out” fundamentally changes how you think about team, titles, and execution. ·     In the early days, focus on removing market friction first, business friction second. Timing matters. ·     As software become commoditized, where does enduring value come from? What skills do you need on your team (and as founders) to capture it? ·     Is it a “designer” -- those who can deeply understand and design for the problem? ·     Will the future of engineering look more like medicine – will we need more “specialists docs” versus “generalists”? ·     On the macro level – are we moving away from capitalism towards tribalism? What does this potential shift mean for entrepreneurs? Big thanks to Laura Stoffel from Gunderson Dettmer for partnering with us—and to this group for reminding us why we love building with founders, not just funding them.

Come July, we'll see you at TechCrunch All Stage in Boston! Chris Gardner will speak on the game-changing ways AI is turbocharging MVP development. He'll also share where some founders get it wrong by letting the robots do all the thinking. Where are you seeing AI boost MVP development?

Huge congrats to Jeremy Allaire and the team at Circle on today's IPO filing. This moment is an excellent reminder of what it really takes for a founder to take an Idea → IPO: 1️⃣ Relentless Execution + 2️⃣ Unwavering Vision + 3️⃣ Resilient Persistence. I am grateful to have seen Jeremey's example of what entrepreneurship looks like in action from its earliest days in downtown Boston, to its influence today on the future of finance. And equally inspired by the next generation of founders in the "Circle Mafia"—who are just embarking on their own adventures (we've already backed a few). Congratulations, Jeremy and team—here’s to the next chapter ahead! https://lnkd.in/eEF4MyM5

In this new AI landscape, where startups are achieving eye-popping ARR in mere months, what metrics truly matter? "The revenue itself is real and important. But it doesn't necessarily mean there's long-standing, enduring value being delivered in the same way ARR used to mean with enterprise SaaS," says our very own Lily Lyman in this Fortune piece. Growth speed is impressive, but staying power is everything. A must-read from Allie Garfinkle's Term Sheet Newsletter for anyone navigating the AI startup ecosystem or watching the revolution unfold! https://lnkd.in/eq_XQey7 What's your point of view? Share with us in the comments.

Underscore VC is seeking academic visionaries ready to leap into entrepreneurship. This program isn't just funding — it's your gateway into Boston's tech ecosystem backed by our community-driven venture model. Named after our late Co-founder John Pearce, it embodies his unwavering belief in early-stage builders brave enough to transform ideas into reality. Applications close March 31st. This summer could be where your B2B software breakthrough finds its footing! Apply here: https://lnkd.in/e78EDZ6r