Before he was helping companies protect themselves from hackers, Hector Monsegur was one. Operating under the alias “Sabu,” Monsegur was one of the most notorious members of the hacker collective Anonymous in the early 2000s, responsible for high-profile intrusions into government and corporate systems worldwide.
Today, he’s turned that experience into a force for good as a cofounder of SafeHill, a cybersecurity startup that just came out of stealth with $2.6 million in pre-seed funding.
SafeHill aims to combine the precision of AI with the intuition of human ethical hackers to help companies spot and fix vulnerabilities before attackers can exploit them. Its flagship platform, SafeHill SecureIQ, runs continuous penetration testing – what insiders call “Threat Exposure Management” – so organizations can stay one step ahead of evolving cyber threats.
“Cyber threats are evolving faster than ever, overwhelming security teams with alerts and noise,” said CEO Mike Pena in a statement. “Our platform combines AI-driven continuous penetration testing with expert human validation to cut through the noise, focus on real risks, and deliver the impact of a dedicated team of ethical hackers at scale.”
While SafeHill has its headquarters in Chicago, the company’s story has deep roots in Miami. Patrick Cohen, a Miami native and one of SafeHill’s senior advisors and early investors, told Refresh Miami that his involvement started when Monsegur – whom he first met more than a decade ago – called to share what he and his cofounders had built during Techstars Chicago.
“He told me, ‘We built a software that does automated penetration testing,’” Cohen said. “He’d finished the program at the top of his class and wanted some help connecting with investors and customers. So I came on as an advisor and investor, and brought in a network of venture capital contacts, practitioners, and clients, some from right here in South Florida.”
Among those connections were Ted Lucas and Hilmon Sorey of The Source Group, who also joined the round, along with Mucker Capital and Chingona Ventures, a Latina-led fund out of Chicago. That mix of backers helped SafeHill expand its reach quickly.
Cohen’s own career has spanned Wall Street, real estate, and workforce development. He previously helped lead the tech training nonprofit NPower, which incidentally counted Monsegur among its early students after his release from prison.
“He’s one of the nicest guys you’ll meet,” Cohen said. “He’s a self-taught genius who’s now using that same knowledge to help protect people instead of hacking them.”
That mix of redemption, community, and innovation runs throughout SafeHill’s work. Cohen helped organize a hackathon at Miami Dade College, bringing together students from FIU, Florida Memorial, and local high schools to compete in a “capture the flag” cybersecurity challenge. “The winner was a Cuban immigrant,” Cohen said. “SafeHill ended up hiring him. It was a full-circle story.”
The team has also kept a local presence: cofounder Nicholas Gonzalez, a former FIU baseball player, now lives in Miami, which serves as a satellite office. “Miami’s a key part of the story,” Cohen noted.
SafeHill’s early customers include small and mid-sized academic institutions including many historically Black colleges and universities (HBCUs) that have faced major cyberattacks in recent years. But the goal, Cohen said, is to scale into enterprise-level clients across finance, healthcare, and government.
“The future is going to be automated pen testing,” he added. “That’s where the industry is headed, and SafeHill is one of the first in the market doing it right, with a celebrity hacker behind it and a strong ethical foundation.”
Pictured at the top of the post: Mike Pena, Nicholas Gonzalez, and Hector Monsegur.
READ MORE IN REFRESH MIAMI:
- From bartender to MasterCard: Toni Yates’ cybersecurity career journey with help from Miami Dade College
- From hacker to investigator, this cybersecurity expert built a business by thinking like a criminal
- Guardz raises $56M to arm MSPs with enterprise-grade cybersecurity for the SMB economy
- Pillar Security raises $9M to create AI security guardrails for enterprises
