Prior Loudoun award winnner CalypsoAI raised $23M in a new Series A-1 round

An AI security company with connections to Northern Virginia just raised a whopping eight-figure sum.

The company is CalypsoAI, and the Series A-1 it raised tallied $23 million. The round was led by Paladin Capital Group. Existing investor Lockheed Martin Ventures also took part in the round, alongside new investors Hakluyt Capital, Expeditions Fund, Auren Hoffman and Anne and Susan Wojcicki. The company has a presence in California and Ireland, but boasts some senior leadership (including sales VP Jeff Howard) in Northern Virginia. According to its website, it also works with several government agencies that are headquartered in the DC metro area, where it also claims to be based on LinkedIn.

CalysoAI helps enterprise and government entities trust and monitor AI and machine learning. The company’s products test, validate and monitor AI applications, both internal and external before they’re deployed to make sure that they’re secure and deliver the outcomes they set out to do. With the funds, the company will build out its large language model security solutions, add talent and invest in go-t0-market strategies.

In 2020, the company raised $13 million in a Series A round also led by Paladin, and in 2019 the company raised $2.2 million in a seed round, according to Crunchbase data. In total, the company has raised $38.2 million since its founding in 2018.

According to CalypsoAI, many companies set written guidelines or ban large language models to mitigate risk, which its leadership feels isn’t the most effective approach. In fact, Neil Serebryany, founder and CEO of CalypsoAI, said that it can put companies behind others who are implementing technology.

“By adopting CalypsoAI’s solutions, every enterprise or government organization should be able to enable the benefits AI solutions deliver while having confidence that they are trusted, resilient and secure,” said Serebryany in a statement. “With support from some of the top investors and a drive to put LLMs in every worker’s hands, CalypsoAI is bringing the AI and cybersecurity markets together in a way that’s never been done before.”

So far, CalypsoAI has been recognized as a 2022 Gartner Cool Vendor for AI Core Technologies — Scaling AI in Enterprise and a top AI security solution provider by Forrester. Locally, the company was also named the grand prize winner of the Loudoun Economic Development Innovation Challenge.

“AISec technology will only become more critical to enterprises, and CalypsoAI has been leading the charge since the beginning,” said Mourad Yesayan, managing director at Paladin Capital Group. “The company’s unique mix of cybersecurity and AI talent, combined with its battle-tested technology, makes it a clear driver of the AI revolution. Paladin is proud to have been an early supporter of Neil and the team at CalypsoAI, and we’re excited to be leveling up our investment and partnership as the company accelerates the trusted adoption of artificial intelligence.”