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AI Squared: Building cutting-edge tech into software


AI Squared team1[1]
Benjamin Harvey, seated at center, with the AI Squared team.
Wale Ariztos Photography

Editor’s note: At the start of the year, we look at which young companies have caught our eye for hitting a milestone, bringing in funding or growing its revenue base. This company has made our list of our Startups to Watch for 2023. See them all here.


AI Squared founder and CEO Benjamin Harvey was inspired by a decade’s worth of work in the U.S. National Security Agency, working as a cryptologic computer scientist and, toward the end of his tenure, head of data science during the Edward Snowden leaks.

While at the agency, he created machine algorithms to help group files based on which subject matter experts had the best opportunity to analyze those files. In doing so, he realized an organization’s biggest challenge was repurposing or integrating an algorithm that took so much labor to build into a new application. In that problem, he saw an opportunity.

“How do you really make it useful? How do you increase that experience? How do you provide someone with something that actually makes sense for them to use?” he asked. “That’s the last-mile piece that we’re hoping to sell.”

AI Squared works like a Windows Installer Wizard, but for artificial intelligence algorithms, machine learning or predictive software for a company — essentially helping fit an AI algorithm’s square peg into a company’s existing software or platform’s round hole. The example Harvey likes to use is Netflix. Imagine that the video streaming giant wanted to use a new algorithm that predicted users’ movie tastes based off of their music tastes. AI Squared’s software helps ensure Netflix’s streaming technology plays nice with the algorithm, that the former doesn’t crash or the latter doesn’t spit out the wrong selections (i.e. you’re a fan of Marilyn Manson, but it’s suggesting the Hallmark Channel’s “Christmas Inheritance”).

Last summer, AI Squared closed a $6 million seed round led by VC bigwigs New Enterprise Associates, with participation from Ridgeline Partners. This year, the 2022 Inno on Fire honoree has plans to go even bigger and raise an ambitious Series A sum, between $30 million and $50 million.

Harvey’s pitch points to huge sales potential for the company, including $325 million in federal contracting opportunities. Its current client list includes Johns Hopkins University Applied Physics Lab, the Air Force and Department of Defense, with another 21 private sector companies still on a waitlist to use its technology once it can gather more resources to meet that demand. Ultimately, Harvey said, expect his company to become one of the region’s next unicorns, sporting that coveted billion-dollar-plus valuation.

“We do view ourselves as one of the top 1% of companies that are out there,” he said. “But at the same time, we have to have valuation discipline, where we don’t want to raise too much because we have to show investors we can also grow into our valuation as well.”


The basics

  • Location: D.C.
  • Founded: 2019
  • Leadership: Benjamin Harvey, CEO and founder
  • What it does: Makes it easy to integrate artificial intelligence- and machine learning-based algorithms into existing web-based applications
  • Employees: 20
  • Revenue: More than $1 million in 2022

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