HelloSky raised $5.5 million to use AI for recruiting hard-to-reach executives. Check out its pitch deck.
HelloSky, a startup that has built a platform to help recruiters find executives with AI, just raised a $5.5 million seed round.
While many hiring platforms focus on staff-level roles, HelloSky was built specifically for high-stakes, complex leadership searches.
"Most companies go after staff recruiting first and tack on exec search later," HelloSky's founder and CEO, Alex Bates, told Business Insider.
Executive hiring comes with a different set of challenges, according to Bates. These roles, he says, are often confidential and have hard-to-reach criteria, like sector experience, international exposure, past exits, and team fit.
Bates said recruiters still rely on LinkedIn, spreadsheets, or memory to find candidates. "It's a system set up to miss the best people — some of whom don't have a LinkedIn."
HelloSky helps recruiters and search firms identify and evaluate executive talent whose backgrounds closely match the role — even when they're hard to find through traditional methods.
Its "SmartRank" technology converts natural-language job descriptions into key skills and criteria, and then identifies and ranks the most relevant candidates from HelloSky's proprietary data platform.
HelloSky says its system has been trained on five years of data from more than 700 expert executive search users, based on how they search, sort, and select candidates.
"We kind of spent five years in the wild," said Bates. "It was a lot of heavy data engineering and experimentation with recruiters from day one." The startup says it continuously refines its models based on user behavior, query patterns, and placement outcomes.
The platform also maps real-world relationships such as shared board seats or leadership experience, rather than just "superficial LinkedIn ties," Bates said.
The platform runs on a subscription model, with customers ranging from corporate hiring teams to retained search firms. Clients include search firms like Caldwell, Eastward Partners, NU Advisory, and Bespoke Partners, who recruit executives for private equity-backed companies.
Investors in the oversubscribed round include Caldwell Partners, Karmel Capital, True Capital Partners, Hunt Scanlon Ventures, and angel investors from Google and Cisco.
The startup plans to use the new funding to scale its engineering and invest in go-to-market.
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