HelloSky Uses AI to Simplify Executive Talent Search

Filling executive roles can feel like searching for a needle in a haystack. HelloSky is reimagining how top-tier talent gets discovered.

It is the only talent intelligence platform purpose-built for the executive search industry.

HelloSky distinguishes itself from many AI recruiting platforms by being specifically designed for executive search, rather than adding it as a secondary feature. Leveraging AI and data science from its inception, HelloSky offers superior precision in matching candidates with the precise experience and qualifications required for critical leadership positions.

In a Business Insider interview, the CEO and co-founder of HelloSky, Alex Bates, stated that their approach to talent acquisition differs from most companies that prioritize staff recruiting. The company focuses on advanced executive competency smart tags, relationship intelligence, and connection pathing. This allows them to uncover actionable pathways to top talent by leveraging comprehensive employment, investment, and education data, going beyond surface-level connections found on platforms like LinkedIn.

Executive hiring is one of the toughest challenges companies face. The best candidates are rarely on the market, timelines are long, and the stakes are high and a bad hire can derail strategy and culture. Traditional search methods rely heavily on networks and gut instinct, often leading to bias and missed opportunities. Meanwhile, competition for top talent is fierce, and global hiring adds layers of complexity. In this high-stakes, fast-moving landscape, companies need smarter, faster, and more transparent ways to find the right leaders.

Harnessing the power of AI, Hellosky reshapes executive hiring into a dynamic, data-driven process. Its platform doesn’t just scan resumes—it reads between the lines. By analyzing patterns in leadership trajectories, company performance, cultural signals, and industry shifts, Hellosky surfaces high-impact executives who may not even be on the market yet, but are the perfect fit.

The system goes beyond matching titles or keywords. It evaluates potential based on outcomes, not just experience, and identifies leaders with the proven ability to drive results. Outreach and qualification are intelligently automated, cutting down the time to hire while maintaining a high bar for quality. What used to take months can now take weeks.

This one of a kind company has just announced a successful close of a $5.5 million oversubscribed seed round, which includes participation from Caldwell Partners, Karmel Capital, True, Hunt Scanlon Ventures and prominent angel investors from Google and Cisco Systems. The proceeds of the funding will be invested primarily into engineering and go-to-market efforts.

“This is a watershed moment for executive search,” said Bates. He added “AI is no longer a futuristic concept, it’s a competitive advantage today. Firms that embrace our platform are the fastest growing firms in executive search, achieving better outcomes with higher candidate precision and placement success.”

HelloSky has achieved an Annual Recurring Revenue (ARR) exceeding $1 million. Additionally, the company has strengthened its leadership by appointing new executives in sales and marketing.