HelloSky Announces $5.5 Million Oversubscribed Seed Round, Crosses $1 Million ARR and Expands Executive Team

April 23, 2025 – HelloSky (formerly Skyminyr), a talent intelligence platform purpose-built for the executive search industry, has closed a $5.5 million oversubscribed seed round. The raise includes participation from Caldwell Partners, Karmel Capital, True, Hunt Scanlon Ventures and prominent angel investors from Google and Cisco Systems.

“As competition for executive talent escalates, organizations will increasingly turn to recruiting partners leveraging AI-driven platforms to gain a strategic edge,” said Scott A. Scanlon, CEO and co-founder of Hunt Scanlon Ventures. “They will lean on recruiters who can tap into precision talent platforms like HelloSky to integrate candidate identification, behavioral analytics, sector mapping, and human capital intelligence all in one place,” he said. “For executive recruiters this means shorter cycle times, more mandates, and unprecedented growth opportunities.”

The proceeds of the funding will be invested primarily into engineering and go-to-market efforts.

HelloSky has surpassed $1 million in annual recurring revenue (ARR) and expanded its management team to add executives in sales and marketing. Hugh Burnham has joined the company as EVP, sales and marketing, and Mike Kelch has joined as vice president of sales. Mr. Burnham previously ran his own marketing and public relations agency serving B2B technology startups for the past 21 years prior to its acquisition in 2023. Mr. Kelch has extensive experience in go-to-market and customer growth strategies for AI-driven solutions from previous roles at Scandit, Leafly and GolfNow.

Purpose-Built for Executive Search

While many AI recruiting platforms have added executive search features as an afterthought, HelloSky was engineered from the ground up with AI and data science tailored specifically for high-stakes executive placements. The platform delivers unmatched precision in identifying candidates with exact-fit experience and qualifications for leadership roles.

HelloSky has built a proprietary data science flywheel over five years, continuously training its talent intelligence models on behavioral signals, query patterns, and placement outcomes from over 700 expert executive search users. This reinforcement loop enables the system to optimize for precision discovery in the most complex executive searches, including those traditionally considered unsearchable.

Unlike platforms designed for staff-level recruiting, HelloSky offers advanced executive competency smart tags, relationship intelligence and connection pathing, revealing actionable routes to top talent based on deep employment, investment, and education graphs, not just superficial LinkedIn ties.

A Unified Talent and Intelligence Ecosystem

HelloSky consolidates human capital, company, talent, and investor data into a single AI-powered platform, said Mr. Scanlon. “With dynamic market mapping, real-time tracking, and its newly launched SmartRank technology, HelloSky is a game-changer for how executive talent is sourced and evaluated, eliminating the need for multiple disparate costly subscriptions,” he added.

SmartRank transforms natural language job descriptions into structured qualification maps, then algorithmically identifies and ranks the most relevant candidates from HelloSky’s proprietary data platform—bringing unprecedented speed and precision to the talent discovery process, based on verified user reviews and market presence.

Related: Executive Search 2025: Balancing AI Innovation with a Human Touch

Other platform capabilities include investor intelligence to reduce reliance on tools like Pitchbook, and smart tags that assess factors such as revenue scale, recruitability, and network scoring to identify optimal connection paths to candidates.

Integration with the Most Popular ATS and TRM Platforms

HelloSky is integrated with the most popular applicant tracking systems (ATS) and talent relationship management systems (TRM). In order to foster a seamless recruiting workflow, thereby allowing access to candidate information, improving collaboration and providing a unified dashboard of all applicant data without switching between platforms.

The Evolution of Executive Recruiting in the Age of AI

Artificial Intelligence is revolutionizing executive search by enhancing the efficiency of research, candidate sourcing, and assessment processes. AI-powered tools analyze vast datasets to identify potential candidates, assess their qualifications, and predict how well someone might fit a role, according to article from global talent provider True’s Josh Withers. “Talent mapping, once a drawn-out process, is now faster thanks to real-time insights into market trends and candidate availability,” he said. “We’ve reached a point where AI isn’t in the distant future; it’s actively reshaping how we find top-tier talent today.”

HelloSky integrates with Ashby, Clockwork, Ezekia, Gem, Greenhouse, Invenias, Loxo, Salesforce, and Thrive. The platform also integrates with all assessment data to provide a more nuanced view into candidate qualifications.

Strong Early Adoption and Industry Recognition

Several of the fastest-growing executive search firms have already adopted HelloSky, including enterprise deployments at Bespoke Partners, Caldwell Partners, NU Advisory Partners, and ON Partners. Venture capital and private equity firms are also turning to HelloSky to power talent decisions across their portfolios.

“This is a watershed moment for executive search,” said Alex Bates, CEO of HelloSky. “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 was recently named to the High Performer Quadrant in G2’s ranking of top Talent Intelligence Software.

HelloSky expects to reach profitability by the fourth quarter of this year.

Book a demo with HelloSky today!

Contributed by Scott A. Scanlon, Editor-in-Chief and Dale M. Zupsansky, Executive Editor  – Hunt Scanlon Media