Let’s talk about a company that isn’t just sky-high on ambition, they’re HelloSky, and they’re putting the “intel” in intelligence when it comes to talent. Founded in 2020 by Alex Bates, this San Diego-based crew isn’t just playing in the executive search game, they built the court. Their $5.5M seed round, closed April 23, 2025, was oversubscribed. You know you’ve struck a nerve when investors like Caldwel Partners, Karmel Capital, True Capital Partners, and Hunt Scanlon Ventures want more than a seat, they want a stake. Sprinkle in angels from Google and Cisco, and you’ve got yourself a power move.
HelloSky (formerly Skyminyr) doesn’t mess with off-the-shelf. They tore down the old model and rebuilt it from ground zero for one purpose: make executive search smarter, faster, and dead-on accurate. In an industry where others retrofit AI like patchwork on a leaky pipe, HelloSky designed their platform from the DNA up, trained on five years of behavioral signals, search outcomes, and more than 700 search pros’ real-world moves. This isn’t LinkedIn in a tuxedo, it’s precision-targeted, deep data, relationship-mapped intelligence. Superficial ties? Leave that to your cousin’s MLM pitch.
Now, $1M in ARR might not buy you a seat at the big boys’ table, but hitting that mark with enterprise clients like Bespoke Partners, Caldwell, Eastward, NU Advisory Partners, and ON Partners? That’s more than noise, it’s momentum. Their AI promises 80% faster talent acquisition, 10x better candidate quality, and double the retention rates. Not hype, outcomes. And they’re not stopping. With SmartRank™ converting human-speak into talent gold, and Relationship Intelligence finding paths to top execs you won’t catch on public feeds, this team’s gunning for profitability by Q4.
Alex Bates, CEO, tech veteran, and author of “Augmented Mind,” leads this charge, backed by EVP of Sales Hugh Burnham and VP Mike Kelch. They’re scaling not just tech, but talent, fueling growth with a tight crew and sharper execution. And let’s be clear, this isn’t just tech for tech’s sake. As Hunt Scanlon Ventures’s Scott A. Scanlon says, AI’s now the edge in exec search. Bates? He calls it a watershed moment. Me? I say they’ve seen the storm coming and built the damn dam.
Let’s connect and keep the momentum going across the tech ecosystem. Whether you’re a founder shaping the future, a leader driving change, a VC backing bold ideas, or an investor spotting the next big thing—together, we’re pushing boundaries. Proud to be building the future with you.
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