The first version of Nick Cromydas’s career plan met the class of 2009 and lost in straight sets. He had finished four years of varsity tennis at Vanderbilt, captained the team twice, studied communication and managerial studies, and wanted to become a strategy consultant. There was one hitch: he had not followed the usual campus-recruiting route, and the economy was in no mood to forgive a missed appointment.
So Cromydas went back to the skill he already owned. He became a volunteer coach for Northwestern’s women’s tennis team, working long days on court while trying to find his way into business. He later joked that he had been a professional tennis player for a week. This is the sort of credential that rarely survives the first pass of a résumé parser, though it makes an excellent opening chapter.
Coaching did more than pay in experience. It gave him and Scott Kacyn, a Vanderbilt friend with a computer-science background, a problem worth building around. College athletes spend years acquiring discipline, a network and a peculiar ability to remain pleasant while exhausted. Then many reach graduation with only a foggy idea of what comes after sport. Cromydas and Kacyn built Athliance, a small platform meant to connect athletes with alumni who could talk about life and work.
The customer list was admirably concise: Northwestern and Vanderbilt. Each paid roughly $25 or $50 a month. Nobody was measuring annual recurring revenue in champagne. Yet the product did the important work of a first company. It made an idea visible, forced its builders to find users and gave Cromydas proof that he understood technology well enough to be useful. That proof helped the former tennis coach land a consulting role at KPMG.
A career built one connection at a time
The summer of five yeses
After consulting came New Coast Ventures, the Chicago venture studio Cromydas founded with Kacyn. It built products, advised companies and made early-stage investments. The firm would eventually start or back more than 40 companies. It also provided the vantage point for a more durable idea.
Around the summer of 2014, an executive-recruiter friend began asking Cromydas for help with digital roles. He would scan Cromydas’s LinkedIn network and ask for introductions to people who might fit. Cromydas obliged. Over four or five months, five people were placed. Then the candidates wrote back with some version of the same message: they had taken the conversation seriously because it came through him.
“Trust is what powers someone listening to an opportunity.”Nick Cromydas
The candidate had not become reachable merely because a database contained a name. The introduction carried context. It borrowed credibility from an existing relationship. For a happily employed executive, that difference can separate an interesting interruption from one more message beginning with an extravagant compliment about a profile.
Cromydas spent weeks observing large executive-search firms. He saw experienced recruiters research markets, work their own relationships and ask those contacts for more names. The craft was human and often impressive. The machinery beneath it was surprisingly slight. Valuable knowledge lived inside individual address books and memories. When a recruiter left, much of that private map could leave too.
Hunt Club grew from the question hiding in those observations: what if a search firm could give every recruiter access to a much wider field of trusted connections, then use software to make the field navigable?
A Rolodex with a memory
Hunt Club launched from closed beta in 2015. Its model paired a recruiting service with technology and a network of business leaders who could make warm introductions. Rather than deliver an enormous candidate list to a client, the system searched for likely fits, found credible routes into their networks and narrowed the field through screening. The client received a small set of serious candidates, not a digital haystack accompanied by best wishes.
The approach had an elegant loop. Many experts in Hunt Club’s referral network were hiring managers themselves. A good introduction could produce a candidate, then a customer. Candidates who enjoyed the process could return later with roles of their own. The network did not merely expand; it circulated.
By December 2022, the company said it had placed more than 1,000 leaders, built a community of 20,000 business leaders and mapped access to more than seven million candidates. It reported that revenue had grown 156 percent from the prior year. Hunt Club then raised a $40 million Series B co-led by WestCap and Sator Grove, following a $10 million Series A the year before.
Those figures belong to a particular moment in a cyclical industry, but they show the scale of the bet. Cromydas was not selling a clever referral widget. Hunt Club remained a full-service search firm, with recruiters who learned the role, managed the process and interpreted what the software surfaced. Technology automated research, profile enrichment, communications and scheduling. People handled the parts where ambiguity is not an error state.
The point after the bad point
Company stories grow tidier in fundraising announcements. Hunt Club’s was not. In 2020, the pandemic helped kill an acquisition deal and revenue fell 80 percent, Cromydas later recalled. Leadership compensation was cut. Costs came down. The team searched for industries and roles where demand remained, and within months the company was exceeding its goals again.
Cromydas describes resilience as a matter of recovery speed: the problems do not become less real, but the time needed to return to useful action gets shorter. It is difficult not to hear a tennis player in that definition. During his junior year at Vanderbilt, he opened dual play 2-7, then finished the season 9-4. The lost point is gone. The next one requires a serve.
That competitive streak sits beside a conspicuous preference for openness. On a 2024 podcast, he discussed Hunt Club’s monthly all-hands meeting as a place designed for direct questions and shared context. His argument was practical: people cannot close the gap between a company’s plans and reality if they are uncomfortable admitting what they do not understand.
“If you don’t really build a culture where people are comfortable asking a really hard or direct question, it’s impossible to actually close the gap.”Nick Cromydas
Former teammates and colleagues describe a leader who listens, relates easily to people and competes hard without requiring the room to orbit him. Those are flattering accounts, naturally, but they are also consistent with the company he chose to build. Executive search is commercial matchmaking conducted under deadline. Curiosity and listening are not decorative virtues there. They are production tools.
What AI cannot introduce
Cromydas’s recent writing turns from recruiting technology to AI-native services. He argues that older search firms cannot sprinkle artificial intelligence onto isolated books of business and expect the knowledge to compound. Interviews must become structured insight. Warm introductions must be tracked. Relationship data must serve the firm rather than vanish inside a rainmaker’s private system.
His complaint is less about old technology than old incentives. Traditional firms often reward individual production, leaving small teams to guard relationships even while sharing a company name. In that arrangement, one recruiter may know exactly when a candidate changed jobs, when a client raised capital or when a former colleague became the ideal bridge between them. The firm itself learns almost nothing. Cromydas wants the system to notice those signals, prompt the useful follow-up and preserve what each search teaches. It is a practical notion of institutional intelligence: fewer heroic feats of memory, more chances for good judgment to travel.
At the same time, he resists the convenient fantasy that software can perform the whole search. A senior hire is a sequence of judgments about competence, appetite, timing, chemistry and risk. AI can flag a funding event, surface a connection, enrich a profile or draft a follow-up. It cannot retroactively manufacture the history that makes an introduction trusted. The machine can remember the door. Someone still has to be welcome when it opens.
In 2026, Cromydas was publicly noticing executives making unconventional moves: chief technology officers becoming staff engineers, chief executives taking business-development posts, and other senior people choosing proximity to the work over the tidy ascent of titles. He found the pattern encouraging. It fits a career that began with a missed corporate entrance, detoured through a tennis court and discovered its central idea in the favor one friend does for another.
Hunt Club’s ambition is now larger than those first five introductions, but the original mechanism remains legible. Find the right person. Discover who can speak credibly to them. Give both sides enough context to take one another seriously. The software may become smarter; the databases may become larger. The decisive moment is still wonderfully old-fashioned: someone you trust says, “You should take this call.”