How Chicago Is Winning The Hunt For Top Talent


With the flood of capital flowing into Chicago’s hot start-ups, founders are faced with new challenges, and the most pressing may well be talent recruitment. How do these start-ups attract the talent they need to help their businesses succeed? 

Chicago’s response to this changing market offers other cities a model for the way forward. While Chicago businesses are experiencing challenges in recruiting new talent, the city is also rising to the challenge with impressive new solutions. For example, I detailed why Chicago may be the best city to find a tech job thanks to the growth of new tech start-ups, citywide initiatives to attract talent to the area, and the influx of skilled tech talent over the course of the past two years in particular. 

More recently, Chicago-based recruiting firm Hunt Club’s $10-million funding round from Teamworthy Ventures demonstrates that Chicago is in the driver’s seat, not only in fostering a new age of talent innovation in Chicago, but also in offering scalable recruitment solutions for companies from coast to coast. And boy, does everyone need it.

We’ve seen more capital invested than ever before. The effects are clear. In 2020, 165 companies worldwide reached a valuation of $1 billion; in the first three quarters of 2021, we’ve already seen 403 new unicorns globally. 

Chicago’s local ecosystem has mirrored national and global trends. According to data from PitchBook, the Windy City is home to thirteen of those new global unicorns: G2, ActiveCampaign, Amount, Bringg, Cameo, Copado, Enfusion, M1 Finance, Nature’s Fynd, Project44, Relativity, VillageMD, and ShipBob.

But the influx of new funding can’t resolve a fundamental challenge facing high-growth companies nationwide, from start-ups through Fortune 500 companies—attracting and retaining talent to fill the key positions, which ultimately drives enterprise growth. In fact, staffing may be one of the most limiting factors in a unicorn’s ultimate success if not properly addressed.

Cash-rich companies find themselves competing for a shrinking pool of talent with greater opportunities and changing priorities. The pandemic fundamentally changed the way employees think about the workplace.  The increasing shift to remote work and Zoom meetings afforded people the opportunity to revisit their jobs, lifestyles, and where and how they live. 

Talent once forced to cluster around high-cost-of-living cities like San Francisco and New York have seen that they can maintain a much higher standard of living in smaller cities while fulfilling their work obligations and pursuing career goals.  Workers who once accepted the strain of long commutes have seen the value in regaining that time and being untethered from a physical office. 

Nationwide we’ve seen new start-ups emerging from their Series A rounds with innovative strategies to meet this growing demand for professional staffing by pairing talent with companies whose purpose aligns with their personal goals.  Chicago has long been a hub for human capital management, and we’re witnessing the blossoming of the Midwest as a testing ground for talent solutions with global implications.  

Hunt Club has a big opportunity to contribute to Chicago’s reputation with its latest round of funding. The company’s CEO and co-founder, Nick Cromydas, explains, “We’ve entered a business environment where raising tens of millions of dollars is easier than hiring your next executive. With the proliferation of capital, people need to hire more [often] to scale, and without a talent partner that understands how to win in this environment, you’re going to fail.” 

Hunt Club is primed to respond to that challenge. By drawing on the knowledge of a nationwide panel of experts, Hunt Club helps their clients reach and hire candidates in markets where their companies may not yet have any relationships, access, or exposure to talent. When a search commences, Hunt Club’s technology maps the company’s nationwide network of over 12,000 experts, who collectively offer connections to more than six million high-quality candidates to identify top prospects compatible for the job. Once candidates are selected, the technology pings a connected expert and offers cash rewards to incentivize referrals. The expert can keep the cash or donate it to a charity of their choice. 

All of that enables Hunt Club’s customers to land quality talent quickly—according to Cromydas, on average 40% faster than traditional executive search firms.  Eighty percent of their searches tend to identify the new hire within their first five conversations, which means their customers can spend less time interviewing and more time building their businesses with the right hires. 

Hunt Club has the potential to change the global market for staffing solutions. Stephen Schmalhofer, partner at Teamworthy Ventures and new Hunt Club board member explained, “After experiencing firsthand the power of Hunt Club’s multi-sided talent network to help our portfolio companies, our team saw that Hunt Club was developing a category-defining recruiting platform that is built to solve the urgent problem of finding the right talent and providing a great experience for candidates, employers, and recruiting teams.”  

That potential highlights not only Hunt Club’s innovative approach, but also the significant impact that innovations coming out of Chicago and the Midwest can have on reimagining recruiting on a global scale.  The challenge is one that will be met by matching talented employees with companies primed to respond to the new priorities of a global workforce.  

 *My firm has partnered with Hunt Club for talent searches and programs.


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