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Tech industry headhunters explain what companies get wrong when hiring for high-stakes roles like CEOs, board members, or top VPs

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Headhunters Jana Rich and Jared Furtado Headhunters in tech from left to right: Jared Furtado and Jana Rich

  • Headhunters help big companies like Dropbox, Uber, and Plaid hire visionaries for top roles and the process is much more involved than simply scanning resumes.
  • Headhunters have to have multiple conversations with senior people at the company, dissect job descriptions, and more as they try to find the right fit.
  • Two top tech headhunters share common mistakes they see, like companies that use language that causes them to miss out on up-and-comers with fresh perspectives who can rise to the challenge, or descriptions that are too vague. 
  • Sometimes companies will get bogged down with a long wish list and it’s up to the headhunter to cut through the weeds to figure out what’s really important.
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Headhunters discreetly keep Silicon Valley companies competitive by finding top talent to fill C-suite positions, taking meetings with high-level movers and shakers in the hopes of placing them in new, lucrative positions.

The process of finding a suitable executive for a hot tech firm is different from how recruiters fill engineering, sales, or product roles: through job sites and scanned resumes, according to cofounder of boutique headhunting firm Towerhill Associates, Jared Furtado. 

The most sought-after execs don’t upload their resumes to job sites or update their LinkedIns, says Furtado, whose firm has worked with the likes of Uber, Dropbox, and Plaid. That’s where headhunters come in. 

“You want to keep a search exclusive-feeling: You don’t want to just have it blasted out,” Furtado said. “That’s why job postings, they can be good — because you can certainly get that out there that this company is hiring — but then from a job seeker standpoint, it loses that high-touch feeling. It stops feeling exclusive. And top tier candidates aren’t spending their time looking at job postings.”

Furtado and cofounder of Rich Talent Group, Jana Rich, laid out the typical process: Client companies will come to a firm to fill a high-level placement — a CTO, or a VP of data science, for instance — and a headhunter will have multiple conversations with members of the executive team to discover the most important attributes a candidate should have. From there, a headhunter will scan through their personal database of potential candidates and ask externally for referrals from colleagues who are in the industry. 

Most headhunting firms are paid one of two ways: On contingency or on retainer. Contingency means that firms are paid based on whether or not they find a candidate, whereas firms on retainer are paid a yearly fee.

The real asset of a headhunter is their network: knowing the cream-of-the-crop will help them fill open positions. Towerhill Associates has a database of hundreds of thousands of names it has collected since its inception in 2008 and Furtado himself has placed execs at big-name companies and pre-seed startups alike. Rich Talent Group serves more than 80 high-profile clients like Asana, Airbnb, and Facebook and has placed the CEO of Evite, the president of Uber, and the head of communications at Coinbase, among others.

Furtado and Rich both said there are plenty of bumps along the way when it comes to the hiring process, though, and highlighted three key mistakes that companies tend to make:

Headhunters have to cut through long wish-lists, vague boilerplate language, and unclear or unattainable goals

Companies often come to headhunting firms with a too-long laundry list of must-haves, or use language in their job descriptions that ends up eliminating up-and-coming female or minority candidates right off the bat, says Rich, who has been in the headhunting business since 1996. This can force the company to miss out on diverse voices in their boardrooms or executive suites.

“For example, ‘they have to have lead a team of X number of people,’ which can really exclude a lot of women, and people of color,” Rich said. “So [I’ll be] really pushing on them like, ‘Okay, this might be the first time this individual has led a 100 person team. But are you open to that?'”

Furtado and Rich both said that companies too-often use boilerplate candidate character descriptions that they haven’t quite defined themselves, like “strategic” or “hands-on.” 

“Even the concept of strategic, what does that mean?” Rich said. “Let’s really unpack, what does that even mean? Does that mean they’re smart? Does that mean they can think about new business models? And why? When you say strategic, what are examples of projects you have to work on? Because strategic can mean radically different things depending on what it is we’re actually talking about.”

Vague language makes the process of finding the perfect candidate to lead the company difficult, which is why headhunters often have multiple discussions with current high-level people. Getting a fuller, more concrete understanding of the role helps them pluck the right candidates to interview. 

Rich asks questions like: “What are the actual reasons and motivations around why they’re seeking to fill this role? And what are the metrics for success going to look like? What are they must-haves versus the nice-to-haves?”

She also often asks client companies why a certain position exists, and what role it plays in the company’s overall success: “Our work with them is to try to get the criteria as specific as possible.”

Sometimes Rich and Furtado will connect with a company after it has already tried and failed to work with another firm or find someone to fill the role internally.  When a firm struggles to fill critical, executive-level positions, headhunters have to help them refine their goals.

“You kind of have to play, detective. What happened?” Furtado said. “If you interviewed 30 candidates for an executive position, that’s a lot. Where were the expectations? Maybe the type of skill set you’re thinking for, not one person has that. Maybe you have to break this up into two roles.”

Rich said the role of a headhunter often requires thinking outside the box and ahead of the client company to find the right fit. Part of the reason companies will use headhunters is to get an outsider’s view of what the company can benefit from: Headhunters collect anywhere from 10 to 15 new prospective executives everyday, and are often at the forefront of finding exceptional talent.

“One thing I love,” Rich said, “Is that companies will say, ‘I wouldn’t have found that if it weren’t for you and your team.'”