Continuum’s Chauncey Brooks on Startups, Recruiting, and What It Means to Find "Good Talent"

Halden Pfearsen
Halden Pfearsen
Managing Editor

15 minute read

Like many talent professionals, Chauncey Brooks didn’t set out to be in talent. Having recently graduated from college, his biggest goal was avoiding an office job. This led him to manual labor jobs, where connections with his co-workers, many of whom were immigrants, developed a passion for immigration politics and law. He found himself at a law firm in San Francisco, there to fight the good fight, helping people secure asylum .

It wasn’t quite the work he thought it would be. Here he was, in the office he wanted to avoid, mostly filling out H1B paperwork for major companies like Cisco and Yahoo. “Second day of the job,” he told Ashby, “I was thinking, oh shoot, I've made a huge mistake.”

A year into gritting his teeth to force through a job that wasn’t for him, a door opened in the form of a friend inviting Chauncey to join him at Google. Though he wasn’t sure if Google would be any better of a fit, he went out on a limb and applied, and that’s where things began to change.

Google’s recruiting process was intense, and the pressure only ramped up once he was hired. “On day one, they put you through bootcamp,” said Chauncey. He and twenty others in this incoming professional class studied under heads of talent from various companies who taught them about everything from what code really is to sourcing effectively to a deep dive of Google’s business model.

"A lot of what the recruiter's job is is understanding what does the company need?"

The bootcamp took people with an aptitude for recruiting and showed them the fundamentals of the craft. “I loved it,” Chauncey said. “I loved the sales aspect of it, the technical aspect of it, the technology aspect of it. It was so different from what I had grown up thinking of as work.”

Since his Google bootcamp days, Chauncey has worked for small ad tech companies and industry giants like Stripe and Slack. Through it all, he’s sought the very thing he was taught to source at Google: the elusive idea of good talent.

Chauncey was quick to elaborate on what exactly good talent looks like - now and over a decade ago. “The way that we and the companies now think about talent is much more dynamic and fluid than it was when I was going through this program in 2007. They were teaching us on a very blunt basis, a lot of it ended up being about lists. They trained us in how to spot a good resume, but in doing that they had a list of companies they liked, a list of schools they liked, and those were treated as signals. If they got out of the good school, that's a signal. If they got into a graduate program, that's another signal. If they worked at McKinsey, that's another signal. It was on a very calculated level where they basically taught us to think in terms of an algorithm for each role. But that's changing. Nowadays I think we realize that's quite exclusionary. The person who got to go to Harvard and work at GE and Google probably came from quite a privileged background.”

Realizing this, Chauncey said, has made him into a better recruiter. But though the inputs have changed, the process he’s using and the way he thinks about recruiting has remained. “It doesn't mean that the person who did those things is not still good talent, but it means they're good in one axis. While the person who put themselves through school and got an associate's degree and then went into the military, that is a very different kind of path, but in many ways it tells you much more about them than the person who simply cleared gates in a more traditional or linear career.”

On "good talent"

So which one is good talent? They both are, but, “A lot of what the recruiter's job is,” Chauncey went on, “Is understanding what does the company need? How does the company think about talent and how do I translate that to looking at someone on paper and determining if they've passed through the crucibles we actually care about.”

After years in the field, and helping to get a startup all about hiring up and running, this has been one of Chauncey’s main takeaways. You can’t prescribe what good talent is, but you can create an effective plan to find it - a plan that looks very different at every stage.

"Recruiting is everyone’s job. It never becomes just the recruiting function's job, or just a manager's job - they are there to facilitate it and help it scale.”

When you’re in the early days, doing Seed or Series A funding, Chauncey tells us that recruiting is everyone’s job (though the share falls heavier on the executive team.) “You need to develop your process and get clear about what your company's bar is," he said. "Get yourself a great recruiting advisor to help you build your process and teach you how to build the company." (Perhaps through Continuum?)

Once your company enters Series B and C funding, and starts truly scaling, that’s when things get serious. “Hire your Recruiting advisor or someone like them,” Chauncey advises. “Scale the recruiting team. Hiring is still everyone's job but Recruiting is scaling and running the process and developing candidates. Build your talent brand and start hiring sourcers and recruiters to build scale.” When you're ready, you can take this even further. “Get an HR or Chief People advisor, and work with someone to develop some quick and dirty compensation bands to get you to the next phase.” This is also the stage to start seriously building out your recruiting operations team, not later.

After Series C, moving towards pre-IPO, you should already have a robust system in place for finding good talent. By then, says Chauncey, “Executives should be focused on hiring amazing executive talent. Bring on a CPO, bring on a recruiting leader that has seen a lot of scale. Hire your comp leader. Then you can scale and start hiring pipelines of talent.”

At this stage there’s a mental shift. Your leaders are no longer hiring for their teams, they’re hiring for the company. And, this far along, there’s no time to waste. “If a candidate meets the bar, get them an offer as soon as possible. You can figure out which seat to give them later.”

We asked Chauncey what else founders tended to miss in their search for good talent. “Recruiting is everyone’s job,” he re-stated. “It never becomes just the recruiting function's job, or just a manager's job - they are there to facilitate it and help it scale.” And what else? “Stop interviewing when you know what you need to know. Be hyper focused on what you need each hired person to accomplish in the next year.” To achieve this, “try to envision a stellar annual review conversation - what are you telling them they did well?” Next, “Until your business has strong product market fit, hire great "general athletes" rather than deep specialists. And make sure they're good, because the caliber of your early talent dictates the caliber of your future talent."

It’s a lot of advice, but founders have a lot to consider when hiring. “Startup hiring is a brawl, Chauncey joked, “not a boxing match. There are no rules except that you better win. So you have to be willing to hustle and do unnatural things to get that win. You don't want to do it all the time, but be clear when you need to break the compensation band or change the organizational structure to accommodate game changing talent.”

One more major part of what makes good talent, that founders need to know, is what kind of company you truly want to build. For instance, a lot of founders will say they want a great engineering team. But Chauncey says that isn’t what they really want. He asks them, “What kind of companies have you worked at, what kind of cultures have you liked? What kind of companies do you look at and say, ‘I love what they've built'-? Saying you want a great team is too easy. A great engineer at Google could be a terrible engineer at a five person company because the mindset and the things you have to do to be successful are so different.”

Instead, Chauncey wishes that more startup founders would start with a vision of their culture. “What kind of culture do these founders want to build? And then you cascade that down,” He said. and after that they can focus smaller. “What are the challenges? What are your headcount plans? Then you can start building things like the talent philosophy and the interview processes. And it’s the recruiting team that all actually builds that up and, and scales it out to be able to accelerate.”

Once again, the value of an amazing recruiter shines through. But being an amazing recruiter takes hard work, which Chauncey has learned all too well.

“I think one of the challenges that I've had in my career is that I'm always either at the biggest job of my life or I'm at the smallest company. Either way, I'm always at the steepest end of my learning curve. I've reported to everyone from the General Counsel, to the VP of engineering, to the CFO, to the COO, and very rarely do people in recruiting report to someone who's actually ever sat in your seat and done your job. And that's interesting, because they give you a lot of leeway to figure things out, but it's also challenging in that they don't usually have answers for you.“

“One of the challenges of recruiting is that you get this place where if everything is high priority, then nothing is high priority.”

Chauncey’s method of tackling that lack of answers might seem dark, but it’s undeniably been effective for him. “I've always sort of tried to think what's the thing I get fired for? If I don't do this thing, they show me the door. You can also think: what are the biggest challenges facing the company and how can I have the most impact on that with one blow? I’ve tried hard to understand what’s top of mind for my boss, what keeps them up at night. Even if it’s totally unrelated to hiring or my job, it helps me to distill to my team what they should be thinking about and what's important for the business.”

These questions are good for more than getting into the boss’s head. “It also helps me to prioritize the work that comes to recruiting. One of the challenges of recruiting is that you get this place where if everything is high priority, then nothing is high priority. Many businesses are bad at identifying the real highest priority things, so it’s up to the recruiting leader to actually decide what that is.”

What recruiters should know... and what founders miss

Other advice for those in recruiting? “I like to be prepared for all meetings,” he said enthusiastically. “I'm one of those people that really likes to pre-read, so I can kind of anticipate where things are going to go and understand how I want to direct things. That really helps in having a strong grasp of the metrics and mechanics of your business, and it lets you answer questions that might be pointy or challenging on the fly.”

“I don’t trust people who don’t have scar tissue... if you haven't failed, it means you didn't try hard enough.”

“There's always deadlines,” he told us. “There's always candidates that say no. To some degree that's just part of a game, and you have to accept that. In my twenties and early thirties, I would just respond to things at all times. But I work at an eight person company now. I'm always either taking care of my kids or I'm working. It's important to have boundaries and a functional process. For me, from five PM to eight AM I'm not available. It doesn't matter if you're the CEO himself, because that's the kid's time. The boundary-setting and compartmentalization helps a lot.”

That doesn’t mean it’s always been easy for him. “At every place I’ve worked, I've made mistakes,” he told us, not quite laughing. “The key thing is: what do you learn from them and how do you move forward? I don't trust people that don't have scar tissue, that haven't failed; if you haven't failed, it means you didn't try hard enough. If Silicon Valley has a problem, it's that people don't talk about their failures enough.”

Failures like risking your job, and the jobs of everyone in your company, for instance. For most people, the boss stopping by your desk to threaten to fire you would be the source of a heart attack. For Chauncey Brooks, it was the source of inspiration.

Just a few years into recruiting, he was doing sourcing work at his second company. His boss at the time, Martin, was a fantastic mentor and leader, but Chauncey noted that he was not especially technical about recruiting, and the numbers were slipping as a result. That was when the CFO came to town.

“We had just landed our series C funding and the company was about to double or triple,” he told Ashby. ”Our CFO was this guy from Google, a real New York City, tough as nails kind of guy. I've had like two conversations with him, ever. He swings by our desk and he leans over and says look, you all miss your numbers every single quarter. If you don't hit your numbers this year, I'm gonna fire everyone on the entire organization. Then he just walks away!“

Some recruiters would buckle under that kind of pressure. But not Chauncey.

“Martin and I grab a meeting room and say, okay, we gotta’ figure this out. At this point we were just two or three people trying to get it all done at a hundred person startup, shortly after the recession. What we realized was that we needed some way to determine what inputs were needed to get to the outputs that we wanted. Prior to that we had a rough finger-in-the-wind approach, approximating sort of what we need to get there. In that meeting we distilled down what we needed and built a timeline. And what we found was that, if we need to hire X a number of people in six months, then that actually means we have to have Y number of interviews and Z number of, of, uh, phone calls. And to do that, we would have to have at least like five recruiters, but they’d have to be already on board now. So in reality we should have hired them six months ago!”

“We presented this and I remember the CFO said: Cool! If you're wrong, you have to fire these people. It was the first time that I really realized how important process and strategy was. I was like, oh. This is real.”

"If you haven't failed, it means you didn't try hard enough.”

Chauncey has carried this lesson over into a much bigger philosophy on strategy and planning as a recruiter. “I don't think many recruiters and recruiting leaders like to truly understand the numbers on a fundamental enough level. I think that is largely because they don't look closely enough at these deep links. The idea that if you get your forecast wrong people lose their jobs. And it's really difficult to do that in a scaled organization that understands its headcount. In a company that has shifting finances and changes their head count plan every six months, it's like landing a plane on an aircraft carrier. That was one of the most instructive experiences in my career in terms of understanding how important it was to actually understand the job that we do and how operational it really was. Before that, I sort of thought of it as oh, I talk to people, I find the best candidate, and then I put 'em through! And then I realized, no, this is math.”

The changing world of recruiting

Like so many recruiters, it was the team and the people that made those failures worth it. And with the future of work looking so remote, Chauncey made a note that those entering the field now we're facing a very different set of challenges than those who came before.

“I think it must be really hard to be new to recruiting right now, because I learned so much being in an office and just overhearing what was going on. At Google we would sit in a pit and listen to each other's pitches constantly, and we would tease each other and compete every morning to see who could do the most outreach. And that was fun and it was energizing. And I don't know if I would've liked this industry if I had not started with something kind of like that. So I do think it must be tough right now. You have to find a way to make it entertaining and fun, and make it into a group sport. I actually got this line from John Vlastelica, who's an amazing recruiting guru. He said you run to the fire. Find the hardest thing, the thing that no one wants to work on... and go make it work.”

If you’re interested in connecting with Chauncey, you can find him on LinkedIn. You can also check out to see how Continuum is disrupting the status quo.

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