Benjamin Cheung

From Pre-Med to the Talent Side

Cheung went to a state college without a fixed plan, tried the pre-med route, and landed on a psychology major with a business minor. He sampled widely: a marketing internship, research work in a lab. Then, in his final year, an HR internship at 1-800-Flowers.com put him in front of the full function, and one part of it pulled harder than the rest.

"There was definitely a lean towards the talent acquisition side of things," he says. He kept leaning. The boutique search firm gave him his craft. A startup gave him something less common. That company went through several pivots inside a single year, and his role moved with it, shifting from talent into operations work spanning sales ops and marketing.

That churn produced the defining fork in his career. He could continue down a sales operations track or commit to technical recruiting. He chose recruiting and, in his words, has not looked back.

An Operator's Apprenticeship

Most people in talent come up through the agency world, then move in-house. Cheung's path looked nothing like that. Inside that one pivoting startup, he reported to the head of talent and people, then to the marketing lead, then to the VP of sales, then to the COO, all within under a year.

On paper it reads like instability. In practice it built a skill set that few recruiters carry into the job. "I've always had a little bit more of an operational basis from that perspective," he says, and that operator's instinct is what separates his recruiting from pure candidate throughput.

The People in His Corner

Cheung names two managers from those early years without hesitation. The first is Talia Spiegel, now a VP of HR at Rippling. The second is David Walpert, who he believes is now a chief of staff at another startup. Both did something more valuable than teach him process: they gave a young recruiter the confidence to believe his own judgment was worth voicing. He still keeps in touch with both of them, which he calls awesome.

The deeper source is at home. Both of his parents are immigrants who, as he puts it, had to work hard for everything they had and get scrappy. He treats that inheritance as directly applicable to his profession. Recruiting requires thick skin, because the job is a long sequence of no's followed by the decision to push forward anyway. But resiliency, in his reading, is not just endurance. "Part of that resiliency is also being able to come in and have a voice in the room and have a seat at that table," he says, "to help push something that you believe in forward." He notes that not everyone in the profession gets that seat.

Scaling Yourself, Not Replacing Yourself

Cheung's view of AI is pragmatic rather than apocalyptic. It automates a lot of manual work and does it faster, and it will not replace people outright. "There's always going to be a human touch, a human element that helps people stay connected," he says. What it does change is leverage. Tooling such as Juicebox, alongside the wave of AI products now reaching the market, can be trained to replicate how a recruiter speaks and how a recruiter acts. It takes patience to get the models to do what you want, he notes, but eventually they do a pretty decent job, and the result is one person operating at greater scale.

The more interesting frontier for him is building rather than buying. Every recruiting team he has known has hit the same wall: no access to the technical resources needed to build custom tooling for themselves. That wall is gone. Taking vibe coding to the next level, as he describes it, he has built out tools that gather scattered business context and present a breakdown of where the company sits in the overall landscape. What matters as much as the data is the packaging: information organized and presented in a way a team can simply pick up and use. No internal engineering squad required.

The payoff is not novelty, it is conviction. Recruiters who understand the macro picture can sell the vision instead of the job description. "If you know what you're selling, if you're able to connect it to the bigger picture and really sell that vision and have that information at your fingertips, it's extremely powerful."

Every Hire Is a Ripple

Asked for the single piece of advice he would give other talent leaders, Cheung does not talk about tools or sourcing channels. He talks about influence. Recruiters, especially in startups, sit in one of the few seats that shapes a company's culture directly, one person at a time.

So he pushes his peers past the metric they love most. Do not only optimize for the candidate close. "Think about what that impact that one person will have on the next five hires that you're going to hire," he says, and then what they will do for the company after that. Will this person help scale the business in a way that makes sense? That framing produces conversations that are, by his own admission, uncomfortable. He believes in having them anyway, provided the strong opinion is backed by data and by honest observation of what the company needs at a talent level to get where it says it is going. Ripple effects follow from the people you bring in, and talent leaders sit in a powerful place to shape them.

His closing line is the whole philosophy compressed: "Just have a voice and don't be afraid."

The Operators He Champions

Cheung is quick to redirect credit toward peers he rates highly. Santiago Medina, who helped scale the teams at Apollo.io before joining a new startup. Mike Spalding, who ran talent at Paxos and then MotherDuck, and who Cheung believes was at Qualtrics during its acquisition. And Colin, who came up through the agency world, spent a long stretch at Bowery Farming, and joined Method as its founding recruiter. "I think they're standout folks," he says.