Kaleigh Oleynik

From Interpretation to Infrastructure

Her first role was translation and interpretation for Spanish recruitment at the DOE, work that put her in the position of handing families information they did not otherwise have access to: details about schools, and a path into the school she worked for. That was the part that hooked her. The second part surprised her. Confronted with files that were out of order, she reordered them, and started writing notes in a cleaner format so that the next person could use them. She is candid that it was elementary work for someone brand new to the workforce, but the instinct behind it never left. "You can be so much more human and connected when you're also organized," she says, a sentence that doubles as a design principle for every talent function she has since run.

The third piece is temperamental. Oleynik compares herself to a toddler in the why phase, the difference being that she never grew out of it. Recruiting, she realized, is one of the few professional settings where you are permitted, even expected, to ask people enormous amounts about themselves. She has done exactly that across industries, and rarely takes the first answer at face value. Digging one layer deeper is, in her telling, the whole job.

From the Department of Education she moved into tech, starting at a mission-driven organization that operated as both an engineering school and a technology company. A stint in fintech followed. Then Talkspace, where the mandate is unusually broad: clinical hiring at genuine volume, thousands and thousands of therapists every year, alongside corporate hiring and AI roles. She holds the chief of staff seat at the same time, and she does not see that as a stretch. Both jobs, she points out, run on the same engine. Why, why, why, over and over again.

The People Who Shaped Her

Ask Oleynik about influence and she reaches for three names, only one of whom she has met at work. Susan, her former colleague at Revolut, is the first. Senior, unmistakably professional, and yet entirely genuine, Susan was the first leader at that level who showed her that you can bring a great deal of yourself into the room and still be taken seriously, without masking behind a performance of super-professionalism. She brought the joy from the rest of her life into her work, stayed curious, and shared generously. Oleynik describes it as modeling: not advice given, but a way of operating made visible.

The second is her grandmother, now 97, whom Oleynik calls brilliant and delightfully kooky. She never had the chance to go to college. What she had instead was an unrelenting interest in other people and a willingness to keep asking questions until she actually understood them. That is not a small inheritance for someone who interviews for a living.

The third is Emily Wilson's territory rather than a colleague's: the first woman to translate the Odyssey into English. Oleynik admires her for using language with real creativity, for bringing social justice and a fresh perspective to a text thousands of years old, and for the dedication it took to do so while absorbing backlash simply for being a woman in the field. "I appreciate her as a professional that I've never met," she says. It is a revealing choice for a former translator who now spends her days interpreting one person's story for another audience.

What AI Actually Changed

Oleynik is neither an evangelist nor a skeptic on AI. She is a practitioner who has clocked both sides of the ledger. She came up in the manual era, and she was proud of how fast she could write a Boolean string. Nobody has to do that anymore, and she thinks that is fantastic. The bigger gain, in her view, is qualitative: it is now genuinely possible to find hidden gems in the talent pool, to take a considered risk while sourcing, because the search can be fine-tuned toward real experience rather than a title match.

The cost is on the inbound side. "Every resume looks incredible now," she notes, which makes it harder to determine who has actually done what. She refuses to be cynical about it. AI resume tools are almost certainly lifting candidates who were being screened out for reasons that had nothing to do with capability, and she counts that as a genuine good even as it makes her own review process heavier. Meanwhile the scheduling and coordination load, work she says was never anyone's joy, is being automated away, which buys back the only resource that matters in recruiting: time talking to people.

Her most interesting prediction is about the recruiters themselves. Talent acquisition has historically been the first function to grow and the first to be cut, hiring 30 people and releasing them six months later. Oleynik hopes, and admits she cannot be certain, that the efficiency these new tools create will finally produce stability: smaller, more thoughtfully assembled teams of genuinely creative people who are hired well and then kept.

Stay Curious, Stay Kind

Her advice to other talent leaders is deceptively simple and aimed squarely at the experienced. Most recruiters start out curious. The risk is erosion. The longer the career, the louder the voice that says you have seen this candidate before, that you already know how this reference check will go. Oleynik considers that the single most dangerous habit in the profession, and prescribes the same remedy at both scales: try new tools, new tactics, new ways of being efficient, and then bring the same openness into every individual conversation.

She means it literally. Even in a phone screen where it is clear within minutes that the fit is wrong, she believes there is something to learn. "You can still learn from every person on earth, and I'm not being cheesy," she says. Even a poor answer is information; dig slightly and you usually surface what is motivating the person to say it. Her closing formulation is four words long: stay curious, stay kind.

A Product That Belongs to Everyone

Oleynik is deliberate about one more commitment, and she is aware it is harder to state now than it was a few years ago. She remains fully invested in diversity, equity and inclusion, not as a position but as an observed result. She has watched the workforce improve when organizations are permitted to look openly for different perspectives, and she has seen it firsthand at Talkspace, whose leadership team she describes as diverse not only in the ways people immediately assume but in how members think, where they were educated, and what language they speak at home.

For a mental health company, that composition is not decoration. It shapes the product directly, making it more accessible and, in her word, more democratic. What frustrates her is the reframing. She is sad that something the field figured out was straightforwardly good for humanity is now read in some quarters as a trend or a political movement. Coming from someone whose first professional act was translating information so that families could reach a school they otherwise could not, the position is entirely consistent. Access has been the through line all along.