Jessika Calegari
Box
“AI is supplemental to everything we do in recruiting.”
Jessika Calegari has been named to the Talent 100, Class of 2026, the annual award recognizing the 100 most exceptional leaders and practitioners in talent acquisition. Honorees are selected by the Talent 100 committee from thousands of nominations and candidates across the industry, chosen for the impact of their work, the depth of their craft, and their influence on the future of recruiting. This is Jessika's story.
Jessika Calegari began her career expecting to work in biology labs, only to discover she was far more people-centric than she'd imagined, a realization that has carried her through more than nine years at Box and into leadership of recruiting teams across the US and EMEA.
The plan, at first, was straightforward. She earned her degree in biology at Sonoma State University with lab work in mind, the kind of methodical, hands-on science that had drawn her to the field in the first place. Then an internship quickly changed her trajectory. She pivoted to HR and talent acquisition at a biopharma company, where she helped manage the contingent workforce, and after a couple of years she joined Box. She has been there ever since.
Her path inside the company has been one of steady expansion. Calegari started at Box as a sourcer, then grew into managing both the sourcing team and the coordination team. Today she leads recruiting teams across the US and EMEA, a remit that has given her a global view of what it takes to hire great talent at scale.
Learning From Great Leaders
Two leaders shaped Calegari's approach to talent acquisition in profound ways. The first was her manager at the biopharma company where she started, a relationship that has outlasted the job itself; he recently texted her, years after they worked together. What he gave her was less a playbook than a posture. He taught her the intangibles of recruiting: working hard, honoring commitments, and bringing grit and adaptability to a space that changes constantly. "He has made a very impressionable part of my experience," she says.
The second was a leader at Box who took a risk on her. Calegari had done recruiting on her own, but not at the scale required to manage a team of recruiters. This leader saw the intangibles in her and invested heavily in her growth, showing her the ropes of recruiting and remaining a mentor to this day. She has done wonderful things at Box, and Calegari is deeply grateful.
The AI Revolution
AI represents the biggest shift Calegari has seen in her entire career, and she is clear-eyed about where its value actually sits. She views it as supplemental to everything recruiters do, a layer that clears space rather than replaces judgment. Used well, it allows teams to focus on what matters most: building relationships, assessing candidates holistically, and closing deals. Those, she argues, are the irreplaceable elements of the job.
"AI is supplemental to everything that we do in recruiting and talent acquisition," she explains.
Keeping the Human Work Human
Where Calegari pushes back is on the temptation to treat AI as a shortcut to volume without maintaining quality. That, she says, is where things can go sideways, and it is why she sees responsible adoption as a leadership responsibility rather than a technical one. Guiding teams to use AI safely and thoughtfully is critical, in her view, precisely because the tooling is moving faster than the norms around it.
The goal is to use AI to advantage while preserving what recruiting truly is. And that, in the end, is building relationships.
The Talent 100 exists to celebrate the people shaping the future of how the world hires, and few embody that better than Jessika. We are honored to welcome Jessika Calegari to the Talent 100, Class of 2026, and grateful for the experience, perspective, and craft they bring to this community. Congratulations, Jessika. Welcome to the Talent 100.
About the Talent 100
The Talent 100 is an annual list spotlighting the leaders who push HR and talent acquisition forward, organized by Noon AI. Honorees are selected through peer nominations and independent selection committees. Selection is entirely merit-based, with no fees or pay-to-play requirements.
