Legendary Assistants to the World’s Most Famous CEOs
Long before the TED Talks and memoirs, some of the world’s most high-powered CEOs were backed by assistants who shaped how they built empires. These behind-the-scenes pros were managing crises, planning secret weddings, running billion-dollar schedules, and sometimes launching impressive careers of their own. Here’s what their work looked like then, and what they’re doing now.
Steve Ballmer: Then
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Ballmer was hired by Bill Gates in 1980, but “assistant” undersells it. He focused on business operations and strategy rather than admin tasks. He became a sounding board and a key decision influencer. Gates once called him one of his “most trusted advisors,” a description that tracks, considering Ballmer would later run the company.
Steve Ballmer: Now
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After rising to Microsoft CEO in 2000, he held the reins for 14 years. His stake in the company has ballooned in value, and Bloomberg now lists his net worth at around $150 billion. These days, he’s focused on basketball, philanthropy, and data transparency through his nonprofit, USAFacts.
Ann Hiatt: Then
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Her career kicked off at Amazon in 2002, where she worked directly for Jeff Bezos. Hiatt once described the job as “unforgiving” and “relentless.” She handled everything from last-minute helicopter bookings to high-pressure scheduling. She later supported Eric Schmidt and Marissa Mayer at Google.
Ann Hiatt: Now
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Hiatt moved from tech assistant to global advisor. She runs her own leadership consulting business, coaches startup founders, and has published a book called Bet on Yourself. The book details how her years supporting top CEOs taught her to think like one. She now helps other professionals do the same.
Debbie Gross: Then
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When Debbie Gross joined Cisco in 1991, John Chambers was still a VP. She quickly became the anchor for his daily operations and later, the lead for a global admin team of over 1,000 employees. Chambers rarely walked into a room without material she helped create.
Debbie Gross: Now
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Gross left Cisco in 2017 but kept her foot firmly in the professional world. She now coaches executive assistants and runs a training program. She also authored The Office Rockstar, which outlines her methods for managing executive relationships and navigating fast-paced environments.
Naz Beheshti: Then
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Straight out of college, Beheshti landed a job many dream of: working as Steve Jobs’s executive assistant at Apple. While his leadership style often made headlines, Beheshti described him as someone deeply invested in wellness and mindfulness, which she witnessed up close during her time at the company from 1999 to 2000.
Naz Beheshti: Now
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Inspired by Jobs’s focus on health, Beheshti launched a corporate wellness company, Prananaz, in 2012. She also became a public speaker and author, publishing Pause. Breathe. Choose in 2021. Her work now blends business performance with well-being strategies, a career path directly shaped by her early professional years.
Monique Helstrom: Then
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Monique Helstrom coordinated Simon Sinek’s entire business life for nearly a decade. She oversaw speaking tours, media appearances, book launches, and travel, acting as what she called the “Chief of Simon.” Her role went beyond logistics. She ensured every appearance aligned with the broader message of Sinek’s leadership work.
Monique Helstrom: Now
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Today, she’s a sought-after speaker and executive coach who trains other assistants and executives on how to work better together. Her sessions focus on evolving assistant roles into strategic partnerships. She’s also become a voice in redefining what modern executive support can actually look like.