The landscape of the American job market is undergoing a seismic shift, and for seasoned professionals in their 50s, the experience has become increasingly exclusionary. Siobhan MacDermott, a 56-year-old former executive who has held leadership roles at giants like Bank of America, EY, and McAfee, found herself hitting a wall of systemic bias that is becoming a defining feature of the modern corporate hunt.
After relocating to Silicon Valley in early 2024, MacDermott’s attempt to re-enter the workforce revealed a stark reality: institutional hiring processes—heavily reliant on automated filters and rigid categorical criteria—often fail to account for the nuanced value of a high-level veteran career.
## The Algorithmic Bias Against Experience
MacDermott’s journey highlights a growing friction between human expertise and modern HR software. Like many job seekers, she discovered that standard platforms like LinkedIn’s “Easy Apply” often served as a black hole for her credentials. Despite an elite resume, she faced a lack of response that prompted her to experiment with her own digital presence.
In a revealing turn, she noted that adjusting her profile to suggest a male gender resulted in a higher volume of engagement. Furthermore, she found that removing the earliest years of her professional history and graduation dates—effectively “age-masking”—led to better response rates from recruiters. This trial-and-error process highlights how ageism and gender bias remain deeply embedded within the algorithmic structures of the digital hiring ecosystem.
## Navigating the “Ether” of Modern Hiring
The tech industry, particularly in hubs like Silicon Valley, has cultivated a culture that prioritizes rapid, specialized output, often at the expense of long-term strategic experience. MacDermott noted that even when she successfully bypassed traditional HR gates by reaching out directly to CEOs, she was frequently diverted to junior staff who viewed her deep experience as a disqualifier.
“You’re overqualified for this job,” became a common refrain. This suggests that the current tech hiring paradigm is struggling to map “seniority” to anything outside of narrow, task-specific engineering or coding roles. For those whose careers were built on organizational strategy, cybersecurity oversight, and high-level consulting, the market currently offers few landing pads.
## Pivoting Toward Entrepreneurship
Recognizing that the traditional gatekeepers were unlikely to embrace her level of expertise, MacDermott eventually shifted her focus entirely. Rather than continuing to fight for a seat in a system that could not categorize her value, she launched her own ventures: Khaos Holdings, a strategic risk-intelligence firm, and TeenAegis, a child-safety intelligence business.
Her transition reflects a broader trend among mid-to-late-career professionals who are abandoning the job-hunting “ether” in favor of entrepreneurship. By reframing her professional security—moving away from the reliance on a corporate paycheck and toward the inherent value of her own specialized knowledge—MacDermott has reclaimed agency over her career trajectory.
The experience of job seekers like MacDermott serves as a cautionary tale for the tech industry and corporate recruiters at large. As AI-driven recruitment tools become more prevalent, the potential for these systems to institutionalize bias against seasoned talent increases. For professionals in their 50s, the path forward appears increasingly to be one of self-reliance, with many deciding that if the current market cannot adapt to their experience, they must instead build the companies that will.
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