Ex-Bank of America VP Chair, 56, Couldn't Land a Single Offer in Two Years

A former vice chair of Bank of America spent the better part of every day for over a year applying to jobs — and barely received an automated acknowledgment. Siobhan MacDermott, 56, shared her account in a Business Insider as-told-to essay after two years out of institutional work, a stretch that pushed her retirement timeline back eight to 10 years as she dug into savings.

Her résumé is not the problem. MacDermott served as vice chair at Bank of America, principal at EY, held senior cybersecurity roles at AVG and McAfee, and was a partner at The Consello Group until early 2024, when family reasons forced a relocation from New York to Menlo Park, California, at age 54. She has sat in boardrooms with Fortune 500 CEOs and advised governments.

What broke in the search?

The barrier, she says, is categorization. "The most surprising barrier has been the gap between what I've actually done and what the market knows how to categorize," MacDermott said, describing a career that doesn't fit neatly into a job description.

The tactics that failed her:

• LinkedIn Easy Apply, which she calls a complete waste of time
• Recruiter calls that went nowhere
• 45-minute competency interviews with people who'd never heard of her former employers

Applications, she said, went "into the ether" — countless résumés, near-zero responses, sometimes not even the courtesy automated reply.

What actually worked?

Direct outreach to CEOs and board members, bypassing HR entirely. She'd send letters with free strategic observations — "here are some things that I think you should be doing as you think through your next quarter" — to earn attention. It got her in the door. It didn't get her hired. Junior screeners told her, "You're overqualified for this job." HR teams said, "It doesn't quite match." That happened quite a few times.

She also ran an informal experiment on LinkedIn. She toggled her listed gender between male and female repeatedly, and felt she got more responses when readers assumed she was male. Then she removed the first six years of work experience and stripped the dates from her degrees, making her appear seven to 10 years younger. Engagement improved.

Her diagnosis is geographic as much as demographic. In Silicon Valley, she argues, you age out faster than elsewhere in the US, in a highly male-dominated space — two headwinds from the get-go.

The pivot

About a year in, facing financial pressure and what she calls intellectual boredom — "I felt like my brain was starting to rot" — she stopped applying and started building. In January she launched two companies: Khaos Holdings, a strategic risk-intelligence firm, and TeenAegis, a child-safety intelligence business.

She's now raising capital. If it lands, the job search ends. If not, she keeps searching — but only for work adjacent to the problems she's now solving.

The deeper shift is philosophical. Her definition of stability moved from "security comes from a salary" to "security comes from what I've built and what I know." The journey, she admits, was "a little bit of a midlife crisis" — swapping "what job do I want?" for "what's my purpose in life?"

For senior practitioners in their 50s reading this, the lesson is structural, not motivational: institutional hiring pipelines punish non-standard careers and visible age, and founder-adjacent positioning may price your experience better than any application. MacDermott, an "absolute eternal optimist," still believes there's light at the end of the tunnel — it's just the question of how long the tunnel is.

By Daniel Okafor