The Grueling Job Search w/Bradley Stokes, VP of IT

5 Jun 2025 · 32 min
31:53

In this live YouTube interview, host Taylor Desseyn talks with Bradley Stokes, a veteran IT executive who recently completed a seven‑month job search after leaving a private‑equity‑backed mechanical‑engineering firm. The conversation covers the initial reliance on mass‑apply tactics and LinkedIn postings, the resulting ghosting and runner‑up experiences, and the realization that high‑level senior searches require a more strategic approach. Bradley explains how he pivoted to applying directly on company career sites, conducted hyper‑targeted outreach to CEOs, CFOs, and board members, and created a two‑column “requirement‑to‑experience” document that mapped each job posting line‑by‑line to his own achievements. He also discusses the emotional toll of the search, the importance of transparency on LinkedIn for community support, and how he handled periods of recruiter silence. The interview touches on a high‑pay offer he turned down for family reasons, the value of in‑person coffee meetings, and broader career advice such as maintaining confidence, taking calculated risks, and never burning bridges. The session ends with rapid‑fire questions about coffee preferences, shout‑outs to industry peers, and a final piece of guidance for younger professionals.

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