EPISODE · Aug 20, 2026 · 5 MIN
Laid Off at Zillow: 500 Cuts, One Email
from The Messy Middle
This week's guest left a team-level role at Zillow after leadership cited an "AI-driven restructuring," and within six weeks turned that layoff into a new tech role by rebuilding her severance ask, her interview story, and her job search strategy from scratch. The episode traces the exact morning it happened, the vague meeting invite, the scripted VP call, and the frustration of hearing AI blamed instead of getting a real explanation. This is a useful listen for anyone navigating a career change or career pivot in tech, especially after an AI-related layoff, and it gets specific fast. - How she calculated leverage for a severance negotiation once AI investment, not performance, was named as the reason - Why she only used half of her legal review window before signing - Her job search numbers: 68 applications, four first-round interviews, and how the offer actually came together - The layoff-answer rewrite, from a defensive first draft to a two-sentence version tested on three honest listeners Airing the week of 08/19/2026, this one's worth sharing with anyone weighing their own next move. 📣 We Want to Hear from You! - 📝 Submit a question
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Laid Off at Zillow: 500 Cuts, One Email
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