Jill on Money with Jill Schlesinger Career Transitions With the Help of AI
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Mar 6, 2026 Chieh Huang, entrepreneur and former CEO of Boxed who co-founded Pelgo, an AI-driven career transition platform. He discusses creating Pelgo to help workers navigate AI-driven job shifts. Short takes on practical upskilling, using AI to automate workflows, and how AI changes hiring and job roles. Tips on learning-by-doing with AI and tools to prepare for career transitions.
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Pelgo Created To Fill AI Job Safety Net
- Chieh Huang built Pelgo to address widespread job disruption risk from AI by creating accessible transition support.
- He couldn't find scalable safety-net solutions for displaced workers, so he aimed to lower outplacement costs using LLMs.
Tech Disruption Creates Unpredictable New Jobs
- History suggests tech destroys tasks but creates new jobs we can't yet imagine, so predictions about total job loss are unreliable.
- Chieh compares AI's unknown job-creation curve to podcasts and other internet-era roles that surprised skeptics.
Pick Your Postlayoff Path Before Job Searching
- Do choose a post-layoff path first: decline help, retire, start a business, seek counseling, or reenter the workforce.
- Pelgo personalizes next steps, matches to jobs, crafts AI-optimized resumes, and offers targeted upskilling modules.