Jill on Money with Jill Schlesinger

Episode: Career Transitions With the Help of AI
Date: March 6, 2026
Guest: Shea Huang, Founder of Pelgo and former CEO of Boxed

Episode Overview

In this episode, Jill Schlesinger speaks with serial entrepreneur Shea Huang about navigating career transitions in an era of rapid AI-driven change. Together, they discuss anxiety about AI replacing jobs, practical strategies for career resilience, and how Shea’s new company, Pelgo, aims to democratize career support and retraining using AI. The conversation blends candid personal stories, humor, actionable advice, and real talk on both challenges and promise of the AI job market revolution.

Key Discussion Points & Insights

Shea’s Career Journey & Motivation

• Origin Story (04:01)

  • Shea began as an English teacher before becoming a corporate lawyer.
  • Entered gaming industry with friends after the launch of the iPhone; their game studio was later acquired.
  • Founded Boxed, an e-commerce company, and took it public via SPAC (Special Purpose Acquisition Company).
  • Recent pivot: After Boxed, became involved in the World Economic Forum, then co-founded Pelgo to address AI’s impact on jobs.

  “As crazy as it sounds now, I started my career as an English teacher... then ended up becoming a corporate attorney... Then, with some friends, started a studio making games for the iPhone, which led to being in e-commerce at Boxed for almost 10 years.”
  — Shea (04:21)

• SPAC Experience (06:18)

  • Shea notes SPAC was a “mistake,” adding complexity and scrutiny beyond expectations.

Why Pelgo? The Gap in AI Job Support

• Genesis of Pelgo (07:39)

  • Shea and co-founder Frank D’Souza (Cognizant co-founder) saw widespread discourse on AI’s job disruption but little action on what comes next for displaced workers.
  • The company’s mission: provide affordable, AI-powered career transition tools accessible to all, not just executives.

  “It seemed like an afterthought... just folks proselytizing that, ‘Oh yeah, and AI is going to displace hundreds of millions of people from their white collar jobs’... okay, where’s the next part about what we’re doing for those folks?”
  — Shea (08:20)

  “We couldn’t find too many companies there. And so we thought we had to tackle it.”
  — Shea (09:12)

Navigating AI Uncertainty in the Job Market

• Predicting the Future of Work (10:11)

  • Shea draws parallels to the internet’s unpredictable job creation, noting most jobs created by technology couldn’t be foreseen decades earlier.

  “AI is going to destroy jobs, but over time... there’s going to be a lot of jobs created that we don’t even know today...”
  — Shea (10:46)

How Pelgo Works: Affordable, Democratized Outplacement

• Product Offering (11:31)

  • Pelgo mimics expensive executive outplacement services (resume help, career pathing, upskilling) but delivers them with AI at a fraction of the cost.
  • Goal: Make career transition support available to everyone, not just “middle management or above.”

  “With LLMs... there’s no reason why that shouldn’t cost a few bucks a month. And everyone transitioning in their career should have access to that.”
  — Shea (12:21)

• User Journey Example (13:06, 14:03)

  • If laid off, user gets an invitation to Pelgo via email or text. The platform asks about preferred paths (early retirement, solopreneurship, re-entering workforce, etc.).
  • AI assists with resume filtering, surfacing suitable jobs, and identifying upskilling needs, then delivers personalized learning modules.

  “If you want to reenter the workforce... we can help you. Whether it’s creating an AI that gets past resume filters to surfacing jobs... and if there’s a gap in that match, can we upskill you...?”
  — Shea (14:44)

Keeping Your Skills Future-Proof

• Practical Preparation (15:12)

  • Shea’s Two Key Recommendations:
    1. Actively try emerging AI tools—just using them puts you ahead.
    2. Relearn how to learn—adaptability and curiosity will define career longevity as industry change accelerates.

  “The simple steps of trying to relearn how to learn... after you’ve been in a job so long, you’re just like, ‘I know how to do my job and I do it well’... Sparking that curiosity again and that adaptability to change will be very, very important.”
  — Shea (16:25)

Practical AI Example – The Podcast’s Own Inbox (19:47)

• Jill explains the manual work involved in sifting email inquiries and creating radio content; asks how to streamline with AI.

• Shea walks through how AI can automate categorization, draft scripts, and prompt content ideas—freeing up time for creative work, not replacing human contribution.

  “There’s incredible tools... hook into that inbox, feed into a daily script that not only reads the emails but also prompts the script… you could have it prompt you to say, ‘Here’s a question, do you want me to reframe it for on-air?’... That workflow... is actually pretty easy to do.”
  — Shea (20:16)

Philosophical & Emotional Sides of the AI Transition

• Why Resistance and Anxiety Happen (24:35, 25:00)

  • Jill draws analogy to Lotus 1-2-3: tech rarely kills a profession—often augments it.
  • Both hosts urge listeners to get involved before disruption hits, leveraging tools to stay ahead.

  “It’s better to start getting involved with trying to put your arms around it today while you still have a job, rather than waiting till you don’t.”
  — Jill (25:56)

  • Shea emphasizes discomfort is normal—the speed of AI change outpaces perceived benefits, producing societal anxiety.

Getting Past the AI Resume Filter & Skills for the Future

• Job Seekers’ Tactics (28:01)

  • Use AI to optimize resumes for AI-based HR filters.
  • Showcase adaptability and capacity to learn.
  • Example: “Forward deployed engineers”—not new degrees, but adaptability, people skills, and problem-solving define in-demand roles.

  “If you’re not leveraging [AI] to your own benefit, you’re doing yourself a very big disservice... I think highlighting your capacity to learn and adapt will be very important.”
  — Shea (28:19)

Human Skills AI Can’t (Yet) Replace

• Jill’s Blog Wisdom (30:12)

  • Double down on roles that require:
    • Judgment
    • Empathy
    • Adaptability

  “Lean into the jobs that rely on skills that AI so far has not been able to replace: judgment, empathy, adaptability.”
  — Jill (30:13)

• Human-in-the-Loop Importance (31:04)

  • Shea: Proofreading, human nuance, and genuine interaction will retain value, and “human in the loop” processes will define successful AI adoption.

Assessing Risk, Repetition, and New Opportunities

• Fields Under Threat (32:28)
  • Any repetitive job—white or blue collar—is at higher risk.
  • Shea predicts ongoing human need for oversight, especially in high-stakes industries.

Strategic Advice for AI Era

• For job seekers/parents:

  • Use AI in application processes; understand how AI screening works.
  • Focus on adaptability; soft skills and problem-solving are prized more than ever.

• For creators (authors, presenters):

  • Expect your content to be filtered and queried by AI; prepare accordingly.
  • Leverage these tools for preparation, not as sole content creators.

Shea’s Closing Outlook

• AI is moving quickly, but with the right support and mindset, individuals can find hope, curiosity, and opportunity in transition.

  “Hearing from [users], that it sparked this interest and curiosity in them... was really exciting to hear. I generally hope that this time next year... there’s other folks joining us in this mission... how do we make sure we’re helping folks and not just going after the gold rush.”
  — Shea (35:47)

Notable Quotes & Memorable Moments

• On unpredictability of the job market

  "If you said, fast forward many years, there’s going to be these things called podcasts…99% of people would say, I don’t believe you. But here we are.”
  — Shea (10:26)

• On AI resume filters

  “If you’re not kind of creating your resume with the help of AI so that it can actually get through… that are receiving these resumes and filtering through, I think you're doing yourself a very big disservice.”
  — Shea (28:14)

• On what AI can’t replace (yet)

  “There’s something nuanced about sounding like a human that I think will be very difficult to kind of fully replicate in the future.”
  — Shea (31:33)

• On human adaptation in the AI era

  “Sparking that curiosity again and that adaptability to change I think will be very, very important.”
  — Shea (16:25)

Timestamps for Major Topics

• Shea’s Career & Boxed Origin: 03:38 – 07:00
• SPAC Experience and Boxed IPO: 06:18
• Pelgo’s Founding & AI Disruption Anxiety: 07:39 – 09:18
• AI’s Uncertain Job Impact (“Podcast Example”): 10:11 – 11:28
• Pelgo’s Product & User Journey: 11:31 – 15:12
• How to Future-Proof Yourself for AI: 15:12 – 16:57
• AI Automating Podcast Tasks (Live Demo): 19:47 – 21:40
• Societal Anxiety & Historical Tech Parallels: 24:35 – 27:31
• Getting Through AI Resume Filters & Future-Ready Skills: 28:01 – 30:12
• Human vs. AI (Judgment, Empathy, Nuance): 30:12 – 31:33
• Fields Most at Risk, Skill Demand: 32:04 – 33:06
• Content Creators Using AI Tools: 33:06 – 34:04
• Jill Creating Her Own LLM: 34:15 – 35:47
• Final Words & Listener Advice: 35:47 – end

Tone & Takeaways

• Tone: Conversational, candid, occasionally humorous, pragmatic, and optimistic yet realistic about AI’s challenges.
• Key Takeaways:
  • The AI transition is real and accelerating, but careers are not doomed—curiosity, adaptability, and skill development are your best defense.
  • Leveraging AI tools (for resumes, workflows, etc.) is now essential, not optional.
  • Democratized platforms like Pelgo aim to make career assistance accessible to all, not just executives.
  • Most fulfilling and secure jobs will remain those grounded in human judgment, empathy, and adaptability.

Summary For Listeners

For anyone worried about AI upending their career, this episode offers grounded advice and hope. Embrace change by experimenting with AI tools, focus on what makes you uniquely human, and prepare for more frequent transitions. Platforms like Pelgo are being built to hold your hand through uncertainty—and the show’s own story is a perfect case study in adapting, learning, and not being left behind by technological waves.