Inside Job: Why We’re Listening First in the Age of AI and Uncertain Work

A college student takes a $50-an-hour job training artificial intelligence and ends up making $70,000 in a single year. But behind the money is a hidden world of digital labor, where real people shape how AI thinks, responds, and sounds—and where the work is already starting to disappear. In this episode of Inside Job, host Matt Sunbulli profiles Isaiah, a college-age AI trainer, and together they take listeners inside a hidden layer of the tech economy. What they uncover reveals the human force behind AI—and raises urgent questions about where this work is headed and what it means for all of us.

Inside Job host and creator Matt Sunbulli and executive producer Aaron Calafato set the stage for the new series, preview upcoming stories, and explain why starting with listening first and honoring the real experiences of job seekers and workers matters more than ever as AI reshapes the future of work. In doing so, they show what sets this podcast apart from others in the career space today. *If you have a story to share, an episode idea or want to join our community visit: insidejobpodcast.com

Hosted by Matt Sunbulli and executive produced by Aaron Calafato, this pilot episode of the Inside Job Podcast pulls back the curtain on one of the fastest-growing and least understood roles in the economy: AI data work. We hear from Krista, a longtime data worker in Michigan, whose job is to quietly shape the intelligence behind the tools millions of people use every day. “I’m teaching AI how to talk… how to see… how to think.” But behind the promise of AI is something far more human: A living room turned into a workplace A constant search for tasks and income Ethical dilemmas about the work itself The isolation that comes with invisible labor What sounds like cutting-edge technology is, in reality, a marketplace of clicks, decisions, and human judgment. This episode introduces a new kind of storytelling about work, inspired by Working by Studs Terkel, capturing not just how people make a living, but how they make sense of it. Because behind every “intelligent” system…there’s still a person.

The team digs through the archives of The Lonely Office and notices a pattern: even as work keeps changing, human nature doesn’t. From AI-driven layoffs to the strange new reality of job searching, Aaron, Matt, Leah, and Ken revisit some of the show’s most revealing conversations about meaning, work, and what might come next. Important Note from the TLO team: Hey TLO listeners, for those who enjoyed our bonus series Ask a Recruiter, that conversation is still going. This spring, find AAR live on Glassdoor's LinkedIn and YouTube, where hiring managers, career coaches, and talent leaders give you real talk on the job market - and ask your questions in real time. To be notified, follow us on LinkedIn: ⁠www.linkedin.com/company/glassdoor Also, 50 years working at a 7/11, bro gets an email

“Follow your passion” sounds great until you are burned out, laid off, or stuck in the same role for years. In this Ask a Recruiter bonus episode, Leah Ova sits down with career coach and Finding Brave host Kathy Caprino to unpack what is missing when vision boards and inspirational quotes stop working. They break down the bravery and power gaps that keep people stuck, plus practical moves to get clear, get visible, and make a realistic career pivot in today’s job market. Important Note from the TLO team: Hey TLO listeners, this will be the last Ask a Recruiter episode you’ll hear as part of this show. The AAR conversation isn't ending -  it's just getting started. This spring, find AAR live on LinkedIn and YouTube, where hiring managers, career coaches, and talent leaders give you real talk on the job market - and ask your questions in real time. To be notified, follow us on Linkedin: www.linkedin.com/company/glassdoor

Interviews are not just about what you know. They are about how you think on your feet, respond under pressure, and show up with confidence when you do not have a perfect script. In this episode of Ask a Recruiter, Leah Ova sits down with improv coach and communication expert Holly Mandel to explore how improv techniques like “yes, and,” presence, and active listening can transform your job interview performance. Holly Mandel is the founder of iMergence and a former Main Company member and instructor at The Groundlings. She works with professionals and Fortune 500 teams to build confidence, clarity, and real time communication skills that translate directly into high stakes conversations. Together, Leah and Holly tackle tough interview questions from the Glassdoor community, from “Tell me about yourself” to curveballs like “How would you sell ice cream in the Arctic?” They break down practical tools you can use immediately, including how to pivot mid answer, manage interview anxiety, project warmth and energy on Zoom, and build the kind of charisma that gets you to the next round. If you are job hunting, preparing for a promotion, or simply want to communicate with more authority and authenticity, this episode gives you actionable strategies you can try this week.

Are you embarrassed to work for your company? In this episode of The Lonely Office, we revisit a story about loud quitting, corporate misalignment, and the tension between survival and integrity in today’s workplace. As ESG debates, layoffs, and corporate reputation shape the 2026 work landscape, we explore how employees decide where their moral line is — and what it means when a job starts to feel like a liability. Hosts: Matt Sunbulli ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.linkedin.com/in/sunbulli/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.firstdraft.vc⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Aaron Calafato ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Listen to Aaron's 7 Minute Stories Podcast ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Leah Ova ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Follow Leah on TikTok ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Editorial: Matt Sunbulli Brooks Borden Ken Wendt Senior Audio Engineer: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Ken Wendt ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Research: Matt Sunbulli Zaid Safe Aaron Calafato

Why does workplace satire hit so hard? And why does corporate language feel… strangely terrifying? In this episode of The Lonely Office, we talk with Henry Marken, Director of Social Media/Content Creator at Wunderfan and viral creator known for blending sports fandom, comedy, and office culture. We unpack how corporate culture trains people to wear masks, and why comedy becomes a kind of survival mechanism. Along the way, we explore what sports pain teaches us about work, how AI is reshaping careers, and why authenticity feels harder inside big organizations. Special Guest: Henry Marken Hosts: Matt Sunbulli ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.linkedin.com/in/sunbulli/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.firstdraft.vc⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Aaron Calafato ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Listen to Aaron's 7 Minute Stories Podcast ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Leah Ova ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Follow Leah on TikTok ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Editorial: Matt Sunbulli Brooks Borden Ken Wendt Senior Audio Engineer: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Ken Wendt ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Research: Matt Sunbulli Zaid Safe Aaron Calafato

Why does applying online feel so frustrating even when the data says it works? The TLO team team talk with career strategist Madeline Mann again. This time about why most applications get buried, how referrals and sourcing really drive hiring, and what job seekers can do to cut the line and get noticed. Special Guest: Madeline Mann Hosts: Matt Sunbulli ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.linkedin.com/in/sunbulli/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.firstdraft.vc⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Aaron Calafato ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Listen to Aaron's 7 Minute Stories Podcast ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Leah Ova ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Follow Leah on TikTok ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Editorial: Matt Sunbulli Brooks Borden Ken Wendt Senior Audio Engineer: ⁠⁠⁠⁠⁠⁠⁠⁠⁠Ken Wendt ⁠⁠⁠⁠⁠⁠⁠⁠⁠ Research: Matt Sunbulli Zaid Safe Aaron Calafato