Jeremy Schifeling: Kindergarten Teacher to Founder of The Job Insiders

In this episode of Clocking Out, we sit down with Jeremy Schifeling, founder of The Job Insiders and author of the Amazon best-seller LinkedIn and ChatGPT for Job-Seeking.

Growing up in the working-class city of Buffalo and dreaming of playing for the Chicago Cubs, Jeremy learned early on how to hustle, adapt, and punch above his weight. Jeremy shares how his early days substitute teaching in Brooklyn classrooms—often a trial by fire—helped him discover his true passion: empowering others through technology and education. That small spark led him to roles impacting hundreds of thousands of learners and building new skills in marketing, research, and strategy.

But breaking into top tech companies wasn’t about perfect grades or a shiny resume — it was about building trust, finding insiders, and getting in through the side door. Jeremy shares how real relationships—not brand names—were the secret to unlocking the next stage of his career.

Eventually, he realized he wanted more than just a seat at someone else’s table. He wanted to build his own. So he stepped away from big tech to launch The Job Insiders, helping others find fulfilling work by rewriting the rules of job searching.This episode is packed with hard-won wisdom on how to find the right career path, navigating career pivots, and using your unique story as your greatest advantage.

Connect with Jeremy at:
LinkedIn: https://www.linkedin.com/in/schifeling/
Instagram: https://www.instagram.com/jobinsiders/
X: https://twitter.com/2LinkedInGuys
Website: https://www.thejobinsiders.com/
LinkedIn and ChatGPT for Job-Seeking: https://www.amazon.com/Career-Coach-GPT-Complete-Interview/dp/B0C8QRMCFC

Follow Raymond:
LinkedIn: https://www.linkedin.com/in/raymondmlee/
Instagram: https://www.instagram.com/raymondlee.co
Tiktok: https://www.tiktok.com/@clockingoutpod
X: http://twitter.com/hrentrepreneur
Youtube: https://www.youtube.com/@clockingoutwithraymondlee/videos

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