What if the best thing you can do early in your career is stop trying to get everything right?
In this episode of *Chat the Chief*, Insight Global CEO Bert Bean is joined by Steve Wasik, Vice President of Technology Solutions, and Katie Hillary, Vice President of Strategic Accounts, to talk about what it really takes to build a successful career — especially when you’re just getting started.
From taking risks and finding the right mentors to navigating failure and figuring out what you’re actually good at, Bert, Steve, and Katie share the advice they wish they had at 22.
They dive into:
* Why getting reps early in your career can matter more than getting everything perfect
* Why work ethic and adaptability can take you further than talent alone
* How taking risks helps you figure out what you’re good at — and what you actually enjoy
* Why the people you work for and with can matter just as much as the job itself
* How to seek out mentors, relationships, and opportunities instead of waiting for them to find you
* Why AI could make communication, creativity, relationships, and other “intangible” skills even more valuable
* The career advice they’d give anyone walking into their first day of work
Their biggest advice? Put yourself out there. Take the risk. Ask the question. Get the reps. You’re going to learn either way.
About the Podcast:
*Chat the Chief* is your microdose of leadership and culture — straight from a CEO navigating one of the fastest-changing markets today. Bert Bean became CEO of Insight Global after starting as an entry-level recruiter over 20 years ago. Now he’s giving listeners an unfiltered look into decision-making, purpose, resilience, and modern leadership. Alongside Technology Solutions expert Steve Wasik and Strategic Accounts VP Katie Hillary, this trio explores the principles that make teams thrive and companies grow.
About the Hosts:
Bert Bean is the Chief Executive Officer of Insight Global, one of the world’s leading talent, consulting, and AI companies. He joined the company in 2005 as an entry-level recruiter and became CEO thirteen years later. Under his leadership, Insight Global has more than doubled revenue — from $1.9 billion in 2017 to $4.8 billion in 2025 — and grown to 5,500 employees and 33,000 consultants worldwide.
Steve Wasik is VP of Technology Solutions for Insight Global’s Consulting division, where he partners with IG Labs, the company’s AI services and software practice, to bring scalable enterprise agentic solutions to customers across the world.
Katie Hillary is a sales veteran of Insight Global and now oversees the company’s Strategic Accounts division. A former standout sales executive, she specializes in building systems that accelerate development, growth, and long-term success for some of IG’s largest strategic partners.
📩 Have a question for Bert? Send it to [chatthechief@insightglobal.com](mailto:chatthechief@insightglobal.com) — it might be featured in the next episode!