Jason Randall
Up In Your Business
Up In Your Business with Jason Randall is a podcast for business leaders navigating the real challenges of running and growing a company. Each episode dives into the issues that matter most to employers today—from HR and compliance to benefits, leadership, culture, and day-to-day operational decisions. The goal is simple: give you clear, practical insight you can actually use. Hosted by Jason Randall, the show brings straightforward conversations, real-world perspectives, and expert guidance to help you make smarter decisions for your business and your people. Whether you're scaling your team,...
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Episodes
What Should Business Leaders Actually Know About AI Right Now? (#5) 08.07.2026 28:39
In this episode of Up In Your Business, I sit down with Chris Whitney, our technology leader at Questco, to explore the transformative role of AI in the workplace. We discuss how AI can streamline operations, enhance productivity, and empower teams without the fluff often found in tech conversations. Chris shares a compelling real-world case study involving the development of an AI-driven chatbot...
The Real Signs It’s Time to Seek Outside HR Support (#4) 01.07.2026 28:24
In this episode of Up In Your Business, Jason Randall and Sierra Silverberg to explore a critical question for business leaders: When is it time to seek outside help for HR? They discuss the signs that indicate your current HR setup might not be sustainable, such as leadership distraction, high employee turnover, and inconsistent policies. Sierra shares insights on how to recognize the tipping poi...
What Happens If You Fire Someone the Wrong Way? (#3) 24.06.2026 27:13
In this episode of Up In Your Business, Jason and Santos delve into the complexities of terminating employees and the potential pitfalls of doing it the wrong way. Firing someone is one of the toughest tasks a leader faces, and mishandling it can lead to legal battles and business disruptions. Joined by Santos Alvarenga, a seasoned HR consultant, we explore the importance of proper documentation,...
Do You Really Need HR Support, or Are You Fine Without It? (#2) 17.06.2026 27:58
In this episode of Up In Your Business, I dive into a crucial question for growing companies: Do you really need HR support, or can you manage without it? As businesses expand, the complexities of HR can quickly become overwhelming. I discuss the tipping point when informal HR practices begin to falter and the risks that arise when organizations lack structured support. Joining me is Jason Millman...
What HR Mistakes Can Actually Get Your Company Sued? (#1) 10.06.2026 32:59
HR risk usually starts earlier than most business leaders think. In this episode of Up In Your Business, host Jason Randall sits down with Christy Arnold, General Counsel and SVP at Questco, to talk about the HR mistakes that can create real legal, financial, and operational risk for employers. The conversation covers misclassification, hiring technology, documentation, terminations, inconsistent...
Episode 1 Teaser: Coming Soon 03.06.2026 1:57
In this first episode of *Up In Your Business*, host Jason Randall, Chief Growth Officer at Questco, is joined by Christy Arnold, Questco’s General Counsel and SVP, to discuss the HR mistakes that often seem small in the moment but can create serious liability for businesses. Together, they explore how issues like employee misclassification, inconsistent people practices, missing documentation, an...
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