Up In Your Business

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, managing change, or trying to stay ahead of what’s next, this podcast is built for you.

Episodes

Why Organizational Culture Is a Strategic Driver of Business Growth (#9)

August 5, 2026 • 24 mins
In this episode of Up In Your Business, we delve into why organizational culture is a strategic driver of business growth. I, Jason Randall, your host and Chief Growth Officer at Questco, am joined by Kim Diorio, Questco's Chief Product Officer, to explore the tangible impact of culture on enterprise value. We discuss how culture transcends perks and platitudes, becoming a system of decision-making that influences business durabili...
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Customer Experience as a Growth Strategy: The Hidden Profit Signal Business Leaders Can't Ignore (#8)

July 29, 2026 • 33 mins
In this episode of Up In Your Business, I delve into the critical role of customer experience as a growth strategy, revealing it as a hidden profit signal that business leaders can't afford to ignore. Joined by Questco's Chief Product Officer, Kim Diorio, we explore how customer experience is more than just a satisfaction score—it's a comprehensive journey that impacts retention, pricing power, and overall business value. We ...
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Why Clarity Breaks First in Rapid Business Growth (#7)

July 22, 2026 • 32 mins
In this episode of Up In Your Business, I dive into the crucial topic of clarity in fast-growing businesses. Joined by Kim Diorio, Questco's Chief Product Officer, we explore why clarity often breaks first as companies expand. Many assume operations or hiring falter first, but we argue that losing a shared understanding of goals and priorities is the real culprit. We introduce the "Three Cs" framework: Clarity, Customer Experience,...
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What Does a PEO Actually Do and Do You Need One? (#6)

July 15, 2026 • 32 mins
In this episode of Up In Your Business, Jason Randall, Chief Growth Officer at Questco, dives into the world of Professional Employer Organizations (PEOs) with Brandon Hartsough, COO of Questco. They demystify what a PEO actually does and explore whether your business needs one. Brandon shares his extensive experience in the PEO industry, explaining how PEOs relieve businesses of administrative burdens, allowing them to focus on gr...
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What Should Business Leaders Actually Know About AI Right Now? (#5)

July 8, 2026 • 28 mins
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 named Beth, which drastically reduc...
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The Real Signs It’s Time to Seek Outside HR Support (#4)

July 1, 2026 • 28 mins
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 point, the common mistakes leaders mak...
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What Happens If You Fire Someone the Wrong Way? (#3)

June 24, 2026 • 27 mins
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, consistent communication, and clear...
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Do You Really Need HR Support, or Are You Fine Without It? (#2)

June 17, 2026 • 27 mins
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, an expert who shares insights on ...
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What HR Mistakes Can Actually Get Your Company Sued? (#1)

June 10, 2026 • 32 mins
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 policies, and manager training....
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Episode 1 Teaser: Coming Soon

June 3, 2026 • 1 min
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, and rushed terminations can qui...
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