Episode 4: Understanding the Challenges of Small Business Owners

Episode 4: Understanding the Challenges of Small Business Owners

What keeps employees around long term? In Episode 4 of Your Friends with Benefits podcast, Decisely host Chris Covill sits down with entrepreneur and business owner Will Boyd shares what it really takes to build and retain a strong workforce. From navigating the unexpected challenges of insurance to creating a people-first culture with meaningful employee benefits, Will reflects on the lessons he’s learned growing two businesses and leading nearly 200 employees. This conversation offers practical insight for small business owners looking to build teams that stay, grow, and thrive.

Episode 3: What Employers Need to Know About Benefits Regulatory Compliance Obligations

In this episode of Your Friends with Benefits, Chris Covill sits down with Decisely’s VP of Regulatory Compliance, Elizabeth Collins, to break down one of the most overlooked—and high-risk—areas of employee benefits: compliance. From federal regulations like ACA, ERISA, HIPAA, and COBRA to varying state-level requirements, employers face a complex web of rules when sponsoring health coverage. Chris and Elizabeth unpack what compliance actually means, why it matters, and how it impacts businesses of all sizes—whether you’re offering traditional group plans or exploring options like ICHRA. They also dive into the real risks of getting it wrong—from costly penalties and lawsuits to damaged employee trust—and explain how employers can stay ahead of evolving requirements. If you’ve ever wondered what your responsibilities are (and how to avoid compliance headaches), this episode is a must-listen.

Episode 2: Group Health vs. ICHRA - What Options Do Employers Really Have?

In this episode, Chris Covill is joined by Decisely leaders Fred Langenfeld and Jess Southwell to break down the different ways employers can offer health benefits to their teams. From traditional group health insurance options such as fully insured, level-funded, and self-insured plans, to the rapidly growing Individual Coverage Health Reimbursement Arrangement (ICHRA), employers today have more choices than ever when it comes to designing a benefits strategy. Fred and Jess walk through how these options work, what’s driving the rise of ICHRA, and how employers can evaluate which approach best fits their workforce, budget, and long-term goals. They also discuss how today’s diverse workforce is influencing benefit decisions and why flexibility and choice are becoming increasingly important. If you’re an employer trying to navigate the evolving healthcare landscape, this episode will help clarify the options available and how to make more informed benefits decisions.

Episode 1: Do Employee Benefits Matter?

Welcome to the inaugural episode of Demystifying Employee Benefits, hosted by Chris Covill, Chief Growth Officer at Decisely. In this first episode, Chris is joined by Wyatt Bailey, who leads Decisely’s Business Intelligence, Data & Analytics team, and Linh Muir, Head of Marketing at Decisely, to unpack a critical question: Do employee benefits really impact retention? Each year, Decisely conducts a deep analysis of employer client data to better understand how medical benefits influence employee tenure. The findings are compelling. Across multiple high-turnover industries—including logistics, hospitality, quick service restaurants, and automotive—employees with access to medical benefits stayed more than twice as long as those without. In this episode, the team discusses: - How the analysis was conducted and what makes it statistically meaningful - The measurable connection between medical benefits and employee tenure - Why retention is a bottom-line business issue, not just an HR initiative - The financial impact of turnover and workforce instability - How benefits strategy can drive long-term business outcomes This isn’t theoretical. It’s based on real client data and real workforce outcomes. If you’re an employer navigating rising healthcare costs, retention challenges, or operational instability, this episode offers data-backed insight into why benefits matter more than ever. To access the full Benefits Matter report, visit: https://decisely.com/white-paper-benefits-that-drive-business-success/