Matthew Naylor interviews Joe Hessling, CFO of Parcels, about his career in finance and the challenges of managing healthcare costs for a growing, people-focused business. Joe shares how years in the fully insured market led to frustration with rising costs, lack of transparency, and limited control over decision-making.

He explains how transitioning to a level-funded model and eventually into a captive provided greater visibility, predictability, and access to data, allowing Parcels to better manage risk and support employees. For the first time in years, the company was able to maintain stable costs without shifting the burden to employees.

Joe emphasizes that the biggest impact has been improved transparency, stronger partnerships, and a more proactive approach to healthcare management, giving him confidence in long-term planning and a better overall experience for both the company and its employees.

Matthew Naylor interviews Ryan Hanratty of Swingle Collins, who shares how his path from professional golf into employee benefits shaped his work ethic and approach to business. He explains how resilience, discipline, and learning from failure translated directly into building and growing a successful benefits practice.

Ryan discusses how his firm focuses on educating employers about alternatives to traditional healthcare models, using data-driven strategies and creative solutions to reduce costs and improve outcomes. He emphasizes the importance of personalized approaches, especially in areas like pharmacy benefits, where better sourcing and awareness can significantly impact both employers and employees.

He also highlights the importance of culture and leadership, describing a family-oriented company environment and a philosophy centered on putting others first. For Ryan, long-term success in both business and life comes from serving others, continuously improving, and staying committed to making a meaningful impact.

Matthew Naylor interviews Don Gasparro, who shares his journey from aspiring teacher to actuary and eventually to building and scaling a major stop loss insurance business. After early roles at Aetna and in consulting, Don co-founded Apex Management Group, which grew through its data-driven approach before being acquired by Gallagher. Don explains how thinking creatively, developing new structures like captives, and solving real employer problems helped reshape the market.

The conversation also explores the future of captives, emphasizing that success depends less on the financial vehicle itself and more on actively managing risk, educating employers, and aligning incentives. Don highlights that the next phase of the industry will be driven by organizations that combine deep expertise with integrated solutions to truly control costs and improve outcomes.

Matthew Naylor interviews Jeramie Holt, director of employee benefits at FNIC, about his path from car sales into the insurance world and how he helped build FNIC’s presence in Colorado. Jeramie shares how his early sales background shaped his approach and why he moved away from traditional brokerage models.

He explains his focus on a more consultative strategy, helping employers think long-term about their benefits instead of relying on simple plan comparisons. The conversation highlights alternative funding strategies, creative plan design, and the importance of educating both employers and employees to drive better outcomes.

Jeramie also emphasizes the value of strong partnerships, transparency, and consistent execution, noting that better support for employees ultimately leads to stronger results for organizations.

Matthew Naylor interviews Judy Young, who leads the employee benefits department at Dean and Draper, about her journey into the insurance and benefits space and the evolving challenges within healthcare. Judy shares how she worked her way up from administrative roles into brokerage, offering insight into how benefits teams support employers through implementation, employee access, and ongoing plan management.

The conversation highlights the growing complexity and rising costs of healthcare, especially for employers navigating limited flexibility within traditional insurance structures. Judy explains that much of her work focuses on optimizing plan design, educating clients on utilization, and helping employees better access care while managing expenses.

They also explore systemic issues within the healthcare system, including prescription drug costs and inefficiencies tied to pharmacy benefit managers. Judy emphasizes the importance of finding better solutions to make medications more affordable and improve outcomes for both employers and employees.

On this episode of Alignment for Impact, Matthew Naylor sits down with Crumdale Specialty founding partners Jake and Brian to reflect on the journey of building a company rooted in alignment, culture, and long term impact. They share their personal paths into entrepreneurship, from law and finance to insurance and healthcare, and how early relationships, curiosity, and a willingness to ask why shaped Crumdale’s operating philosophy.

The conversation explores how leadership, accountability, and trust became the foundation for a people first culture, including the now famous Crumdale Code and its emphasis on integrity and respect. Jake and Brian walk through how Crumdale approached innovation differently by integrating risk financing, healthcare services, cost containment, and technology into a single aligned platform. At its core, this episode is about building something meaningful by putting people first, embracing transparency, and proving that when alignment exists across the ecosystem, everyone can win together.

On this episode of Alignment for Impact, host Matthew Naylor sits down with Kelly Brady to explore what it really means to move from transactional insurance brokerage to true healthcare consulting. Kelly shares his path from Wisconsin into the employee benefits space, the mentors who shaped his approach, and how his role has evolved into one focused on partnership, education, and long term impact for employers and employees alike.

The conversation breaks down the unique dynamics of the Midwest healthcare market, the rise of level funded plans, and the challenges employers face when pharmacy costs spiral out of control. Kelly walks through a real client case where Crumdale Specialty helped intervene on high cost specialty drugs in a way that protected both the employer and the employee experience. At its core, this episode is about alignment, transparency, and empowering employers and employees to become better consumers of healthcare without fear or disruption.

On this episode of Alignment for Impact, host Matthew Naylor sits down with Jim Andrews to unpack a career shaped by grit, loyalty, and an athlete’s mindset. Jim traces his journey from growing up in Philadelphia to competing and coaching at the Division I level, then navigating a winding professional path that took him from coaching and hospitality into sales leadership at high-growth tech companies. Along the way, he reflects on lessons learned from mentors, failures that forced growth, and the discipline required to lead teams through uncertainty.

The conversation dives deep into Jim’s transition into healthcare entrepreneurship and the early days of building Crumdale Specialty from the ground up. He shares what it takes to create a people-first culture, why standards matter more than titles, and how trust, autonomy, and shared values can fuel rapid growth. At its core, this episode is about leadership, alignment, and building something meaningful without losing sight of family, character, and purpose.