Jonathan Baily enjoys working directly with people and making a meaningful impact in their lives and businesses. Whether he’s helping employers manage their costs, attract top talent, or reduce turnover, Jonathan enjoys serving as a trusted advisor and helping others navigate the complex world of group benefits.

Having been around the insurance industry for much of his life, Jonathan brings a unique blend of industry familiarity, analytical thinking, and relationship-focused service to his role at Baily Insurance. Before stepping into employee benefits production, he gained experience in a variety of areas including property & casualty insurance, accounting support, sales support, marketing, and data analysis. These experiences gave Jonathan a strong appreciation for both the analytical side of the business and the personal relationships that are at the heart of serving clients well.

Today, Jonathan works directly with employers to tailor and optimize employee benefits packages that best fit the needs of both the company and its employees. He enjoys helping clients evaluate their options, solve challenges, and build benefits programs that support employee wellbeing while aligning with business goals. Jonathan takes pride in being accessible, dependable, and proactive in serving his clients.

Outside of work, Jonathan enjoys staying active and spending time with the people closest to him. He and his wife, Hannah, stay busy with their daughters, Kayla and Tessa, and they often enjoy swimming, card games, and family movie nights together. Jonathan is also passionate about fitness, music, and sports. He’s a diehard fan of the Pittsburgh Steelers — and rarely misses a game!