The people you’ll actually be talking to
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Stephen Blair
President
Steve is who clients call when there isn't an obvious answer: a coverage problem nobody can untangle, costs climbing faster than the business can carry, a difficult situation with an employee, or something they've already been told can't be done. Most of his week is spent helping business owners make decisions about their benefits they can live with all year rather than just sign off on today, and finding a way forward when something gets complicated.
More than twenty-five years at Lyceum.
Outside work he sits on the boards of the Mental Health Association of Frederick County, the Boys & Girls Club of Frederick County, Leadership Maryland and the Upcounty Chamber Community Foundation. You’ll find him at a baseball or hockey game or out walking his dogs.
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Ryan Cooley
COO
Ryan runs the sales and client service teams, the people you deal with day to day. When a client needs something sorted out, making sure it actually gets sorted is his job.
Two years at Lyceum. Before that, he was a financial advisor.
Outside work Ryan sits on the board of the Boys & Girls Club of Frederick County. He can also be found sideline at one of his kids' activities, out fishing, or watching the Capitals.
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Mackenzie Blair
Vice President
Mackenzie Blair provides ongoing support and personalized service to client groups throughout the plan year. With four years at Lyceum, she helps clients navigate renewals, employee transactions, plan changes, and day-to-day insurance needs, while coordinating with internal teams and carrier partners to resolve issues efficiently.
Mackenzie is committed to making the insurance process as seamless as possible and ensuring each group has a positive experience.
Outside of work, she enjoys spending time with her family and cats.
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Laura Bianchini Pritchett
Vice President, Commercial Lines
Laura Bianchini Pritchett is a dedicated insurance and risk management professional with a passion for helping individuals, families, and businesses protect what matters most. With experience in client relations, insurance solutions, and business development, Laura is known for her commitment to providing personalized service and building long-term relationships based on trust and integrity.
Throughout her career, Laura has worked closely with clients to identify coverage needs, navigate complex insurance options, and develop customized risk management strategies. Her consultative approach and attention to detail have helped clients make informed decisions that support both their personal and professional goals.
Laura is recognized for her responsiveness, professionalism, and ability to simplify complicated insurance concepts into clear, practical solutions. Whether helping individuals, families, or businesses, she focuses on delivering exceptional customer experiences and peace of mind.
Outside of her professional endeavors, Laura values community involvement, continuous learning, and spending time with family and friends. She believes that strong relationships and a genuine commitment to helping others are the foundation of both personal and professional success.
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Amy O'Rear
Commercial Lines Manager
With 36 years of experience as an insurance agent, Amy brings the knowledge, perspective, and personal approach that comes from decades of helping business owners protect what they've worked so hard to build. She believes good relationships start with listening, understanding what matters to each client, and being someone they know they can turn to for honest answers and thoughtful guidance.
Whether it's finding the right coverage, working through an unexpected challenge, answering a question or simply talking through a decision, Amy takes pride in being accessible, approachable, and genuinely invested in her clients. She knows insurance is about much more than policies and paperwork. It's about people, relationships, and having someone in your corner when it matters most.
Amy joined Lyceum Insurance in 2025, and continues to build those relationships and helping clients navigate the ever-changing world of insurance.
Away from work, Amy enjoys spending time with her family and friends, trying the newest restaurant, catching a live concert, or being anywhere near the water. She's just as happy relaxing at home on the couch with her 100-pound chocolate Lab, who believes he is the smallest lap dog.
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Caitlin Herman
Administrative Operations Specialist
For the past 2 years, I have supported our groups throughout the year with enrollment and eligibility changes, helping to resolve discrepancies and coverage issues, and working directly with carriers to find solutions when questions or issues arise. I serve as a resource for both our clients and their employees, helping ensure that enrollment and eligibility matters are handled accurately and efficiently.
Outside of work, I enjoy spending time with my family or watching my favorite comfort show.
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Diana Astacio
Account Manager
Diana supports our benefits groups throughout the renewal process and serves as a resource for clients' day-to-day needs. From answering questions about coverage and plan changes to coordinating processing and deadlines, she helps ensure clients have the guidance and support they need. She also works closely with our Property & Casualty team, providing support and assistance whenever needed to help ensure their clients' needs are met.
With 13 years of experience in the insurance industry, including one year with Lyceum, Diana brings a knowledgeable and client-focused approach to her work. She is fluent in Spanish and enjoys helping clients communicate in whichever language is most comfortable for them.
Diana is a lifelong Marylander who loves being close to the water and in the warm weather. She enjoys spending quality time with her loved ones and her two dogs. She's also a true food enthusiast who loves exploring new restaurants and trying different cuisines.
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Jennifer Freedman
Director of Agency Systems
Jennifer is the one who speaks computer. Every system Lyceum runs on is hers: the applications, the database, Employee Navigator. When something needs to work differently for your group, she’s the person who makes it happen. She likes the problems that don't have an obvious route through, and she'll usually find one.
She's been here ten years. Before insurance she spent her career in nonprofits, first as a fundraiser and later as a comptroller running finance, HR and payroll so when a nonprofit director starts describing their week, Jennifer has had that week. She knows what it's like on the other side of the desk.
Outside work she owns close to 150 bottles of nail polish and has used nearly all of them.
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Kellie Ketron
Client Success Coordinator/Marketing
Kellie is who you call when a claim goes sideways. She investigates what actually happened, chases the answers down, and tells you plainly where things stand rather than leaving you to guess.
She also designs and builds everything else you see from us: this site, our social accounts, and Frederick Friday.
Just over a year at Lyceum, and ten years before that in Frederick’s handmade and local arts world. The local part of this job isn’t new to her.
Outside work she’s usually at a live show, an art gallery, in her own sewing studio or hanging out with friends. She studied Music Business and made it to the Grammys once as a guest!