With over 100 years of combined experience, we are committed to delivering a white-glove experience—marked by attentiveness, responsiveness, and effectiveness—from initial onboarding through the ongoing management of your benefits program. This includes funding strategies, plan performance optimization, compliance oversight, and employee communications. We pride ourselves on using the latest tech stacks available to position the client in a successful and streamlined experience.
We believe in leading with courage and integrity, regardless of the outcome. This philosophical ethos is the heart of our firm. For us, value creation is not just a metric—it’s a mission. Our word is our bond, and that bond forms the foundation of every partnership we build. Many of our client relationships evolve into personal meaningful friendships, which we deeply cherish.
Trust is earned, not given—and we welcome the opportunity to earn yours.
Steven P. Kelly
Managing Member and Co-Founder
Kelly and Calloway Insurance Group
Managing Partner, Kelly and Calloway Insurance Group
Steven is a Boston native with a deep-rooted desire to see those around him thrive. Steven brings heart, grit, and vision to everything he does.
After spending 13 years on Wall Street, his career took a meaningful turn toward the employee benefits and property and casualty insurance space, where he found purpose in helping organizations build healthier, happier workplaces. He holds board positions with numerous private companies and has been recognized with multiple awards, including the Phoenix Business Journal’s “Innovator of the Year” honor for his leadership in developing COVID-19 solutions for Arizona businesses and communities.
As Managing Partner of Kelly and Calloway Insurance Group, Steven leads with thoughtfulness, transparency, and unwavering availability. He believes that true client partnerships are built on human-to-human connection—not just transactions. That means educating clients on insurance and technology, listening deeply, and always focusing on value creation.
Steven is a graduate of Thomas More College of Liberal Arts where he majored in Political Science. His love for the engagement of discourse and people comes across on the way he approaches complex issues for clients.
Outside of work, Steven is an avid golfer, playing courses across the country whenever he gets the chance. Life is full and lively with his wife and four children, whose schedules are packed with sports and activities. He’s also deeply involved in community events and philanthropic ventures, always looking for ways to give back and make a positive impact beyond the office
Managing Partner, Kelly and Calloway Insurance Group
Ryan Calloway is an Indiana native, a managing partner with Kelly and Calloway Insurance Group, and has over eight years of experience designing tailored group benefits solutions for companies ranging from agile startups to established mid-size firms.
With a sharp eye on market trends and a deep understanding of the health insurance landscape, Ryan specializes in crafting benefits strategies that balance employer cost goals with meaningful employee value.
His approach is both analytical and human-centered—merging data-driven insights with a personal touch to deliver plans that are financially sound and genuinely supportive of workforce wellbeing. From navigating compliance to optimizing plan design, Ryan helps employers cut through complexity and make confident, informed decisions.
Before entering the insurance world, Ryan earned his degree in Logistics and Supply Chain Management from Ball State University, equipping him with a strong foundation in operational efficiency, strategic planning, and systems thinking. He also brings consulting experience from the pharmaceutical and entertainment industries, where he led multifaceted projects requiring creative problem-solving and cross-functional collaboration.
Outside of work, Ryan is a passionate traveler who loves discovering new cities, coffee spots, and culinary gems. He’s also a fan of mentally engaging games like poker and chess, which reflect his love for strategy, patience, and smart decision-making.
Managing Partner, KCT Medwise Insurance Agency
Jessica is an Arizona native with a deep passion for helping people feel informed, empowered, and confident when navigating their benefits.
With over a decade of experience in Human Resources, Medicare, and group benefits, she brings both strategic insight and personal care to every client interaction.
A proud graduate of the University of Arizona, Jessica holds a Bachelor of Science in Psychology and Sociology. Her academic foundation, paired with hands-on industry experience, allows her to translate complex benefits information into clear, relatable guidance for individuals and organizations alike.
Jessica is widely recognized for her approachable style, clear communication, and unwavering commitment to supporting clients through every stage of the enrollment process—and beyond. She thrives on building genuine relationships and crafting solutions that make a meaningful impact.
Outside of work, Jessica is a proud mom of three, a devoted animal lover, and an unapologetic Harry Potter enthusiast. She enjoys soaking up the Arizona sunshine and believes that a great day includes good company, a little magic, and a cold iced coffee.
Managing Partner, KCP Property and Casualty Advisors
Erik has built strong property and casualty expertise through hands-on client work, continuous industry learning, and consistent application of coverage knowledge to real-world insurance situations
Erik’s attentiveness and creative approach to client needs allow him to proactively identify exposures, design strategic coverage solutions, and help individuals and businesses effectively mitigate risk in an ever-changing landscape.
Erik is a proud graduate of Illinois Central College, where he earned a bachelor’s degree in business, building a strong foundation that continues to shape his professional values and client-focused approach today.
Outside the office, Erik has a 3-year-old daughter and enjoys staying active and spending time on the golf course. He is passionate about his work and places a strong emphasis on building lasting relationships, valuing trust and connection both professionally and personally.
