Who We Are

CEO | Managing Partner

Quinn Shepherd

Quinn Shepherd is the Chief Executive Officer and Managing Partner. He is dedicated to leading and serving the organization’s esteemed team. Quinn oversees 45+ offices, 650+ employees, 64 equity partners, and the Board of Directors. His role also involves spearheading mergers and acquisitions. As a 43-year-old Independent CEO leading a $100M revenue company, Quinn is entrusted with the well-being and success of individuals spanning five different generations. 

Prior to joining Shepherd Insurance, he was a sales advisor for Universal Underwriters, a division of Zurich Insurance. Quinn graduated from Ball State University in 2004, where he has since received the 2013 G.O.L.D.(Graduate of the Last Decade) award and was honored to be presented with the 2017 David Letterman College of Communication Information Media (CCIM) distinguished alumni award. In 2023, Quinn was elected to the Ball State University Sigma Phi Epsilon Hall of Fame. As part of his commitment to Ball State University, he was a past chairman of the BSU College of Risk Management and Insurance (RMI) Advisory Board and is an active member of the Dean’s Advisory Board for the College of Communication Information and Media (CCIM).  

Quinn actively contributes to multiple boards, including Booth Tarkington Civic Theatre Board of Directors, Indianapolis 100 Club, Central Indiana Police Foundation, Circle City Relief, and Wisdom and Grace Ministries. He was also a previous board member of the Center for Performing Arts, Westfield Insurance, and Martin Riverside Society. 

Beyond his professional accomplishments, Quinn was inducted into the Carmel High School Hall of Fame in 2022 and founded Operation Shepherding, Shepherd Insurance’s national outreach program. Quinn is a devoted husband to his wife, Ali, and a loving father to his four children. 

Founder | Chairman

Dave Shepherd

David Shepherd founded Shepherd Insurance in 1977 to provide personal insurance and top-notch service to friends and neighbors. He started the business with zero clients and is now one of the Top 50 largest P&C agencies in the country. Almost four decades later, his agency has grown to include employee benefits and financial products.

Dave serves as the Chairman of Shepherd Insurance and gives credit for the agency’s continued success to the amazing team that has been built at Shepherd. Because of them, the company was recognized in 2013-2015 as Top 100 U.S. Agency by Insurance Journal, 2014 Agency of the Year by IIAI (Big “I“), 2014-2015 Top 5000 Fastest Growing Companies by Inc. Magazine, and 2014 Top Ten Independent Agencies in Indiana by Indianapolis Business Journal. Dave was honored by Business Insurance by being inducted into the Hall of Fame in 2018.

Dave is a native Hoosier and a proud Carmel High School alumnus in Carmel, Indiana. He graduated as an All-SEC Academic All-American basketball player from the University of Mississippi. Together with his wife, Sally, he lives in Carmel. When they are not working or playing golf at Crooked Stick, they enjoy hanging out with their seven kids and eleven grandkids.

Lead President | Partner

Jeff Kweder

As President of Shepherd Insurance, Jeff Kweder is responsible for oversight of the agency including key account management, strategic direction, vendor evaluation and mergers and acquisitions. He has over 35 years of service with the agency and is licensed to sell health insurance, casualty insurance. He started the employee benefits division in 1987 and works exclusively with mid-sized to large businesses.

Throughout his career, Jeff has been actively involved in insurance organizations such as the Independent Insurance Agents & Brokers Association (Big “I”), MarshBerry’s APPEX association and is a member of the Agent Editorial Advisory Board for Rough Notes magazine. He graduated with a Business Administration degree from Ohio State University. Jeff resides with his wife, Julie, and their four children in Carmel, Indiana.

Lead COO | VP of Sales | Partner

Pete Harrington

Pete Harrington is a Partner, Chief Operating Officer, and Vice President of Sales, along with being a part of the executive management team.   Pete is a graduate of Butler University and an enthusiast of all Bulldog athletics. He is licensed in both life & health and property & casualty insurance. Pete has current and prior experience serving on the Agency Advisory Councils for Nationwide, Selective, Secura, West Bend and Westfield Insurance companies. He is a graduate of the Kellogg School of Management series of business courses.

He has previously served on the board of directors for the O’Connor House. The O’Connor House Mission is to provide a Christian home to help single, pregnant, homeless women improve life for themselves and their children. 

Though a great deal of his time is spent at the Carmel headquarters, due to Shepherd’s growth, he does often travel nationally between offices. Pete oversees all lines of business managers and leads the direction of all sales agents. Pete helped create and nurture the internship program at Shepherd with an active pipeline coming from Indiana State, Ball State, Butler Universities, as well as Florida State and Eastern Kentucky. Pete also continues to build strong relationships with Shepherd’s key carriers and partner carriers. Pete and his wife Stacey live in Carmel and have both of their daughters (Reiley & Ellie) married, son (Ty) who is a senior at the University of Notre Dame, and granddaughter Mary Rose (3).  

Chief Administration Officer | Partner

Tom Niccum

Tom is an Executive Partner at Shepherd Insurance and the Chief Administration Officer. He oversees marketing, property and casualty carrier relationships, and the education and development of the Shepherd team. Tom is an integral part of the onboarding of new employees and the assimilation of new partnerships into the Shepherd family. An important part of the training and development is Shepherd University, an educational program that helps Shepherd employees continue to learn and grow in the insurance industry. Tom is a part of the executive team and works to continually grow and improve Shepherd Insurance by encouraging a positive culture and helping make internal connections.

A team member since 1999, Tom has held numerous positions within the company, including personal, commercial and truck dealerships. He has completed his CPCU designation and holds degrees in Risk Management & Insurance and Mathematics from Ball State University. He represents the agency on multiple agent advisory councils. Married with three kids, Tom and his family live in Carmel, Indiana. When he gets away from the office, you can find Tom supporting his children at sporting events, hanging out with his friends and family or participating in various outdoor activities at home or at the lake.

COO of the Florida & Arizona Region | Partner

Patrick Del Medico

During his 30+ years of documented success in sales, marketing, training, product development, and performance management, Patrick has spent time in executive leadership roles both nationally and internationally. His diverse expertise and strategic business planning have helped him to consistently improve business processes and create winning teams for large Fortune 500 Companies ranging from Proctor & Gamble, Stryker Corporation and Baxter Healthcare to start-up entities to family-owned businesses.

Patrick oversees the daily operations of the Florida and Arizona region. He provides leadership and strategic management to foster organizational growth, ensure financial strength, and operating efficiency.

Patrick earned his BA in Communications from DePauw University in Greencastle, Indiana. He is extremely active in the local community and dedicates a great deal of his time to both multiple charities and business organizations. His passion is helping children reach their full potential and he has focused much of his volunteer efforts toward supporting causes and organizations like Girls Inc., Girl Scouts, Boys and Girls Club and Cardinal Mooney High School. 

Patrick currently serves on several influential boards, including USF Risk Management & Insurance Industry Board, Advisory Board for Cardinal Mooney High School, Bradenton Area Economic Development Corporation Executive Committee and Board Member, Economic Development Foundation of Sarasota County Board Member, and Gulf Coast CEO Forum.

Patrick and his wife Jayne reside in Sarasota.  They have three children; Parker and Zack, both graduates of TCU who reside in Texas, and Maddy a graduate of Notre Dame, who resides in Chicago.

COO of Kentuckiana Region | Partner

Trent Hunt

Trent serves as an Executive Partner and COO of our Kentucky Region and an active member of Shepherd’s Mergers and Acquisitions team. In addition, he spends time uncovering new business opportunities for fellow team members on both insurance and financial services platforms. He has nearly 35 years of experience in the insurance industry and is a former chairman of Encova Insurance Groups Advisory Board. Early in his career was the Sales Manager for Indiana Farmers Insurance as well as a Marketing Manager for Encova Insurance Group in their Louisville, Kentucky region. He previously sat on the Executive Board for the Indiana Builders Association as well as the Southern Indiana Builders Association and the Southwestern Indiana Builders Association.  He is a graduate of Indiana University Bloomington with majors in marketing and forensic studies. Trent and his wife Karen reside in Southern Indiana and are proud parents of Andrew and Abby Hunt.

President of Employee Benefits

Matt Kleymeyer

President of Personal Lines and Small Commercial | Partner

Susan Morgan

Before joining Shepherd Insurance in 2014, Susan worked as a Territory Manager at MAPFRE Insurance. She has over 25 years of industry experience on both the company and agency side in areas of customer service, underwriting, sales and territory management.

In her role as President of Personal Lines she ensures that high levels of customer satisfaction are being met by improving ongoing service procedures.  She develops strategies as well as overseeing the day-to-day operating activities of the Personal Lines Division. Additionally, she closely manages the agencies personal carrier relationships to ensure that our customers are continually receiving quality products and services. 

Susan has served on several agent advisory boards for many of our top carrier partners including Safeco, Central Mutual, Hanover, Encova and Secura.

Susan worked as a volunteer with Franciscan Alliance Foundation-St Francis Hospice Foundation from 2009-2016 and is currently a volunteer with the Damar Guild.  She lives in Greenwood, IN with her husband, Wes, and their five kids. She enjoys spending time with family and friends, traveling, playing golf and reading.

Susan’s designations include CPIA. She has received the Bill & Edie Shepherd Leadership Award from Shepherd Insurance 2019. She has also been awarded the Award of Excellence from Safeco Insurance 2019, 2020, 2021. Lastly, she has been recognized as a Blue Streak Underwriter with Central Insurance, active since 2018.

President of Commercial Lines | Partner

Briggs Orsbon

Briggs Orsbon, MBA, UACRM, oversees the operations of the Commercial Lines Department. He is responsible for establishing efficient and consistent processes for all Shepherd offices, which includes both new and renewal business. Briggs is also responsible for coordinating new business marketing strategies across all Shepherd offices. One of his most important responsibilities is fostering carrier relationships and serving on multiple advisory councils for key carrier partners. In 2012, Briggs joined the Shepherd team full-time after serving at Shepherd as an intern. He previously served as Shepherd’s New Business Coordinator and New Business Director. He is currently licensed as a Resident Producer for Property & Casualty and Life & Health. He obtained his MBA from Butler University in December 2015. In 2012, he received his bachelor’s degree in Risk Management Insurance and Financial Planning and Investments, graduating Summa Cum Laude. He was a member of the Ball State football team for four years and served as team captain his senior season. Briggs and his wife, Courtney, have three children: Kennedy, Crew, and Daxton.

CFO | Partner

Steve Strigler

Steve, Chief Financial Officer at Shepherd Insurance, joined the team in June 2024 and holds a pivotal position within the organization. As a Certified Public Accountant, Steve brings a dynamic and results-driven approach to his role. His extensive experience spans multiple industries, encompassing strategic planning, mergers & acquisitions, risk management, accounting, franchising, cash flow management, real estate, and financial reporting. Throughout his career, Steve has consistently demonstrated his ability to implement forward-thinking solutions to drive growth, ensure compliance, and achieve key objectives. Since joining the industry in 2019, Steve’s tenure has been characterized by his unwavering commitment to generating consistent agency growth. He achieves this through a combination of internal improvements, client-centric solutions, and strategic acquisitions. 

Steve earned his Bachelor of Arts in Accounting from Babson College in 1999. His professional journey began with roles in public accounting at PricewaterhouseCoopers. Following this, Steve held various accounting and finance leadership positions in software, real estate, and entertainment. He later transitioned to McDonald’s, a global restaurant industry leader, where he served in various capacities, including his role as the Chief Financial Officer of the Southeast Region.

Steve, originally from Massachusetts, is not only a dedicated professional, but also a devoted family man. He is happily married and takes pride in being a parent to three daughters, including a set of twins. During his time away from the office, he enjoys running, spending quality time with his family, traveling, and passionately supporting his favorite football team, the New England Patriots.

Partner | Mergers & Acquisitions | Benefits Advisor

Austin Akers

Austin Akers, JD/MBA is a Partner who oversees Shepherd’s mergers and acquisitions. He is responsible for the financial analysis, due diligence, and legal support on agency acquisitions. These skills align well with Austin’s role as a benefits consultant.

Austin obtained his JD from Ohio Northern University, his MBA from Butler University, and his Bachelor’s Degree from Eastern Illinois University, graduating Summa Cum Laude. Austin was a member of the Eastern Illinois basketball team and served as team captain during his junior & senior seasons. Austin’s favorite thing to do is spend time with his daughter, Alivia.

Partner

James Anton

Jim joined the agency in 1997 and has earned the Certified Insurance Counselor (CIC) and Certified Risk Manager designations. In addition to marketing and sales, he manages a talented commercial lines team and oversees the loss control and risk management divisions of the agency. Jim participates in various community activities and is a Past-President of the Chesterton – Porter Rotary Club and Duneland Chamber of Commerce. He is the current President of the Northwest Indiana Independent Insurance Agents Association (2015) and is a member of the Indiana Young Agents. Jim and his wife Nicole live in Valparaiso with their daughters Abigail and Sophia.

Partner

Kyle Arnold

Partner

Rob Barnes

Rob is a seasoned risk management and insurance professional with over two decades of experience across the insurance and technology sectors. He currently leads the insurance program for McDonald’s, where he is responsible for managing complex risk transfer strategies, ensuring comprehensive coverage across operations, and leading a team of more than 20 professionals.

Prior to joining McDonald’s, Rob spent over ten years in the technology sector, holding key roles at Hewlett-Packard and an IBM Business Partner. This background has equipped him with a unique ability to integrate analytical rigor and innovative thinking into his approach to insurance and enterprise risk management.

Rob is known for his collaborative leadership style, strategic vision, and ability to drive operational excellence in dynamic environments.

Outside of work, Rob enjoys spending time with his wife Shelley and their two children, Madison and Robbie. When the family isn’t at a dance competition or a sporting event, they’re often out on the water—either fishing or cruising together.

Partner

Lori Brown

Lori is directly responsible for the overall performance of Shepherd’s Columbus and North Vernon locations. She is deeply passionate about investing in the communities surrounding these offices and embedding Shepherd Insurance’s commercial and personal offerings into the lives and businesses of residents. Lori’s book of business is well diversified, with a significant commercial presence in Indianapolis, where she lived for nearly 20 years.

Before joining Shepherd Insurance in October 2013, Lori owned and operated her own data management company in Indianapolis for 14 years. As a former business owner, she understands firsthand the importance of partnering with a high-quality insurance agency when evaluating health benefits, property and casualty coverage, workers’ compensation insurance, and retirement solutions. Prior to starting her own business, Lori held roles as an Accountant, Controller, and General Manager. She earned her bachelor’s degree in Accounting from Indiana University Bloomington in 1992.

Lori is an active member of Zenas Baptist Church, where she currently serves as Sunday School Superintendent. She also volunteers with the Prison Ministry in Jennings County and serves on the Executive Board of the Jennings County Community Foundation. Lori is a Rotarian and Past President of the Columbus Rotary Club. She is currently a member of the Advocates for Children Board of Directors, serving Jennings, Bartholomew, and Decatur Counties, and is an elected member of the local Trustee Board. Additionally, Lori serves as the Treasurer of the Jennings County Swim Club and a member of the Jennings County Food Coalition.

Lori’s husband, Deron, is a school and private psychologist and a high school tennis coach. They have been married since 1990 and have three daughters and one son, as well as a son‑in‑law, Cody, who joined the family in 2021. Lori enjoys supporting her children in their involvement with church, music, athletics, and 4‑H. In 2007, she built a home on her family farm in Jennings County, where she enjoys caring for a variety of animals. Lori loves the outdoors, horseback riding, tennis, running, music, and, most importantly, time with family and friends.

Partner

Jason Bukowski

Jason works in commercial lines and employee benefits for all commercial industries, with a focus on Franchise Truck and Franchise Auto dealerships and Public Entity business including schools, cities, towns and municipalities. He works closely with business owners, as well as supervisors and managers, Jason brings a proactive approach to risk mitigation and claims avoidance. This approach helps him identify any gaps in current coverage, but also aids in premium stability and savings. His past experience in the Employee Health Benefit marketplace allows Jason to strategically help employers navigate the rising costs of healthcare. Jason came to Shepherd Insurance in September of 2011, bringing with him five years of experience with Farmers Insurance Group in Indianapolis, both as a producer and company representative, and one year with SIHO Insurance in Columbus, IN. Jason graduated from the NADA/ATD Dealer Academy program in August 2015, making him the first insurance rep to graduate from this program out of more than 700 alumni. These unique experiences allow him to better understand the operational challenges that lie within franchise truck dealerships and solutions to common dealer issues, while establishing relationships with future truck clients. Jason currently resides in Seymour, IN with his wife Andrea (Ude) and two boys Eli and Henry. Jason grew up in a golfing family and was a four-year lettermen on the Purdue University Men’s Golf Team, where he got to tee it up with some of the best players in the country. He proudly serves Seymour in a variety of ways, including Seymour Main Street Board of Directors and Jackson County Community Foundation. Jason has also served his community as Seymour Chamber of Commerce Board of Directors, Seymour Girls Inc. Board of Directors, past chair of the Schneck Medical Foundation’s Business Relations Committee, and past member of Rotary International.  In 2025, Jason jumped into the coaching ranks, leading the men’s golf team at Seymour Trinity Lutheran High School.  Much of his free time is spent supporting Eli in band and Henry in baseball.

Partner

Jim Burke

Jim is a Senior Sales Executive and Partner at Shepherd Insurance. He started at Shepherd in 1996. Jim specializes in commercial real estate, manufacturing, contracting and hospitality. 

Jim attended Marion high school and graduated in 1988. He then went on to Butler University, where he continued his education and played baseball. 

Jim and his wife Jackie live in Carmel with their dog Colt. He has two daughters, Lauren and Katelyn. Outside of work Jim enjoys playing golf, working out, and spending time with family and friends.

Partner

Ben Coe

Since 2010, Ben Coe has been a trusted advisor to affluent families and successful business owners across the country. As a Partner at Shepherd Insurance, Ben brings a strategic, concierge-level approach to risk management—helping clients protect what they’ve worked hard to build and plan confidently for the future. Known for his discretion, attention to detail, and creative problem-solving, Ben is often referred by clients to their most trusted friends and family.

A graduate of the Insurance and Risk Management program at Indiana State University, Ben has built deep expertise across personal, commercial, and life insurance. He specializes in custom-tailored protection for luxury homes, high-value autos, umbrellas, complex business portfolios, and estate planning strategies involving life insurance. Ben works closely with each client’s financial advisors, attorneys, and family offices to ensure a seamless, comprehensive risk management plan.

In addition to his client work, Ben is passionate about mentoring the next generation of insurance professionals. He dedicates time to coaching and developing young talent within the agency, helping them grow into knowledgeable, client-focused advisors who uphold the same high standards of service and integrity.

Ben lives in Westfield, Indiana with his wife, Elizabeth, their daughter, and their dog. As a family, they enjoy traveling the world, exploring the outdoors, and attending professional football and baseball games in stadiums across the country.

Partner

Robin Cornelius

Partner

JP DeLaney

JP DeLaney is a Partner at Shepherd Insurance, having joined the firm in March 2013 through its predecessor, Logan Lavelle Hunt. With more than two decades of progressive experience in sales and sales management, JP has established himself as a trusted advisor and a leader within the organization. His strategic insight, client-first mentality, and commitment to excellence have contributed significantly to the growth and success of the agency’s commercial and personal lines divisions.

A longtime resident of Louisville, Kentucky, JP is a graduate of Trinity High School and the University of Louisville. Over the course of his career, he has completed numerous industry training programs and certifications, with a specialized focus on both commercial and personal lines insurance. His expertise spans a wide array of risk management solutions, and he is particularly well-regarded for his work developing and managing association-based insurance programs.

JP is known for his ability to build long-standing relationships with clients, carriers, and community partners. He is actively involved in numerous professional committees and regularly collaborates with peers to help shape best practices and improve client outcomes. His leadership extends beyond the insurance industry, as he proudly serves on several nonprofit and civic boards throughout the State of Kentucky. His passion for community involvement is matched by a deep belief in service, mentorship, and collaboration.

Outside of his professional responsibilities, JP is an avid outdoor enthusiast who enjoys boating, golfing, and traveling. However, his greatest joy comes from spending quality time with his family. He and his wife, Beth, reside in Louisville with their two children, Lilly and Austin. Whether on the water, at the golf course, or at home with loved ones, JP values meaningful connections and strives to live with purpose and integrity in both his personal and professional life.

Partner | Sales Executive

Lindsey Epting

As a proud Florida native and seasoned Insurance Advisor, Lindsey bring over 20 years of industry expertise and a deep-rooted commitment to serving her community. Born and raised in Orlando (forever a Disney fan!), her journey has taken her to Florida’s beautiful West Coast, where she has built both her career and family. Lindsey and her husband have shared 18 wonderful years together, raising their son and daughter—her inspiration and, hopefully, the next generation of insurance leaders.

Since joining Shepherd Insurance in 2017, Lindsey has established herself as a trusted advisor known for her integrity, expertise, and dedication to building lasting client relationships. Her passion for insurance was ignited early in her career through grassroots involvement in a local mom’s group, where she became recognized as the “go-to insurance voice” within the community. This reputation, built on clarity, confidence, and genuine care, transformed into a thriving, referral-driven practice. Lindsey believes insurance is about so much more than policies—it’s about understanding lifestyles, anticipating needs, and advocating fiercely for clients as if they were her own family.

Additionally, Lindsey has proudly taken on leadership roles within Shepherd Insurance, mentoring emerging talent and leading Florida sales training events to help shape the next generation of professionals.

Outside of work, you’ll find Lindsey spending quality time with her children and extended family, volunteering with local nonprofits, staying active in her church community, and planning her next adventure to the Great Smoky Mountains—her favorite place to recharge and reconnect.

Partner

Margi Furey

Margi began her insurance career in 1991 in Northern Virginia, where she worked with independent agencies until relocating to Florida with her family in 2007. After the move, she joined Al Purmort Insurance and began working in the Commercial Lines Department. Over time, she advanced from Account Manager—overseeing a diverse book of business—to Commercial Lines Manager in 2012, and later to Director of Special Business Development in 2015.

Throughout her career, Margi developed a strong interest in agency management systems such as Applied and AMS. This sparked a passion for training and mentoring colleagues to ensure they fully understand and effectively utilize these tools as well as other systems used within the agency. 

Margi’s professional passion lies in collaborating with business owners to design customized property and liability insurance programs that protect their assets from loss and litigation. She values educating her clients, so they feel informed and secure in the coverage they choose.

Today, Margi serves in a Training and Development role at Shepherd Insurance as the Training and Development Manager, where she focuses on onboarding and educating employees on Commercial Lines processes and systems. She is committed to cultivating a knowledgeable and confident team that delivers exceptional service and solutions.

Outside of work, Margi is deeply connected to her Sarasota and Manatee communities. She volunteers with several organizations, and two that are especially close to her heart are Girls Inc. of Sarasota and Living Lord Lutheran Church. When she’s not helping others or working with her team, you’ll likely find her enjoying Florida’s beautiful outdoors or spending quality time with her family and friends.

Partner | Employee Benefits

Steve Gregory

Steve Gregory serves as the President of Employee Benefits that leads Shepherd’s Employee Benefits division. He is called upon for his expertise in financial evaluation, benefit design and implementation of risk management strategies for employer-sponsored health and wellness plans. Additionally, he performs insurance contract analysis, vendor assessment, claims analysis and overall plan reviews.

With over 32 years of experience in the insurance industry, Steve engages as a public speaker on issues relating to strategic planning, alternate funding strategies and the employee benefits landscape. In addition to his time at Shepherd, Steve serves on the Board of Prevail, Inc. and the Forte Sports Medicine Research & Education Foundation.

Steve is a graduate of Indiana University and is married with two daughters. During his free time, he loves being with his family, skiing, and competing in triathlons

Partner

Robbi Gwaltney

As Partner and Vice President of Personal Lines, Robbi Gwaltney helps lead the strategic growth and operational excellence of Shepherd Insurance’s Personal Lines division. She has played a key role in developing service models, workflows, and departments that support agency growth while enhancing the client experience. Robbi is passionate about leveraging technology, data management, and emerging AI tools to improve efficiency, strengthen service delivery, and help teams succeed. She also works closely with clients and carrier partners to build long-term relationships, resolve complex insurance challenges, and provide trusted guidance during times of change or loss.

Robbi joined Shepherd Insurance in November 2011 and brings more than 28 years of insurance industry experience, with a strong focus on personal lines and private client services. Throughout her career, she has served in client-facing, operational, and leadership roles, helping organizations drive growth, improve processes, and deliver exceptional customer service. Her extensive industry knowledge and expertise in agency operations make her a valuable resource for both clients and colleagues.

Robbi lives in Indianapolis with her husband, John, and is the proud mother of four grown daughters and grandmother of six grandchildren. Outside the office, she enjoys reading, exploring new interests, and tackling what her husband affectionately calls her “Project of the Week.” Whether she’s learning a new skill or enjoying a good cup of coffee, Robbi’s curiosity and enthusiasm keep her constantly engaged and inspired.

Partner | Regional New Business Manager

Kari Haston

As Partner and Regional New Business Manager, Kari Haston leads mid-market new business placement efforts throughout Shepherd Insurance’s Kentuckiana region. With more than 20 years at Shepherd, she works closely with producers and carrier partners to develop insurance solutions for prospective clients and support agency growth. For the past 10 years, her primary focus has been on new business strategy and placement.

Kari began her career with Shepherd Insurance as an intern in August 2005 while completing her Business Management degree at the University of Louisville. Since then, she has held a variety of roles across the organization, giving her a broad understanding of the agency and the insurance marketplace. She holds both the Certified Insurance Counselor (CIC) and IA-MBA designations.

Outside of work, Kari enjoys spending time with her family and cheering on her two children, Maddie and Marcus, at their sporting events.

Partner

Daniel Herrenbruck

As a Partner with Shepherd Insurance and leader of one of the agency’s Naples, Florida, offices, Daniel Herrenbruck works with individuals and families to help protect their assets through personal insurance solutions. Drawing on 20 years of industry experience, he focuses on understanding client risks, providing practical guidance, and building long-term relationships.

Daniel joined Shepherd Insurance in 2025 after nearly two decades in the insurance industry. He began his career in the captive agency environment before transitioning to the independent agency model in 2022. Daniel holds a Bachelor of Science in Finance from Indiana State University.

Daniel lives in Naples with his wife of more than 20 years, Erin, and their three children, Hope, Evan, and Eli. Outside of work, he enjoys sports, spending time outdoors, and coaching youth athletics. He is actively involved with First Naples Church and serves as a varsity girls flag football coach.

Partner | Employee Benefits Consultant

Andrew Hunt

Andrew Hunt is an Employee Benefits Advisor at Shepherd Insurance and has been with the organization since graduating from Indiana University in 2017. Over the past eight years, Andrew has focused on helping organizations identify financial opportunities and develop health insurance strategies that align with their unique goals, workforce needs, and long-term vision.

Specializing in employee benefits consulting, Andrew is passionate about building lasting relationships with clients and guiding employers through the ever-changing healthcare landscape with thoughtful, customized solutions. He takes pride in delivering strategies that balance cost management with meaningful employee benefits and support.

Outside of his client work, Andrew previously served as a board member for Cherish Child Advocacy and enjoys mentoring younger Shepherd associates who are looking to find their path within the insurance industry, much like he did early in his own career.

Andrew and his wife, Melissa, enjoy attending Indiana Hoosiers sporting events, traveling, and exploring new restaurants and food experiences together.

Partner

Jeff Johnson

With specialized focus in a handful of industries including motorsports, contractors, garage operations, manufacturing and real estate, Jeff Johnson works with Shepherd clients to determine how to best protect their people, their businesses and their teams. He takes great pride in remaining accessible to clients whenever they need him, 7 days a week, and his focus on niche industries helps him to understand his clients’ needs more thoroughly.

A third-generation insurance agent, Jeff attended Indiana State University, where he studied Insurance & Risk Management. He began his insurance career in 2000 and joined Shepherd Insurance in 2012.

Jeff has continued to advance his career while at Shepherd.  In 2019 Jeff won Shepherd’s Regional Sales Excellence Award, followed by 2020 where he was named Partner at Shepherd. He and his father, “Team Johnson”, were awarded the 2020 National Sales Excellence Award.

Jeff was named the Indiana Big I Independent Agent of the year for 2021.  This is considered one of the highest honors available in the independent agent community.

Jeff and his wife Rachel have three children and a Silver Labrador and live in Fishers. His love for racing started early – attending his first sprint car race when he was just 8 weeks old. Along with spending time with his family, Jeff also enjoys golf, boating, and coaching little league.

Partner

Jacob Julius

Prior to starting in the insurance industry, he pursued a career in professional baseball. Jacob played 5 seasons in the Baltimore Orioles minor league system, topping out at AAA after being drafted from the University of Arkansas. 

Jacob has used that same work ethic to partner with companies of all sizes to help solve their business insurance challenges. He specializes in creating risk management strategies including workers compensation and builders’ risk. He spends a lot of his time in the real estate and construction industries. He is passionate about partnering with clients to help them protect what is most important to them. 

Jacob and his wife Meghan have three children – Ethan, Dolle and Bowman. They are lifelong residents of Southern Indiana and enjoy spending time with their family and being active in the local community. Jacob has served on numerous boards and is currently a board member of the Indiana Builders Association and the Harrison County YMCA. He also coached baseball at Providence High School for parts of 8 years, where the team won state titles in 2016 and 2021.

Partner

Nita Knies

As Vice President of Commercial Services, Nita K. Knies (CIC, API, CISR, AINS) is responsible for the entire commercial lines service division of Shepherd Insurance. Nita manages the customer service team and works to develop and maintain excellent customer service standards. Nita serves as a mentor to our staff and consistently provides assistance and the tools necessary to help our employees set and achieve career goals which in turn results in career growth within our company. She works constantly with our entire commercial lines team to access our processes and procedures to make sure we are always a step ahead in the insurance service industry.  

Nita brings her 30 plus years of insurance expertise to the Shepherd team, joining in 2014 via the Consolidated Insurance Services merger. Specializing in management, personal, commercial and life & health insurance, she is able to be utilized in a variety of capacities by the company. Nita serves as member on the Professional Insurance Associations Certified Insurance Service Representative (CISR) committee. She has been a Certified Insurance Counselor (CIC) for 25 years. In 2019 Nita was awarded Shepherd’s Manager of the Year Award and in 2020 was named a Partner in the organization. Also in 2020, Nita received Shepherd’s highest honor the Bill & Edie Shepherd Leadership Award.  

For pleasure Nita likes to travel and take in concerts. She inherited a love for dancing and live music from her parents and will take every opportunity for a dance! Nita makes her home with husband Glenn. The couple have two children Jon, who is also making a career with Shepherd Insurance and Lindsey currently studying at IUPUI.

Partner | Director of Finance

Lissy Koors

As Partner and Director of Finance, Lissy Koors oversees the financial operations of Shepherd Insurance. With more than 20 years of insurance industry experience in accounting and finance, she manages financial reporting, planning, budgeting, and analysis while supporting the agency’s long-term growth and operational goals.

Prior to joining Shepherd, Lissy spent 10 years with a publicly traded national insurance broker, where she held positions in internal audit and regional financial management. Her experience includes acquisition due diligence and integration, system conversions, annual budgeting, and strategic planning. Lissy earned her degree from Purdue University’s Krannert School of Management.

Lissy lives in Carmel with her husband and three children. Outside of work, she enjoys exercising, reading, traveling, and spending time watching her kids participate in sports.

Partner

Stan Logan

Stan graduated from the University of Kentucky and The College of Insurance in New York. Past Certified Insurance Counselor. Currently President of PIA services. The for-profit arm of PIA National. Past President and Trustee on Local Fire Department Board. Past PIA agent of the Year. Stan has a passion for boating and spending time with friends and family.

Partner

Dena Shepherd London

As she approaches her 25th year with Shepherd Insurance, Dena brings a wealth of experience in Commercial, Personal, and Life Insurance. She is passionate about building lifelong client relationships and helping individuals, families, and business owners protect what matters most through thoughtful, customized insurance solutions.

Known for her exceptional service and attention to detail, Dena serves as a trusted advisor and advocate for her clients, working closely with insurance carriers to deliver thoughtful guidance and seamless support. She has significant experience serving high-net-worth clients and specializes in comparing coverage across multiple top-rated insurance companies to provide the strongest protection and greatest value.

A proud graduate of Carmel High School and Purdue University, Dena lives in Carmel with her husband, John London, Vice President at Planes Companies. Together, they have three sons – Nolan, who proudly serves in the United States Army, and Trey and Jonah, who have the rare and special opportunity to play high school basketball together.

Deeply rooted in her faith and community, Dena strives to live a life of purpose centered on service, health, and personal growth. She is passionate about empowering and mentoring women, encouraging them to build confidence, embrace accountability, and create meaningful connections.

Partner

John Long

John Long (AAI,TRS) joined Shepherd Insurance in 2014 as risk management consultant in our Property & Casualty department and quickly grew to become a Partner in the firm. John functions as a consultant in our Transportation practice group and manages accounts in the Real Estate and Environmental industries as well. His experience has allowed him to gain extensive knowledge in the strategy, design and administration of large deductible and self-insured retention plans along with captive insurance alternatives.

John and his team work to better serve clients by first understanding the company’s top initiatives, then designing a tailored risk management solution in alignment with those initiatives.

Partner

Ross MacLennan

Ross is a seasoned insurance professional with a wealth of knowledge and experience in the industry. He graduated from Indiana University Bloomington School of Business in 1985.  Following an internship with Commercial Union, he embarked on a career at MacLennan & Bain Insurance in January 1986.  With a commitment to professional development, Ross has earned the prestigious Chartered Property Casualty Underwriter (CPCU) designation. This designation signifies exceptional knowledge and proficiency in the property and casualty industry.  Ross specializes in commercial and professional liability with a unique niche in healthcare malpractice insurance.  

Ross made the decision to join forces with Shepherd Insurance in 2024 and looks forward to continuing to serve his customers with the added strength Shepherd brings.

Partner

Chris Maynard

Chris Maynard (MBA, AAI) started with Shepherd in March 2014. Prior to starting in the insurance business, Chris worked in sales for various pharmaceutical and medical device companies within the healthcare industry. Building on that experience, he has used his industry knowledge to help employers limit waste and provide better benefit solutions for their employees.  He is passionate about providing benefit plans tailored specifically to the employers’ needs and is well-versed in the various financial levers that can be utilized within a plan to control costs and risk.  Chris also manages the southwest Indiana region for Shepherd.

Born and raised in Evansville, Indiana, he is a graduate of Mater Dei High School. Chris attended Lewis University and played collegiate baseball for the Flyers.  He received his BA and MBA from Lewis.

Chris and his wife, Alissa, have a daughter, Reese, and three sons, Chase, Jackson, and Brooks. They are members of Good Shepherd Catholic Church and School. In his free time, Chris enjoys watching his children participate in all of their activities and traveling with his family. 

Partner

Joshua McCarthy

Joshua McCarthy began his insurance career in 2000 as an intern for a Life Insurance & Annuity broker. That same year, he earned his Property & Casualty license and transitioned into a sales and service role as a captive agent. His early success was marked by multiple awards, including the Sales Excellence Award in 2003 for personal lines and membership in the Million Dollar Annuity Club in 2004.

After relocating to Nevada, Joshua shifted his focus to management and leadership, earning the “30 Under 30” award. He advanced into a Sales Management role with a bank-affiliated insurance agency, where he discovered a passion for the Independent Agency channel. Promoted to lead the entire state, Joshua guided his team to national recognition, earning Cornerstone status from Chubb for multiple consecutive years, being named #1 Agency nationwide by MetLife, and receiving honors from West Bend Mutual, Fireman’s Fund, and Auto-Owners, while also qualifying annually for the Travelers Sales Excellence Trip.

Joshua was later promoted to Vice President, overseeing personal lines sales across Wisconsin and Arizona.

Following a move to Florida, he pursued entrepreneurship by earning his contractor’s license and launching a Pool Heating and Outdoor Kitchen business. Under his leadership, the company achieved ELITE status with HomeAdvisor and won the Social Media Marketing Award from the Florida Swimming Pool Association. 

During the pandemic, Joshua sold his business and returned to the insurance industry, joining Shepherd Insurance as Personal Lines Manager. He was promoted to Regional Manager, and in 2022, he was honored as Manager of the Year. In 2024, he became a Partner, and in 2025, he was promoted to a national leadership role as Director of Personal Lines, where he now focuses on Shepherd’s entire footprint across the country.

Joshua is also deeply committed to community service. He has served as Secretary of a local Kiwanis Club, held the title of “Esteemed Loyal Knight” at the Elks Lodge, contributed to the Membership Committee of the Las Vegas Chamber of Commerce, and was recognized as New Member of the Year with BUSE Las Vegas. He also served as an Ambassador for the Nevada Pest Control Association.

Joshua earned his IA-MBA, a specialized program designed for independent agency Leadership and completed a Certificate in “Organizational Leadership” from Harvard Business School Online, further strengthening his strategic and leadership capabilities.

Joshua and his wife have been together for 20 years and are proud parents to an amazing daughter. They reside in Florida, where Joshua enjoys the beach and pool Life.

Partner

Ryan McCarty

Ryan McCarty, CIC is a partner and manages the Northern Kentucky location. He oversees the daily operations of sales and service. Ryan is a mentor to the sales team and provides the leadership necessary for his team to effectively operate at a higher standard.

Ryan earned his BA in Business Management from Northern Kentucky University.  He has worked in the insurance industry for over 20 years. He has served on several insurance boards, and currently serves as a board member with the PIA of Kentucky. Ryan is also on the Board of Directors for the Matthew Mangine Jr. Foundation. This foundation provides education and training to parents, coaches and athletes on implementing proper emergency action plans in youth sports. Additionally, it provides financial support for necessary life-saving equipment for schools in need.

Ryan and his wife, Brandy, have two children, Carson and Sophia.

Partner

Fred McClaine

Fred McClaine has assisted business owners as their strategic insurance consultant for over 35 years. He is a holistic consultant, analyzing the business not just for insurance, but what is needed in avoiding risk in the ever-evolving world today. Fred helps explore Insurance coverages and premiums that best suits a business plan. Serving all lines of business, Fred specializes in business risk management including Directors & Officers Liability, Professional or Errors & Omissions Liability, Medical Malpractice, Cyber Liability & Data Breach, Employee Benefits, and business financial planning for owners and key executive employees.

He began his career with AAA as a leader of their largest office in Indianapolis. After ten successful years, Fred started a private Property & Casualty insurance brokerage as a marketing partner with of Lincoln National Life. That company merged into Agency Associates, Inc. (AAI) and he became their president in 1996. The agency had 800% of dynamic organic growth during Fred’s tenure as president. AAI then merged with Brown & Brown Insurance, the sixth largest agency in the nation. McClaine led their Indiana operations, and it became the largest insurance agency in the state during his six years. McClaine joined the Shepherd team in May of 2014 as Senior Consultant and became a Partner in 2016.

At Shepherd Insurance, McClaine has driven growth of the Medical Professional Liability division to become one of the largest and most respected in the Midwest. He works with his team and clients all over the country advising on business insurance needs.

McClaine is a graduate of The Scott School of Business at Indiana State University with a BS in Marketing. In the insurance industry, he served as president of the Greater Indianapolis IIAI, was president of the Young Agent’s Council, and was also the IIAI Young Agent of the Year. Fred is a member of the Indiana Medical Group Management Association (IMGMA) and the Indiana State Medical Association (ISMA).

Fred has served on numerous boards including the Marian University Committee for Scholarship & Educational Advancement, the Sands Resort Strata Board in Turks & Caicos Islands, co-founder, and Chairman of the Board of “Exodus90” a Catholic Men’s educational group influencing men all over the world to live their life free of the trappings of society.

Partner

Brad McNulty

Brad McNulty works closely with many of the largest franchise truck dealers in the country helping them analyze and implement the best garage liability and workers comp packages available in the marketplace.

Brad has been with Shepherd Insurance for over 25 years. Prior to joining the Shepherd team, he was the general sales manager at Palmer Dodge on the north side of Indianapolis. Before that, he coached college basketball at Ball State University and the University of Wisconsin from 1976 to 1989.

A true lifelong Hoosier, Brad grew up in Kokomo and attended Purdue University, on a basketball scholarship, where he earned his degree. Brad is passionate and committed to helping Shepherd Insurance continue to grow and be successful in the future. When not working Brad enjoys traveling with his wife Lissa around the US and abroad to attend big Thoroughbred races, along with the breeding and racing of Thoroughbreds. He lives in Westfield with his wife of 42 years, Lissa. They have one son, Matthew, who lives in Zionsville.

Partner

David Moore

David graduated from Ball State University in 1984.  After graduation, he joined his parents in the insurance industry at John Moore Agency in Seymour, IN. While living in Seymour, he earned his CIC designation in 1987 and served on the advisory council of Citizens Insurance Company (now part of Hanover). He also served locally as Board President of Girls, Inc., as a member of the Membership Services Committee for the Seymour Chamber of Commerce, and as an elder at his church.  He also was heavily involved with coaching his kids in basketball, baseball and softball.

In 1998, David purchased the agency from his parents and continued to grow the book until merging with Shepherd Insurance in 2007, becoming the second agency-partner to join the company.

In 2016, David moved to Scottsdale, AZ, and helped grow the Arizona footprint which now includes offices in Payson, Prescott, and Tucson, AZ. He has kept in touch with his Indiana clients during the move and continues to grow his book of commercial, benefits, life, and high net worth personal lines business. He serves as a resource to several attorneys, financial planners, and advisors in the area and assists people in different parts of the country by solving their professional liability needs. He also acts as a liaison to our partner agencies in Arizona, serving as a conduit to the staffs and helping them learn the Shepherd way of doing business.

David’s wife, Shannon, is also a Shepherd employee now, helping seniors navigate the Medicare marketplace. They have three children – Ashley, Nick, and Amanda – and two grandchildren.  In his spare time, he enjoys running, hiking, playing golf, and traveling the west coast.

Partner

Susan Morrison

At the age of 19, Susan began her career in the insurance industry as a receptionist at House-Chilson & Associates agency in Prescott, AZ. The owners must have thought she had promise because she was quickly promoted to a personal lines producer, then became a commercial lines producer and ultimately acquired 50% of the agency upon the retirement of one of the agencies original partners. In 2019, she and her business partner sold the agency to Shepherd Insurance where she remains as a senior sales executive and oversees the day-to-day operation and management of the Prescott office.

In her spare time, when she is not trying to keep up with her young daughter Journey, she enjoys volunteering within the community and her church. She has served as Chaplain and Vice-President for the Fraternal Order of Eagles Women’s Auxiliary.

In addition to her professional endeavors, her proudest accomplishment is having the opportunity to raise her daughter and be a positive influence in her life.  She is looking forward to the future with Shepherd and seeing what can be achieved together as an organization.

Partner

Matt Nance

As a Partner with Shepherd Insurance, Matt Nance leads one of the agency’s Naples offices, as well as its Estero, Florida, location. He remains actively involved in client relationships and team development while overseeing operations and supporting the continued growth of Shepherd’s Southwest Florida market.

Matt is originally from Mount Vernon, Indiana, and began his insurance career in 2006. A graduate of Anderson University with roots in the Midwest, he has built and led a successful independent insurance agency serving clients throughout Southwest Florida. Under his leadership, the agency earned recognition as a Big “I” Best Practices Agency in 2025, reflecting its commitment to operational excellence and personalized service before joining Shepherd in April 2026.

Matt and his wife, Casey, have been married since 2009 and have two daughters. Outside of work, he enjoys traveling with his family, building connections within the community, and spending time outdoors. He has served in leadership roles within his homeowners association and local church and shares his home with Millie, a playful Portipoo.

Partner | Regional Commercial Lines Manager

David O’Bryan

David O’Bryan serves as an Associate Partner and Regional Commercial Lines Manager for Shepherd Insurance’s Kentuckiana Region, where he leads a high-performing service team focused on collaboration, accountability, and delivering a best-in-class client experience. In his role, David is responsible for driving retention, strengthening client relationships, and advancing service strategies that support long-term growth across the region.

David works closely with leadership and frontline team members to continuously refine workflows, elevate service standards, and empower his team to make confident, client-focused decisions. David is passionate about building strong teams and has played a key role in developing talent, improving operational consistency, and aligning day-to-day execution with Shepherd’s broader strategic vision.

David joined Shepherd in July 2020 and brings more than 20 years of insurance industry experience, with a background spanning both the independent agency and carrier sides of the business. A Certified Insurance Counselor (CIC), he has developed deep expertise across a wide range of commercial lines disciplines and remains a strong advocate for the independent agency model.

A lifelong resident of Louisville, KY, David earned a double major in English and Communications from Bellarmine University. Outside of work, he is actively involved in his community and church, where he and his wife, Alex, sing in the choir and David serves on the Finance Committee. Together, they are proud parents of their 10-year-old daughter, Adley.

Partner

Skip Oliver

Skip began his started my insurance career in 2007 with Farmers Insurance. In 2011, he went to work for Dean Webster Insurance. Dean Webster Insurance was acquired by Shepherd in 2016. With the help of his friend and mentor, Doug Annakin, his career and focus on Commercial Lines took off.  In his second full year with the company, Quinn and Shepherd took a chance on me and opened an office in Carmi, IL. The first full year, he was blessed to win the Agent of the Year. He has since added a Regional sales award. His focus and niche is now in the oil and gas industry. He has developed strong relationships with the three oil and gas associations in the area. Developing this niche has given Shepherd the opportunity to become a trusted agency in the industry.

A lifelong west-sider, Skip graduated from Reitz High School then, the University of Southern Indiana. Skip has two children, Devin and Mya and is in a long-term relationship with Lindsay Botsch. Lindsay is the current Evansville Market President at German American Bank. When not working, Skip enjoy fitness and has become an avid runner.  He has competed in the country’s largest marathons, Chicago, New York and Boston, several times

Partner

Miles Parker

Miles was born and raised in Bedford, Indiana.  He attended Indiana University in Bloomington and graduated from the School of Business in 1995.  Miles began his career at Toyota Motor Sales in Torrance, California and returned to Bedford in 1996 to join his family insurance business.  He handles all lines of insurance, including Commercial Property & Casualty, Employee Benefits and Personal Insurance, specializing in complex placements with a consultative focus. Miles enjoys spending time with his wife, Blaine and their two daughters, Vivienne and Sophie.    

Partner

Clark Pence

Clark Pence is a Partner and the Director of Towing for Shepherd Insurance. As Director of the towing program, he is responsible for retention, overall growth of the program, and maintaining relationships with carriers. While doing so, he continues to develop new relationships with carrier partners, and quoting new business while managing his own book of business.   

Clark joined Shepherd Insurance in 2016 after graduating from Northern Kentucky University and was a member of the baseball team. Clark resides in Carmel with his wife Cara, their son, Parker, and their two dogs, Woodford and Sheldon. In his spare time he enjoys golfing, cheering on the Colts & Pacers and spending time with his friends and family.

Partner

Shannon Russell

With 30 years of employee benefit consulting experience, Shannon uses her knowledge of employee benefits and industry trends to design custom solutions to meet client objectives and budgetary constraints.  She excels in structuring plans, conducting program analysis and leveraging resources to advise cutting edge strategies for my clients.  

She is a graduate of Purdue University with a major in Mathematics.  She began her career in employee benefits working as a large group underwriter for Indiana’s largest insurer and has been consulting directly with large, multi-state clients since 1998.

She was born and raised in a tiny town in southern Illinois and moved to Indianapolis in 1992, never leaving. She now lives in Fishers with her ten-year old son, Fletcher, and her thirteen-year old dog, Franklin.  In her spare time you’ll find her reading or spending time with family.

Partner

Derek Rogers

Derek Rogers, CRM is a Partner and Sales Executive for Shepherd Insurance.  As a second-generation insurance professional, Derek earned his degrees in Risk Management & Insurance and Business Administration from Ball State University in 2011.  Upon graduation, Derek joined Shepherd Insurance in 2012.  He obtained his Certified Risk Manager designation in 2016.  Derek specializes in commercial lines property & casualty insurance.  

Born and raised in Greenfield, IN, Derek is an active member of the community.  Derek is a third generation Rotarian and Past President of the Rotary Club of Greenfield.  He has also served as a Past President and board member of the Boys and Girls Clubs of Hancock County since 2015.  

Derek and his wife, Amanda, have two children, Sophia and Sydney.  Derek and his family attend Brandywine Community Church.  In his free time, Derek enjoys basketball, golf, coaching his children’s sports teams, along with cheering for the Colts, Pacers, Reds, and IU. 

Partner

Paul Schafer

Paul is responsible for managing and growing a commercial and personal book of business in Indianapolis that is comprised of many former Consolidated Insurance Services clientele. Prior to joining Shepherd, Paul worked for Consolidated Insurance Services, Inc. and served as a Producer / Vice President / Principal / Partner. He began his career at C.N.A Insurance Companies: Senior Sales Representative and also worked at Indiana Insurance Company as aTerritory Manager.

Paul currently serves on the Board of Directors for the Indianapolis Police Department Motorcycle Drill Team, Citizens Speedway Committee / Indianapolis Motor Speedway, Hoosier Suds Foundation, American Business Club and the Big I Indianapolis. He has previously served on the board of the Indiana Motorsports Association., the Sports Car Club of America and the Lambda Corporation.

His hobbies include: Vintage Car Collecting and Racing, Cooking / BBQ, White River Yacht Club., BMW Car Club of America., Mercedes Benz Car Club of America, Porsche Club of America, Sports Car Club of America and the Indianapolis Triumph Club. Paul is married to Jill Fewell. Director, ‘Welcome Home Vietnam Veterans’ Non-Profit and affiliated with the Indiana Department of Veteran Affairs. He has two Stepsons: Isaac Fewell 24 and Jeremy Fewell 28. He is a graduate of Indiana University. With a BA in Telecommunications and Marketing. He was a member of the Sigma Chi Fraternity.

Partner

Paige Sexton

With over two decades of experience at Shepherd Insurance, Paige Sexton manages more than $18 million in premiums nationwide, with a 95% focus on truck dealerships. She collaborates closely with producers and executive leadership to build and maintain strong client relationships, specializing in tailoring coverage strategies to meet the evolving needs of each business. Her responsibilities also include overseeing renewals, proposals, audits, and claims, as well as leading monthly educational sessions within the truck dealership division.

Paige’s excellence in customer service has been recognized with several prestigious awards, including the Shepherd Insurance Customer Service Agent of the Year (2005), the Distinguished Customer Service Representative Award from the Independent Insurance Agents of Indiana (2016), and the Shepherd National Marsha Baker Customer Service Agent of the Year (2024).

Before joining Shepherd in 2000, Paige built a strong foundation in the banking industry, bringing valuable financial insight to her current role. She has held her CIC, CRM, and CISR designations since 2006, reflecting her commitment to professional development and industry expertise.

A graduate of the University of Evansville, Paige has been married to her husband Greg for 29 years. Together, they enjoy spending time with their children, Savannah and Wyatt. As a proud Army family, they honor Greg’s 20 years of service, including two deployments to the Middle East and his recognition as a Purple Heart recipient. Their family also includes two beloved dogs—Lincoln, Greg’s Yellow Lab service dog, and Roxie, a spirited Yorkie Terrier.

Paige is an active member of Noblesville First United Methodist Church, where she participates in mission trips to Give Kids the World and Guatemala, serves as a regular usher, and has been a Stephen Minister. She and Greg are also involved in the Pets Healing Vets program through the Humane Society for Hamilton County, which pairs shelter animals with veterans coping with PTSD or TBI. Additionally, Paige is a dedicated member of Phi Beta Psi, a national civic sorority that raises funds for cancer research.

In her free time, Paige enjoys reading, watching movies, crocheting, crafting, baking, and cake decorating.

Partner

Nathan Shanks

Nathan Shanks is a Partner at Shepherd Insurance, where he has built his practice around helping business owners and real estate operators understand, manage, and transfer risk with confidence.

With 10 years in the industry, Nathan brings a perspective that most retail agents don’t have. He started his career on the wholesale side, giving him firsthand exposure to how complex accounts are underwritten, priced, and placed across specialty markets. That background shapes how he approaches every client relationship today. He joined Shepherd in 2018 and has focused his practice on commercial real estate, development, construction, manufacturing, and hospitality, working with clients who need more than a policy renewal and a certificate holder.

Nathan is passionate about education. Whether it is walking a client through a coverage gap they didn’t know existed or sharing insights online with business owners and investors navigating risk for the first time, he believes that an informed client makes better decisions. That commitment to transparency and plain-language advice is at the core of how he works.

Outside the office, Nathan is active in the Louisville community and invests time in building relationships that go beyond the transaction. When he is not working, you will find him on the golf course, traveling with his family, or working through a good book. He lives in Louisville with his wife Sarah and their two kids, Collins and Sam.

Partner | Mergers & Acquisitions

Steve Shepherd

Steve began his insurance career in 1983 after graduating for the University of Indianapolis. He sold his agency (S.R. Shepherd Insurance Agency) in the mid-1990s to merge with his brother, Dave … and the rest, as they say … is history.

After prospecting, selling, and servicing all lines of insurance for over 40 years, Steve now dedicates his time to the merger and acquisition arena. He is responsible for prospecting successful, independent agencies that are seeking the strong connection and the defined culture that fits the Shepherd model.

Steve was born and raised in Carmel, IN. A member of the 1977 Boys State Championship Basketball Team and a 1979 graduate of Carmel High School, he attended Indiana Central University (now University of Indianapolis) on a basketball scholarship and majored in education. He now has 3 children and 5 grandchildren. In his spare time, he enjoys golf, tennis, travel, music venues, spectator sports and a good game of euchre with family and friends.

Partner

Jeremy Sims

Jeremy Sims is a Partner and Senior Sales Executive at Shepherd and works with New Franchise Truck Dealerships and Middle Market businesses to help them define their risk management goals and put the proper protection in place. He is responsible for prospecting, renewing and implementing insurance programs for Shepherd’s National Franchised Truck Dealer Program. Jeremy also helps coordinate Captive analysis and placement, sales training and coverage analysis with Shepherd’s team members and carrier partners.

Jeremy joined the Shepherd team as a sales agent in 2008, after previously working at The Bridgewater Club. He attended the University of South Florida, where he was a member of the men’s golf team.

Partner

Matt Smith

Matt Smith (CRM) is the Director of Dealership Programs for Shepherd Insurance. As Director he is responsible for retention and overall growth of the program, maintaining relationships with carriers, developing new relationships with carrier partners, quoting new business, and managing some larger accounts within the department.   

Matt specializes in creating insurance solutions for the needs of his diverse clientele by focusing on unique exposures for Franchise Truck Dealerships, in the garage liability and lease/rental space.  He works with insureds to review exposures, negotiate renewal terms, and helps insureds review their overall risk appetite.  

Matt obtained his degree from Ball State University, majoring in Risk Management and Insurance.  He joined the Shepherd team in 2008 working as an intern for the commercial department.  After graduating, Matt accepted a position as an account manager in the Franchise Truck Dealer Department, and has held a CRM designation since 2011.  Matt, his wife Jaclyn, and their daughter Averie reside in Westfield, IN.

Partner

Angela Smith

Angela oversees the commercial lines team for Shepherd Insurance in the Florida region. She is responsible for managing key accounts, driving new business sales, and ensuring exceptional customer satisfaction. Since joining the company in 2013, she has leveraged her 15 years of insurance expertise and over 30 years of professional experience in the automotive industry and business start-ups to enhance service delivery and operational excellence.

Angela holds a degree from the University of Houston and has completed advanced studies at the PIPI Finance School in Oregon. She also earned a degree in Culinary Arts from Le Cordon Bleu in Scottsdale, Arizona.

A lifelong horse enthusiast and avid dressage rider, Angela enjoys spending time at her ranch with her three daughters and two grandchildren. Previously, she served on the board of the Girl Scouts of the Gulf Coast for three years, demonstrating her longstanding commitment to youth and community development.

Angela currently serves as the Secretary/Treasurer of SMART, where she brings her passion for therapeutic horsemanship and her extensive leadership experience to the organization. A dedicated volunteer, Angela is committed to helping SMART fulfill its mission of providing therapeutic services through equine-assisted activities.

Partner

Stephen Strong

Steve Strong is a partner and became a Licensed Insurance Agent 1994. He earned his Certified Insurance Counselor (CIC) 2010 and obtained his Property and Casualty Consultant License in 2017. He has been the endorsed insurance agent for the KY Association of Master Contractors (KAMC) since 2009. He has also served on the Executive Board of Directors for the KY Association of Master Contractors for the last 8 years.

His interests include his faith in God, his wife Angela, and their four-legged children. Stephen also enjoys sports particularly, golf and football. He is grateful and blessed to serve the needs of his clients. His mission as a Partner of Shepherd is to provide a greater and measurable value to clients he serves. He does this by always being accessible to his clients, providing qualified information to help them make the correct decisions and being ready to hold their hands through the claims process. 

Partner

Kyle Turner

Kyle is a 2^nd generation agent specializing in property & casualty insurance. He started a scratch agency in his hometown of Centerville, Indiana, Turner Insurance, in 2004 and partnered his agency with Shepherd in 2020. 

Kyle graduated from Ball State University with a degree in Marketing and began his career in insurance sales in 1994.  Kyle obtained his Certified Insurance Counselor accreditation in 2006 and has served on the board and as President of the Professional Insurance Agents (PIA) of Indiana. Kyle currently serves his community as board President of the Centerville Abington Dollars for Scholars, and steering committee board member for Forward Wayne County. He has previously served as secretary for the Economic Development Corporation of Wayne County (EDC), and was a board member and past president of Main Street Centerville, Inc.

Kyle & his high school sweetheart wife Mynde live just outside of Centerville in a big Red Barn and enjoy traveling, live music, sporting events & frequent weekend trips to Cincinnati.

Partner | Director of Sales & Development

Andy Warren

Andy is Partner and Senior Sales Executive at Shepherd Insurance.  He has developed risk management strategies serving all lines of business including commercial property & casualty, employee benefits, and personal insurance programs.  Andy also engages his clients on the benefits of life insurance, buy-sell agreements, key-man life insurance, and financial services.  As a sales executive at Shepherd Insurance since 2006, licensed in both property & casualty and life & health, Andy has over a decade of success in organic sales and retention.  His overreaching goal is to bring the greatest value to his clients, and to help his clients reach their long-term goals and objectives.  In addition to his time at Shepherd Insurance, Andy serves on the not-for-profit boards of the Carmel Dad’s Club and Cherish.  Andy is a graduate and former basketball player at Carmel High School and Anderson University.  He was later a successful assistant basketball coach at Guerin Catholic High School in Noblesville where the Golden Eagles won two state championships.  Andy now lives in Carmel with his wife Jessica and their three children Mason, Roman and Gemma.

Insurance Advisor | Associate Partner

Melissa Collins

Melissa Collins serves as an Associate Partner, Trusted Insurance Advisor, and Office Manager for Shepherd Insurance’s Tucson, Arizona office. Bringing more than 21 years of industry experience, Melissa joined Shepherd in 2019 and assumed a leadership role focused on the growth and development of the Tucson office. During her tenure, she has helped expand service offerings through the commercial lines business while continuing to support clients throughout the region.

Known for her compassionate leadership style, Melissa is dedicated to building meaningful relationships with clients and cultivating a supportive, family-oriented culture within the organization. She believes that strong teams are built on trust, collaboration, and genuine care for one another, and she strives to create an environment where colleagues feel valued, supported, and empowered to succeed. Her commitment to mentorship and team development has contributed to both the professional growth of her coworkers and the continued success of the Tucson office.

Passionate about helping businesses and individuals find insurance solutions tailored to their unique needs, Melissa remains focused on contributing to the future growth of Shepherd Insurance throughout Arizona.

When she’s away from the office, Melissa enjoys spending time with her daughter, Taylor, and cheering her on in her passion for ballet and jazz at Ballet Rincon Academy of Dance. Her faith and family serve as the foundation of her personal life, and she remains actively involved in her church community and local non-profits. Melissa also loves escaping to Apache Lake on her boat to relax and enjoy Arizona’s natural beauty.

Regional Personal Lines Manager | Associate Partner

Amanda Hillhouse

Insurance Advisor | Associate Partner

Brad Morrow

Brad is part of a seasoned team of commercial insurance professionals serving businesses across Southwest Florida and beyond. Known for his energetic and enthusiastic personality, Brad is driven by customer satisfaction and consistently goes the extra mile to deliver top-tier risk management solutions. He helps clients shift their perspective—seeing insurance not just as a necessary expense, but as a strategic tool that supports long-term profitability and resilience.

After transitioning from a successful career as a PGA Professional to insurance sales in 2016, Brad quickly realized that his passion for helping others made the move a perfect fit. He holds a degree from Mississippi State University and brings years of sales and marketing experience to the table. As the lead advisor for the Golf and Country Club Program, Brad leverages his deep knowledge of the golf industry to provide tailored guidance, focusing on rate negotiations and coverage reviews that meet each client’s unique needs.

Brad began his insurance career in the Louisville, Kentucky, office before relocating to Sarasota in 2021. He is an active volunteer with Big Brothers Big Sisters of the Sun Coast, the local Chamber of Commerce, and the Rotary Club. Whether he’s building relationships on the golf course or giving back to the community, Brad is committed to making meaningful connections. He now resides in Lakewood Ranch with his wife of over 25 years.

Director of Corporate Training & Analytics | Associate Partner

Taylor Nikirk

Taylor Nikirk is the Director of Corporate Training and Data Integrity and an Associate Partner at Shepherd. Taylor joined the Shepherd team in 2015 as a Commercial Lines Account Manager with 14 years of experience in the Insurance Industry.

Taylor earned his bachelor’s degree in Risk Management and Insurance from Ball State University, providing a strong foundation for a career in the insurance industry. After transitioning into a corporate training role in 2018, he built and expanded Shepherd’s Training and Data team into a department of six who support the entire organization. In his current role, Taylor leads initiatives focused on employee development, operational excellence, and data integrity. He oversees the onboarding and training of new hires, supports acquisition teams through Shepherd’s systems and processes, and manages data integrity throughout acquisition conversions to ensure a seamless integration experience. His passion for developing people and improving processes has played a key role in supporting Shepherd’s continued growth and success.

When he is away from the office, you can find Taylor spending time outdoors, landscaping, flower arranging, and spending as much time with his nieces and nephews as possible.

Marketing Communications Manager | Associate Partner

Maryashly Sebastian

Insurance Advisor | Associate Partner

Wes Thomas

Wes Thomas is an Associate Partner at Shepherd Insurance LLC, where he focuses on commercial insurance placements for construction, contractor, and developer clients across Indiana and Kentucky. He specializes in structuring coverage for large construction accounts and risk transfer strategies for ground-up development and contractor operations, helping clients navigate complex exposures from project inception through completion.

Beyond his client work, Wes serves on the Junior Achievement of Kentuckiana board. Outside the office, he’s an avid golfer and coaches sports for both his sons, Zeke and Tucker.

Talent Manager | Associate Partner

Maggie Watkins

As Talent Manager and an Associate Partner, Maggie Watkins leads Shepherd Insurance’s recruiting and talent acquisition efforts. She oversees all phases of the recruitment process, partners with leaders across the organization to identify and attract top talent, and helps support employee engagement and onboarding across Shepherd’s 45+ office locations. Maggie also leads the agency’s internship program and serves as a key connection between Shepherd and university and industry partners.

Since joining Shepherd Insurance in 2022, Maggie has advanced into a leadership role overseeing talent acquisition and recruitment initiatives across the organization. Prior to Shepherd, she held roles in recruiting, operations, communications, marketing, and financial services. Maggie earned a Bachelor’s Degree in Organizational Communications from Ball State University with Minors in Marketing and Sociology, and received her MBA in Leadership from Butler University in 2026.

Outside of work, Maggie enjoys building relationships within the community and helping students and young professionals explore careers in the insurance industry. Personally, Maggie treasures time with family and friends, especially during Indiana summers spent together on the lake. Her impact at Shepherd has been recognized with the Rising Star Award in 2022 and the Ambassador of the Year Award in 2023.