Qualifications

H. Roller Shipplett, Jr.
Managing Director
rshipplett@investdavenport.com

Roller joined Davenport in November 2024 after 48 years as a Financial Advisor with Truist (formerly BB&T Scott & Stringfellow). He began his career in 1976 after working for his family’s business and practicing as a CPA in Winchester, Virginia. He graduated from Bridgewater College with a Bachelor’s degree in Business Administration and Accounting. He is Series 7, 63 and 65 registered with FINRA.

Active in the community, Roller has served as a Trustee of the Staunton Augusta YMCA for 40 years. For the past 15 years he has served on the community advisory board for Heifetz International Music Institute. He is also a member of Covenant Presbyterian Church. Roller and his wife, Jerry Lynn, have two adult children, two grandsons and one granddaughter. Outside of work, he enjoys traveling, reading mystery and history books, and collecting U.S. coins. He owned and toured a 1935 Packard Convertible Dietrich Victoria automobile for 34 years. 

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Jakki Avery, CFP®, CRPC®, APMA®
First Vice President-Investments
Financial Advisor

javery@investdavenport.com

Jakki joined Davenport in November 2024 after six years as a Financial Advisor at Truist. Prior to becoming an advisor, she was a Registered Client Service Associate for six years and a math teacher in Augusta County Public Schools. Jakki earned a B.A. in English from Hollins College and a B.A. in Mathematics from Mary Baldwin College. She is Series 7 and 66 registered with FINRA and licensed to offer long-term care and life insurance and annuities. Jakki is a CERTIFIED FINANCIAL PLANNER (CFP®), a Chartered Retirement Planning CounselorSM (CRPC®) and an Accredited Portfolio Management AdvisorSM (APMA®).

Jakki is active in the community and currently serves as the Treasurer for the Glenmore Hunt Club and the Glenmore Foundation. She is a Sunday school teacher and serves on the finance committee for Memorial Baptist Church. She and her husband, Alex, have two sons. In her spare time, Jakki enjoys foxhunting, trail riding, camping, traveling, reading and spending time with family. 

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Alicia L. McAnney
Client Service Associate
amcanney@investdavenport.com

Alicia joined Davenport in November 2024 after serving as a Client Service Associate at Truist for one year and a Senior Relationship Banker for four years. She provides administrative and operational support for the Shipplett-Avery Group. In 2022, her branch at Truist was chosen as the Top Lending Branch and earned the 2022 Purpose Recognition award.

Alicia graduated from Star Technical Institute with a certification in EKG Technology and Phlebotomy. As a Military spouse of 23 years, she served as an Ombudsman for the US Navy. In her free time, she takes pride in serving her community as an Awana Leader. She and her husband, Christopher, have four adult sons and one teenage son. She likes exercising and getting outdoors hiking and fishing, and recently started hunting with her husband. She also enjoys baking, reading, and visiting wineries and small towns.

Katie Bosserman
Client Service Associate
kbosserman@investdavenport.com

Katie joined Davenport with the Shipplett-Avery Group in November 2024 after serving as a Client Service Associate at Truist for 19 years. As an integral member of the team, she assists with client service requests and processing and monitoring new accounts. Katie also handles the reception desk for the Staunton office.

She graduated from Radford University with a degree in Journalism. Outside of work, Katie currently serves as the Clerk of Session at Tinkling Spring Presbyterian Church. She and her husband, Matt enjoy watching college sports and cheering on their son, Tucker at his baseball games. She also enjoys reading and spending quiet time at the beach with friends and family.