WELLInspired™ Leadership

Meet CEO Joshua Ashby and his dedicated team.

Whether we are preparing your dinner, mowing the lawn or cleaning your home—at Fleet Landing, our staff knows that attention to detail is what makes the difference. Knowing names, tastes, hobbies and needs is not something that we like our staff to know. It is something they do naturally. Whether you are talking to a director, an aide or even our CEO Joshua Ashby, you will find that everyone—up and down our organization—is committed to one thing: giving you the kind of luxury retirement experience that leaves you with a full schedule and full of life!

Call 877.591.6547 or click here to schedule a visit and meet members of our staff in person.

Joshua Ashby
Chief Executive Officer

Joshua Ashby was named Fleet Landing’s chief executive officer in 2010.

He joined our management team in 2005 as Director of Health Care Services, responsible for the total operations at that time for our 80-bed skilled nursing center, Leeward Manor, our 80-bed assisted living facility, our home health agency and our physician’s clinic. In 2009, Josh was promoted to chief operating officer, managing the community’s day-to-day operations.

Josh is licensed by the state of Florida as a nursing home administrator and is an approved preceptor. He earned a bachelor’s degree in health sciences and a master of business administration degree from the University of North Florida.

Josh is Past Chair and currently serves on the board of LeadingAge Florida, a statewide association whose mission is to advance the possibilities for aging through service, education and advocacy. He also serves on the board of the World Affairs Council of Jacksonville and is a member of the University of North Florida Brooks College of Health Dean’s Advisory Council.

Cynthia Hack

Cynthia Hack oversees Fleet Landing’s business office and financial operations.

She is responsible for all accounting functions at Fleet Landing including accounts payable and accounts receivable, payroll and general ledger maintenance.

Prior to joining Fleet Landing in 2012, she served as the controller/financial officer for San Jose Country Club in Jacksonville.  She has also worked for Global and Diamond Support Services and The Jim King Companies.

A Jacksonville resident for more than 30 years, Cynthia earned a bachelor’s degree in accounting from the University of Florida and a master’s degree in business from the University of North Florida.

Patricia Mack
Senior Director of Independent Living Services

Patricia Mack offers a unique understanding of aging in place and the many ways to enhance independence and personal growth year after year. 

Prior to working in a senior living community, she took a sabbatical from corporate America to spend time with her aging mother. Her personal experiences sparked her interest in senior living communities and served as a driving force to serve people in their retirement years.

Patricia has demonstrated more than 25 years of progressive leadership in marketing, operations and sales management. Prior to joining Fleet Landing in 2007 as director of sales and marketing, she served as vice president of marketing and sales at Frederick Mennonite Community, a Pennsylvania-based continuing care retirement community. She has also served as vice president of marketing for Cherrydale Farms, a national fundraising company based in Pennsylvania, and as director of sales for Siemens USA, with headquarters in Boca Raton.

Elizabeth Sholar
Senior Director of Health Care Services

Elizabeth Sholar oversees the operation of our full continuum of care.

She directs the teams at Leeward Manor, assisted living, The Nancy House, memory care, a total of 100 beds and, our 70 bed skilled nursing facility, The Derfer Healthcare Pavilion, our home health agency and our physician’s clinic. Elizabeth joined our management team in 2000 and served as the administrator of our assisted living facility for eight years. She has a background in social services and extensive experience working with resident care and geriatric populations.

Prior to joining Fleet Landing, Elizabeth worked as a social worker in the senior community setting for four years. She also worked for a home health company, in community case management and for the Florida Division of Blind Services.

She is a graduate of the University of North Florida, where she earned a bachelor’s degree in psychology and masters of healthcare administration.

Olivia Bush
Director of Charitable Gift Planning

Olivia Bush develops organizational strategies and goals for Fleet Landing’s charitable giving efforts including major, planned, outright, benevolent, and scholarships.

She is an executive leader with extensive experience in sales, national and regional corporate leadership and non-profit management.Olivia develops and manages the Endowment Fund program to support Fleet Landing’s long-term priorities while helping donors accomplish their personal philanthropic goals.

Prior to joining Fleet Landing in 2012, she served as the director of development for First Light Maritime Society, which supports the St. Augustine Lighthouse and Museum. She has worked as the advertising director of the Jacksonville Business Journal, the publisher of the Ponte Vedra Recorder, the group publisher/general manager of Journal Community Publishing Group, the regional manager of Audio Visual Innovations and as a sales and advertising manager at the Florida Times-Union.

Olivia earned a bachelor’s degree in broadcast journalism from Southern Methodist University. She has attended the American Press Institute, which provides training, research and best practices for newspaper industry executives.

Olivia has received many honors and awards during her career. She is active in numerous civic organizations including Leadership Jacksonville, World Affairs Council, Cultural Council of Greater Jacksonville, Rotary Club, Planned Giving Council, JAX Chamber, St. Johns Chamber of Commerce and the Association of Fundraising Professionals.

Michele Holley
Senior Director of Human Resources

Michele Holley joined Fleet Landing as Senior Director of Human Resources on July 20, 2015, and brings with her almost 20 years of experience in human resources at the Director or Regional level, previously working for organizations such as North Shore Senior Center, Interstate Hotels & Resorts, and Swissôtel Hotels & Resorts.

Michele graduated cum laude from the University of Missouri-Columbia, where she earned a Bachelor of Science degree in Hotel and Restaurant Management, with a minor in both Human Resources and Sociology. Michele is certified as a Senior Professional in Human Resources (SPHR) through the HR Certification Institute. She was also awarded Chicago’s Regional Manager of the Year by the Illinois Hotel & Lodging Association.