Management Team

General Manager/
Chief Operating Officer


Joe is originally from Chicago, Illinois and relocated to Naples in 2001.  He has spent a majority of his career in Florida working for WCI Communities, a Florida based housing developer. During his time with WCI he had the privilege of working at some of the most exclusive communities on the west coast and east coast of South Florida. During Joe’s tenure with WCI, he was directly responsible for The Colony Golf & Bay Club, Westshore Yacht Club, Pelican Preserve Town Center, The Club at Pelican Preserve, Club LaMorada and Arborwood Preserve. He indirectly assisted with operations at Tuscany Reserve (now Talis Park), Parkland Golf & Country Club and Old Palm Golf Club.
Joe has a strong background in food and beverage, and over time he's held positions as Food and Beverage Director, Club Manager, Corporate Food and Beverage Director, General Manager and Regional General Manager.  

In May of 2017, Joe was directly recruited by the CEO of Shell Point Retirement Community, the second largest continuing care retirement community in the country. Joe held the position of Senior Director of Hospitality overseeing all hospitality operations for this large 2500 resident community. Shell Point has a 50-year history and Joe was charged with enhancing the lifestyle for its 2,500 residents who enjoy 11 dining venues, a resident life/activities department, racquet sports, a 40-room hotel, marina, 18 hole golf course and onsite transportation—all of which where operated by nearly 400 employees under Joe’s leadership.

Joe has been married for 12 years to his wife, Jennifer, and they have a 6-year-old daughter, Emma. They enjoy the pool, beach and travel. Joe and his wife are both fitness enthusiasts and Joe’s interests outside of work are photography, music and art. He also enjoys writing on various topics, mainly leadership.



Assistant Controller

239-353-1780 Ext. 105

Jennifer is a South Florida native from Miami, FL who studied accounting at Florida International University. She married Kyle in 1996 and they moved to Naples the day after they returned from their honeymoon to Naples, Fl. They have a 15 year old son, Colton, who plays football for Naples High School. She has been in the local country club industry for 8 years, prior to that she worked at a land development consulting firm. Jennifer is an active member of Hospitality Financial and Technology Professionals (HFTP).

Her hobbies are fishing, boating, and enjoying the beautiful Naples waters and beaches. Jennifer joined the Countryside team in 2016.


Facilities Engineer

239-353-1780 Ext. 119


Cody grew up in Novato, California and moved to Florida in 1989. Since being in Florida he has continued his security and audio visual trade. His past work experience included subcontracting for the FBI and the United States Secret Service providing security and I.T. services.

He joined the Countryside team in June 2018 as our Facilities Engineer. Cody oversees inside maintenance and house keeping.

In his spare time, he enjoys to kayak fish while exploring the great outdoors.


Director of Communications

239-353-1780 Ext. 106

Mary grew up in Fort Myers, Florida. She graduated with a BS degree in Business Communication and has over 30 years experience in the fields of marketing and communications. Prior to joining the Countryside team, she worked as a Marketing Director in the Fort Myers area for private businesses whose overall capital increased due to her marketing campaign leadership. She is proficient in graphic design, advertising, public relations, presentations, and conference event planning materials. She has a vast amount of experience in designing and implementing a variety of media platforms for business branding and promotions utilizing traditional products - print publications, radio, television, as well as websites and social media outlets.

She joined the team of Countryside professionals in 2007 as our Director of Communications. Mary works as the liaison between club management and members. She continues to build our community's communication needs with our website, weekly informational emails, club brochures and newsletters, promotional flyers and advertisements, annual directory, membership surveys, and various other promotional materials. She looks forward to her continued work of enhancing our overall community communications and strives to improve the club's image to the general public. 

In her spare time Mary and her husband Jay enjoy spending time doing outdoor activities together, as well as traveling and spending time with their children and grandchildren.


Director of Food & Beverage

239-353-1780 Ext. 144

Kevin grew up in Troy, Michigan. He has lived in Fort Myers, Florida for since 1988. He has over twenty eight years of experience in Food and Beverage, most notably with The Colony Golf and Country Club, Sanibel Harbour Resort and Gateway Golf and Country Club.

Kevin is a proud parent of his daughter Kaitlyn, 22 and Sam, 19. He enjoys golfing, working out and watching hockey. He looks forward to building upon the many successes within our food and beverage operation.



Executive Chef

239-353-1780 Ext. 145

Jay brings 20 years of culinary experience both as a restaurateur and Executive Chef of clubs on the East Coast such as Hobe Sound and Hawk’s Nest. For the past 5 years Jay has been the Executive Chef of Pelican Preserve Town Center. In his tenure there he’s managed increased activity levels as the community grew from 900 homes to nearly 2000 homes. Jay excels in member relations and managing the desire for trendy menu variations while maintaining a level of comfort for longer-tenured residents. In addition, he served on the executive team when the community performed a study and launched a series of multi-year renovations and amenity expansions notably a new poolside restaurant.

We’re excited for Jay to join our team and bring a fresh set of eyes to the dining component of Countryside.



Financial Manager


Jeff Jacob, Chief Financial Officer. Jeff has a Bachelor’s of Business of Administration degree from Western Michigan University with a major in accounting. Jeff also studied at the University of Miami, Coral Gables, and has over 20 years of professional accounting experience that includes previous stops at the Bureau of National Affairs, Kiplinger Washington Editors, and Clubessential.

Prior to moving to Naples and joining the Countryside team in 2005, Jeff spent his professional career in the Washington DC area. Jeff’s primary role at Countryside is management of all financial aspects of the Association, including internal and external reporting.

In Jeff’s time away from Countryside, he enjoys traveling and boating.

Master Professional
Director of Golf

239-353-1780 Ext. 121

Stephanie grew up in upstate New York. She played junior golf, high school golf, and collegiate golf in the Albany- Saratoga area. She earned a Bachelor’s of Science Degree concentrated in Finance from Siena College, and shortly after she headed south to Florida. Initially moving south for a seasonal assistant golf professional position at Vanderbilt Country Club, she quickly realized that she loved the area and wanted to make Southwest Florida her permanent home. She worked at as Assistant Golf Professional at Hammock Bay, Bear’s Paw Country Club, Island Country Club and Countryside Golf and Country Club from 2003-2013. In that time, she earned her PGA Class A Membership.

In 2013, Stephanie went on to continue her PGA education and became a Certified PGA Member, specializing in Golf Operations. This is a credential that roughly 3% of all PGA members have achieved. In 2014, Stephanie was hired by ForeGolf Partners into a duel position of General Manager and Director of Golf at River Hills Country Club, located east of Tampa. After almost one year in central Florida, she was delighted at the opportunity to come back to Countryside as Director of Golf. In 2017 Stephanie became a PGA Master Professional, this is the highest level of education the PGA offers. At the time, she was one of five women in the country to have earned this title.

Away from work, Stephanie enjoys golfing and socializing with friends, spending time at the beach, and cheering on her favorite New York sports teams.


Director of Human Resources
Executive Assistant

239-353-1780 Ext. 103

Deb is originally from Bethlehem, Pennsylvania and relocated to Naples in 2012. She graduated from Cedar Crest College with a Bachelor’s of Social Work and from Marywood University with a Master’s of Social Work. She worked for the majority of her career at St. Luke’s Health Network in Pennsylvania as a case manager in areas of Trauma, Critical Care, and Palliative Care before relocating to Naples. Prior to joining Countryside in May 2019, she worked at Bentley Village and The Arlington of Naples as Director of Resident Services. She was responsible for resident access to services along the continuum of care as well as concierge, security, guest house, and social work services. Most recently, she developed and implemented a new Resident Engagement Program at Shell Point Retirement Community and served as the Resident Engagement Manager.

Deb is married for the last 25 years to her husband Tom. She enjoys running, beach, and spending time with her family and friends.



Wellness Center Director

239-353-1780 x 172

Tara was born and raised on Long Island, New York and moved to Naples in 1995. A former college athlete, she has not lost her love for fitness and exercise. Before joining the Countryside team in August of 2017, Tara worked in the Real Estate, Home Health Care and fitness industries. She has been a personal trainer since 2012 with a certification from the American Council on Exercise (ACE) and is a certified Spin instructor. She enjoys working with clients to help them reach their personal health and fitness goals. Tara has been married to her high school sweetheart Billy since 1995 and they have three children – Hannah, 21, Joseph, 19 and Samuel, 12. Tara enjoys the beach, working out and traveling with her family.

Tara is excited to be a part of the Countryside team as the Wellness Center Director and strives to help every member improve their fitness level, regardless of age, skill or limitation. Her goal is to encourage members while helping them to feel strong and confident in their ability to stay active and enjoy a healthy lifestyle.



Golf Course Superintendent

239-353-1780 Ext. 151

Born in Tampa, Florida J. D. and his wife Debbie moved to Naples in 1994 as the assistant superintendent at Wyndemere Country Club. He then became the superintendent at Imperial Golf Club’s West course, and later rebuilt the East course. He then became construction superintendent at Arrowhead Golf course and stayed for 2 years after completion. He accepted the position here at Countryside in November 1999.

He has been a member of the Golf Course Superintendent’s Association of America for 26 years. On February 26, 2004 J. D. earned the designation of Certified Golf Course Superintendent for having met standards of proficiency through experience, education, testing and performance in the profession of golf course management. He is also a member of the Florida Golf Course Superintendent’s Association and earned a certificate for Best Management Practices. He is a member of the Florida Turf Grass Association, and has an A. S. Degree in Golf Course Operations. J. D. wants to use this knowledge to be a team leader, and a team player on Countryside’s Professional staff.

JD's goal is to serve the members and guess' with good golf course playing conditions and aesthetic beauty throughout the community.

He enjoys playing golf, fishing, and spending time with his family.