Golf Staff

Terry O'Hara

Director of Golf

Terry joined the staff here at Longboat Key Club in September of 2009. He spent the last twelve years as Director of Golf at Cyprian Keyes Golf Club in Boylston, Massachusetts. During his time there Terry won many National and Local Awards. In 2007, Terry was awarded the prestigious “Golf Professional of the Year” by Callaway Golf. This award was something that he is most proud of accomplishing.

In addition, Terry was named "Club Fitter of the Year" by Callaway Golf in 2006, and named as one of the Top 10 Teachers in Massachusetts three times during the past eight years. He was recognized by Golf Digest in 2006 as leading one of the Top 5 Junior Golf Programs in the country. In addition, Terry has been named "Fitter of the Year for Ping" in Massachusetts, and is a certified fitter with Titleist, Cobra and Taylor Made.

In 2001, Terry was named “Merchandiser of the Year” for the New England Section for his skills with providing a top notch shopping and buying experience. In addition, he has served on the board with the New England PGA and is a past president of the Assistant’s Association.

Terry’s golfing skill has helped him win many numerous New England PGA Pro-Am events and is a past winner of the prestigious Tucker-Anthony Championship. He also won the NEPGA assistants Championship twice, was a past Massachusetts State Junior Champion and represented the United States in the Junior Cup Matches.

Terry brings a vast amount of experience in every area of the golf operation. He is excited to be part of the team at Longboat Key Club. Please feel welcome to call him at the Harbourside Pro Shop or stop by his office is located at the shop at Harbourside.

John Reilly

Director of Agronomy

John Reilly comes to us after three years at Sugarloaf Mountain Golf & Town Club in Minneola, FL as the Golf Course Superintendent. He started the project with designers, Ben Crenshaw and Bill Coore, from the ground up. Sugarloaf was highly acclaimed; it was ranked inside the top five in al the major golf publications. Currently, it is also ranked #3 in Florida “courses you can play” and is a perennial contender for top 100 modern courses in the nation.

Prior to Sugarloaf, John was Director of Maintenance at a multi-course facility (36 holes), Solivita in Kissemmee, Florida. There he finished the "grow-in" on the Cypress course post the three hurricane season. The Oaks Course at Solivita was designed by Ron Garl, allowing John Reilly to have hands-on experience maintaining Garl’s high flashed bunkers and “moving” greens much like here at Harbourside.

Before his position at Solivita, John Reilly grew-in The Legends and Diamond Players Club in Clermont, Florida. Prior to his “grow-ins” in Clermont he was the assistant superintendent at the Copperhead Course at Innisbrook, where he worked two tour events and participated in the course renovation.

John Reilly is a graduate of the Turf Program at Rutgers University in New Brunswick, NJ, where he specialized in soil science. He also holds a BA in English Literature and Psychology from Villanova University. His reputation in the industry is that of a “fixer”; at every stop, he has demonstrated the ability to turn projects into successes.

Barry Cheeseman

Director of Instruction

We're very proud to have Barry Cheeseman as our Director of Instruction here at Longboat Key Club. Barry has been playing golf seriously since 1986. He won the Florida State Amateur Championship and was Low Amateur in the Florida Open. Shortly after, he decided to turn pro and set the PGA Tour in his sights. Successfully securing a spot on his second attempt at the PGA Tour Qualifying tournament, he began his 18 year career of playing professional golf at the highest level. Playing almost 400 tournaments between the PGA and Tours, he amassed a combined 26 top 10 finishes, with a career best 3rd place finish on the PGA Tour and 2 wins on the Tour.

After spending two years working for the Houston Astros after his professional golf career, Barry decided to return his focus to teaching golf where he can bring his golf knowledge to the masses, teaching players of all skill levels from junior golfers to professionals that compete on tours around the world.

He resides in Sarasota with his wife Kerry. They have a son, Aaron, daughter in-law Laura, and two grandchildren, Addison and Jackson.

 Mark Anderson

  1st Assistant Pro - Links

Mark joined the staff here at Longboat Key Club as a seasonal associate in October of 2011. During the offseason, he was an assistant golf professional at Meadow Brook Golf Club, and Shining Rock Golf Club in Massachusetts. Mark came on board full time, as the 1st Assistant Golf Professional, in October of 2013.

Mark started his career in the golf industry working as an intern for the New England PGA. Mark spent three years with the NEPGA as an intern, and upon graduating from the University of Massachusetts, he began working full time for the NEPGA. It was there that he gained experience putting on top notch events, and credits his time with the NEPGA for his expertise in tournament operations. While working with the NEPGA, Mark developed a passion for teaching junior golf, and is an advocate for growing the game.

Mark is a Class A, PGA Professional, elected to membership in 2017. In addition to tournament operations, he enjoys teaching and fitting members and their guests.

Outside of work, Mark is a diehard Red Sox fan, and enjoys fishing and tennis. Mark cherishes the relationships that he has made with the members and guests, and always looks forward to building new relationships. If you haven’t yet introduced yourself, please call or visit Mark at the Links on Longboat Golf Shop.

 Jim Richard

  1st Assistant Professional - Harbourside

Jim joined the Golf Shop Staff at Longboat Key Club in October, 2015, and was promoted to 1st Assistant on October 1, 2017. He moved to the area on a full time basis after being a lifelong resident of Massachusetts and serving as the 1st Assistant at Franklin Country Club in Franklin, Massachusetts from 2013-2015.

Jim began his golf career in 2002 after being successful in the restaurant industry. He became a PGA Member in 2008 and learned his craft at some of the top clubs in the area. A highlight was his time at Pleasant Valley Country Club in Sutton, Massachusetts where the PGA held a tour event from 1969-1998. Jim is well versed in all areas of the golf business especially tournament operations, lessons, and club fitting and his goal is to help you enjoy your time here at Longboat Key Club.

Jim lives in Bradenton with his wife Elaine. They have a daughter Kate who attends USF in Tampa. When not at the club Jim is a Boston sports fan and likes fishing and travelling.

Mark Arnold

Golf Professional

PGA member for over 20 years. Lead instructor at Stow Acres in MA from 1994-1999. Director of Instruction at Cyprian Keyes in MA from 1999 to 2010. Director of Instruction at Blackstone National in MA from 2011 to present. Longboat Key Club instructor 2010 to present. Golf Digest award for Best Teacher in MA 2011-2012. New England PGA Teacher of the Year Central MA 2008.

Stephen Arnold

Golf Professional

Stephen is originally from Langhorne, PA. As an amateur, he won the Gold Association of Philadelphia's prestigious Patterson Cup and Silver Cross in 2006 as well as the Big 5 Intercollegiate as Philadelphia Cricket Club in 2007. After playing college golf at East Tennessee State and Villanova, Stephen moved to Florida in 2008 to play professionally. As a professional, Stephen won 3 times on the West Florida Golf Tour, before entering the PGA. Stephen worked as an assistant at Lakewood Ranch Country Club and caddied at the Streamstrong before focusing on his true passion of teaching in 2013. He is a PGA Class A member, elected in 2016. He looks forward to working with the members of Longboat Key Club and helping them reach their golfing goals. 

Jane Sirmons

Class "A" PGA Teaching Professional, Longboat Key Club - Golf Instructor

Teaching Professional Jane Sirmons is a Longboat Key Club favorite, a former LPGA Tour player, and a winner of Southwest Chapter’s PGA Teacher of the Year. As a former LPGA Tour player she knows how to properly train and show you how to get the most from your golf game.

Jane is originally from St. Petersburg, Florida. She loves working with members to peel strokes off their golf game and has been with Longboat Key Club since 1997. Jane played on the Futures Golf Tour, the European Tour and one US Open. Her lowest competitive round was a 65 and she has had 9 holes-in-one! When she's not playing golf and teaching, she loves kids, dogs, tennis and fishing.

Roberto Borgatti

Teaching Professional

Featured Teaching Professional, Roberto Borgatti, conducts golf clinics for players of all levels and leads seminars for teaching professionals around the world. Roberto coaches US & European tour players, up and coming juniors, golfers preparing for the PGA Playing Ability Test and executives of Fortune 500 companies. Roberto's teaching combines a proven method, golf-specific fitness and state-of-the-art video swing analysis. Roberto's international golf teaching assignments include the PGA of Sweden National, the Royal Club of Seville and Turnberry, Scotland. He is #1 rated golf pro for Crystal Cruises traveling to the world's most prestigious and exotic golf destinations. Roberto has appeared on the PGA Tour Network, Golf Digest’s Golf for Woman and Europe’s Canal + television. He is also a contributing editor for, and the author of A Swing You Can Trust, which British Open Champion Ian Baker-Finch calls “a golfer’s bible”. A Swing You Can Trust is available at our pro-shops on one Super DVD and an "enhanced eBook" series on iTunes.
To schedule a private session or playing lesson contact Roberto at (917) 678-1532

Mary Pearson

Retail Buyer

Mary grew up in Bridgeport, West Virginia where her family owned a grocery store. So she is no stranger to customer service and the retail world. After attending the John Robert Powers program for Apparel Buying and Merchandising, Mary spent eight years working as a Flight Attendant for U.S. Airlines. Life brought her to Florida 30 years ago. Her first position, after arriving here, was with Longboat Key Club in Tennis. She then moved on to work for Bath & Racquet and Edwin Watts in the Buying Departments for a total of 20 years. Four years ago, Mary returned to Longboat Key Club as the Golf Retail Buyer. She passed on her passion to her daughter, Stacy, who now travels the country working for Michael Kors. When not greeting Members and guests with her outgoing personality, Mary loves enjoying the wildlife and natural beauty of Florida.