Our Team

The ONSHORE Team

The ONSHORE team are the women and men who work together in the Company’s headquarters offices in Ft. Myers, FL, alongside our intrepid founders Steve and Doris Colgate. From managing finances, to sales and marketing, and keeping all the systems going, they gather daily and weekly to insure success at all levels of the company.

The OFFSHORE Team

From the day Steve Colgate opened his first school in Manhattan in 1964, he has insisted on sailing instructors with a passion for sailing and boating, excellent teaching skills, extensive sailing knowledge and experience in small and large cruising and racing boats. The OFFSHORE Team are men and women chosen for all of the above plus humility, patience, dedication to you (our clients) and loyalty to Offshore Sailing School (the company).

If you would like to join our team, please see Employment Opportunities.

“Anyone who is looking for a top-notch, unforgettable, hands-on experience should take an Offshore Sailing School course! Our instructors were Amazing!! They were incredibly patient, encouraging, knowledgeable, positive, helpful, professional and CALM! We were impressed with the variety of teaching techniques used to make learning fun and interesting for us both. The Fast Track To Cruising course exceeded our expectations in every way.”

Scott & Sharon Rutherford

Thamesford, Ontario
OSS 101/103/104 - Fast Track® to Cruising

Onshore Team

Steve & Doris Colgate

Chairman (Steve), President & CEO (Doris)

The Colgates inspire all of us to give 110% to the art of teaching sailing. Their passion for delivering the best on-water education in fun settings started in 1964 when Steve Colgate founded Offshore Sailing School in New York City. On the recommendation of her then employer Yachting Magazine, Doris Colgate met Steve while taking a Learn to Sail and then Racing course at Offshore Sailing School. The rest is history. Read their complete story and the reasons for their dedication to sailing here.

Dana Matthews

Executive Vice President & Chief Financial Officer

Dana is responsible for all the company’s financial functions including accounting, corporate finance, banking, and corporate growth; in addition to overseeing  and managing human resources and payroll activities. Her career spans 30 years of experience in financial management, business leadership, and corporate strategy and growth. Dana holds a Bachelor of Business Administration and Accounting from George Mason University. In her spare time she enjoys Florida’s many beaches, boating, cruising, traveling, spending time with her family and dog, and now sailing.

Beth Oliver

VP and Director of Sales & Marketing

Beth has more than 25 years of experience with large corporations and entrepreneurial businesses, including Hiram Walker/Allied Domecq, General Motors and its automotive brands, The Walt Disney Company, Warner Bros., film and television production. Beth managed automotive relationships with the Olympic Games, MLB, NASCAR, Country Music, celebrity endorsements, and sponsorships. Her team at agency Campbell Ewald in Detroit executed more than 3,000 event days a year. After relocating to Southwest Florida with her husband in 2010, Beth managed sponsorships for the thought-leader Imagine Solutions Conference in Naples, and owned her own marketing services consulting business. Beth was elected to the Sail America Board of Directors in 2023, and previously served as a Board member for CHEF: the Culinary & Hospitality Education Foundation of Southwest Florida, and on the Advisory Council of the Southwest Chapter of the Leukemia & Lymphoma Society.

Josh Julow

Director of Revenue Generation & Logistics

Josh Julow relocated to Florida in 2014 from the Midwest, trading fresh water for salt water. He grew up in the Metro-Detroit area and spent a decade in Milwaukee after attending Marquette University for Secondary Education. Growing up in the Great Lakes area, time on the water was always a part of Josh’s life. He spent over 6 years at Offshore Sailing School starting as the Sales and Marketing Intern before eventually shifting his focus to operations. Having spent 2 years away from Offshore at Rice Windows and Doors as a Production Manager during the Covid pandemic Josh was delighted to return to the sailing industry at the end of 2021, saying “It is more enjoyable to sell people their dream lifestyle as opposed to a dream home.” Now, as Director of Revenue Generation & Logistics, Josh brings innovative ideas and leadership to Offshore Sailing School. When not on the water, he spends free time moderating the largest ice hockey forum in the world, and taking advantage of Florida weather, playing golf and enjoying time on Florida’s many beaches.

Diana Smith

Sales Associate

When her two sons left the nest, Diana elected started sailing on Highlanders in Indianapolis, IN. In 1997 her General Motors job moved to Detroit where she raced on a C&C35, J120s and NA40s at Bayview Yacht Club – one season as skipper and seven seasons as crew chief. She has sailed “her favorite boat,” the Colgate 26, since its introduction in 1997 and has taken every course Offshore Sailing has to offer. During her four years as President of the National Women’s Sailing Association, she taught at Women’s Conferences, led Caribbean flotillas and Chesapeake schooner sailing programs. Diana joined Offshore in 2004.

Jill Harwood

Sales Associate

Jill grew up on the waters of Lake George and Saratoga Springs, NY. She has worked in Sales and Marketing for 20 years. As a recent empty nester, Jill realized that you must move yourself and your dreams to the front of your priorities. After years of selling for companies looking for financial gain, she was drawn to Offshore Sailing to be able to provide people with the opportunity to live their passions and dreams of sailing, and not put off the good stuff to focus on the daily grind and what everyone else needs from us. She often can be heard saying, “if not now, when?” Jill’s hobbies include, competitive darts, crafting, refurbishing furniture, boating and stand-up comedy.

Cheryl Jones

HR and Finance Specialist

Cheryl is a Navy daughter and a Navy wife.  She grew up on Maryland’s Eastern Shore and Southeast Virginia and has always loved being around waterways. When her husband left the Navy, they moved to the Roanoke Valley and they would have to plan trips to visit friends and family in order to get back to the water. When Cheryl’s husband accepted a job with a major commercial shipping line, it allowed them to move wherever they wished, and they happily settled in Southwest Florida, where family and Cheryl’s water awaited. Cheryl enjoys spending time on her lanai, enjoying the views and reading books.

Rebecca Matthews

Operations Project Manager

Rebecca is a 2023 graduate of Christopher Newport University in Tidewater Virginia, where she studied mathematics. While new to the sailing world, it didn’t take long for her to enjoy being out on the water. In addition to sailing, she enjoys other water-based activities. Growing up she swam competitively for nearly ten years, and now likes to go boating and taking advantage of Florida’s beach weather. In her free time her hobbies include reading, singing, knitting, and crochet.

Offshore Team

David McCormick

Fleet Maintenance Manager

Dave brings over forty years of knowledge on marine and commercial equipment and systems to Offshore Sailing School, as our Fleet Maintenance Manager. His background includes service in the USMC and the USCG, retiring with over twenty-three years of USCG service as Machinery Technician Chief Petty Officer. He utilizes his diverse background and experience to ensure our vessels are kept in tip top shape. Interesting trivia on Dave, he is our Square-Rigged Sailor, having sailed on the USCG Cutter Barque Eagle (America’s Tall Ship) in 2001 as a crew member and instructor on engineering and damage control to Officer Cadets from the USCG Academy in New London, CT. When not working he is an avid outdoorsman and can be found in the woods or on the water.

Mark Walker

Mark is a seasoned US Sailing Instructor with over a decade of experience sailing across the Caribbean and Gulf Coast waters. Adhering to the highest standards of safety, instruction, and seamanship, Mark excels in hands-on training and effective communication, with a career featuring multiple Caribbean deliveries, enhancing his sailing expertise and appreciation for the region’s unique challenges. An advocate for marine conservation, Mark emphasizes the importance of preserving ocean ecosystems in his teaching; and possesses comprehensive knowledge of marine mechanics and vessel maintenance, ensuring preparedness for any maritime adventure. His teaching approach focuses on creating a supportive and empowering learning environment for sailors of all skill levels. Eager to share his passion for sailing, Mark looks forward to embarking on new adventures with students, aiming to create lasting memories while fostering responsible maritime practices. His versatility as an instructor makes him an invaluable asset to Offshore Sailing School and a trusted guide for both novice and seasoned sailors.

Art Hansen

Art has been sailing since he was two years old. In his youth, he cruised and raced with his family on the Chesapeake Bay in Maryland. He also spent one summer working as an instructor at the Annapolis Sailing School. After serving 4 years as a US Army Infantry Officer, he moved to Florida. He currently cruises extensively along the West coast of Florida with his wife and First Mate (Yellow Lab named Barney). After spending 32 years working in manufacturing, he decided to leave corporate life and become a sailing instructor. He currently holds an OUPV Captain’s License and works out of the St Petersburg location.

Trevor Burnett

Instructor

Trevor is a 7th generation Floridian who has been on boats since before he could walk. He began sailing with his father when he was five and has put in his fair share of time on the water, from sailing the tropical waters of the Caribbean to the cold, icy waters of the Greenland fjords.  Trevor loves sharing his knowledge with everyone he encounters, especially as an instructor for Offshore Sailing School. He believes in putting extra emphasis on self-sufficiency on the water so you can be prepared for anything when you are out in the ocean away from the nearest boatyard. When not working professionally with Offshore Sailing School, Trevor spends his free time fixing up and cruising on his own sailboat in Florida’s Tampa Bay area and beyond, and invites those who want to learn sailing and cruising to join him for a relaxing and informative week on Florida’s beautiful coastline.

Randon Finkelstein

Director of Sailing & Boating

Randon is from Houston, Texas where he learned to sail at age 12 in the local lakes and the Gulf of Mexico. He is a member of the prestigious US Sailing National Faculty and a certified US Sailing Keelboat and Cruising instructor in all levels from Basic Keelboat through Passage Making. He also holds other licenses and certifications including: USCG 6 pack , RYA Yachtmaster Offshore, marine diesel engineering, and advanced open water diving. He has sailed across the Atlantic from  Portugal to the Canary Islands and then to Antigua; and in Tahiti, Nova Scotia, The Florida Keys, Belize, Turks and Caicos, and The British Virgin Islands.

Folkert “Dutch” Jongkind

Caribbean Regional Manager

Born and raised in the Netherlands, sailing was an obvious but casual hobby for Folkert. In 2006 he turned his hobby into a fulltime profession. He began teaching sailing on the Solent on England’s south coast, and seasonal work took him all over Europe and the Caribbean. He spent a year in the British Virgin Islands, went back to the Solent to teach there for two more years, and did a lot of deliveries in the Bay of Biscay, English Channel and Atlantic Ocean. The BVI beckoned with sunshine, good wind, great people, and a great opportunity to work with Offshore Sailing School! Dutch holds Royal Yachting Association and US Sailing instructor certifications. He began working for Offshore Sailing School as an instructor in 2014 and was promoted to Senior Instructor and Caribbean Regional Manager in the British Virgin Islands in May 2018.

Cheyenne Warner

Senior Instructor

Cheyenne grew up on the island of Antigua where he started sailing when he was 3 years old. He learned on small boats at the local yacht club, and in his teens became a sailing instructor there. At 17 he was introduced to ocean racing, took Royal Yachting Association classes, and became a charter and delivery captain which led him to sailing all over the Caribbean, Europe and the United States. Cheyenne is a U.S. citizen and holds all levels of US Sailing Instructor Certification, as well as a variety of Royal Yachting Association and Maritime Training Certificates.

George Samalot

Senior Instructor and Colgate 26 Project Manager

While working at Ulmer Sails on City island, NY in 1976, George taught part-time at Offshore Sailing School on City Island. That Fall he joined Offshore full time at its year-round location on Captiva Island, Florida. A year later went back to Offshore on City Island NY and then to the British Virgin Islands to open an Offshore Sailing School branch there. After a long career delivering yachts, sailmaking, and running his own company Samalot Marine for 35 years, George and his wife, Barbara, moved to SW Florida where he joined Offshore Sailing School to teach sailing, again. An avid racer, he has sailed multiple times in the Newport-Bermuda Race, the Southern Ocean Racing Circuit, many distance races on Long Island Sound, was on the US Admirals Cup Team in the 1987 Fastnet Race, and did the Miami-Montego Bay Race in 1989. A racing association leader and volunteer, George received the Ned Anderson Trophy from YRALIS for “Outstanding Service to Yacht Racing” on Long Island Sound in 2012. He holds a US Coast Guard 200-ton Masters License with sailing endorsement and US Sailing instructor certifications; and is project manager in updating and building the Company’s Colgate 26 keelboats.

Andrew Deen

Instructor

Andy’s love of naval history ultimately led him to try sailing lessons, and he was hooked! He and his wife Kathryn joined a sailing club and have cruised up and down the west coast of Florida, as well as throughout the Virgin Islands. Andy loves sailing so much that he decided to change careers and teach sailing full-time. He holds the USCG 25-Ton Masters license with sailing endorsement and instructor certifications. Andy says he is excited to share his sailing passion with Offshore Sailing School clients, and hopes that all he teaches leave the course with newfound confidence to charter a sailboat anywhere in the world!

Jaime Torres

Instructor

Jaime was born and raised in the warm tradewinds of Puerto Rico and has spent over 50 years sailing all over the world on everything from windsurfers to maxi yachts. His dad started him as crew on a C&C 41 in the early 70’s. When he was just 12 years old, Jaime did his first delivery from Annapolis to San Juan, PR. Since then, he says he has never stopped sailing in one form or another and has rarely been more than a few minutes from the water. “Sailing is my greatest passion,” says Jaime. “I spend every free second racing RC boats, wingfoiling, or organizing racing in my sweet Melges 24 in the local fleet or around the US.” Jaime gets immense satisfaction from improving people’s recreational and racing experiences in St. Petersburg, Florida. “I love my work as a sailing instructor, delivery, and charter captain, but one of my favorite jobs is serving as the Race Manager for Antigua Sailing Week. It brings me back to the Caribbean every year, where I reconnect with my sailing roots.”

Kelly Davis

Instructor

Kelly grew up in Texas and studied computer science in Colorado. He has taught live aboard courses extensively, sailed all over the Caribbean, Belize, Cozumel to San Pedro and the British Virgin Islands. For many years, Kelly raced Hobie Cats and ran a dive shop in the Florida Keys. He holds a USCG 50 ton license, US Sailing Basic Keelboat and Cruising instructor certifications, and is a PADI open water scuba instructor.

Patrick Najou

Senior Instructor

Patrick holds all levels of US Sailing instructor Certification: Basic Keelboat, Basic, Cruising, Bareboat Cruising, Coastal Passage Making, Performance Sailing Catamarans, Power Boats and Coastal Navigation and holds a USCG Master 50 Ton license. Born in France, Patrick spent several years teaching sailing in Brittany, then in Los Angeles and Seattle. He has over 30 years of sailing experience, from small crafts to offshore cruising and is a full-time instructor for Offshore Sailing School in the British Virgin Islands.

Elin Sandberg

Instructor

Elin has lived and sailed all over the world, and is enjoying a change from the frigid North Atlantic and Irish Sea to the much warmer waters of the British Virgin Islands. She is an RYA Yachtmaster and loves sharing her passion for sailing on boats large and small. Coaching and mentoring female sailors and skippers is particularly important to her, as well as making a vacation, life or career on the water accessible to everyone. When she’s not teaching sailing, Elin can be found offshore racing or on long ocean passages while perfecting her celestial navigation skills.

Andy Ryner

Florida Fleet Technician

Andy sailed for more than forty years on the great lakes, and has sailed in Florida since moving here in 2012. He has raced on various sailboats in a variety of competitions including several Port Huron to Mackinac Races and Chicago to Mackinac Races, as well as weekly yacht club races. Andy has a degree in Mechanical Engineering and holds Marine Mechanic Certification.

Daniel Jackson

Instructor

Originally from England, Daniel found his love for sailing when he moved to the Pacific Northwest in 2011. He and his wife Klaudia have owned several cruising sailboats and explored the expansive waters around Seattle and Puget Sound for the last decade. Daniel is also an avid racer. He sailed for his local club in Olympia, WA during the last 6 years while delivering yachts up and down the west coast in his spare time. Daniel has held a USCG OUPV (6 pack) license for the past 5 years and recently upgraded to a 25-ton Masters License. He relocated to Florida full time where his passion for sailing and teaching continues. Daniel looks forward to exploring the waters and assisting you in reaching your own sailing goals, whether that’s learning how to sail, owning, or chartering a sailboat or just having a great time out on the water.