Directors
Jesse Winter: President & CEO
Coach Jesse Winter started his basketball career at South Side High School where he was a 2-year captain and a standout player. He was inducted into the program’s Hall of Fame for his achievements of being All-Long Island and leading the team to the Nassau County Championship Games. After high school, Jesse played at SUNY Cortland where he was a 2-year Captain. For the Red Dragons, he graduated as the All-Time Leading Career Scorer record in the school’s history scoring 1,525 points, was 2nd All-Time in assists and a 2-time All American that helped lead the team to a SUNYAC Championship that advanced to the 2nd Round of the NCAA Tournament. After College, Jesse played 1 season of professional basketball in Israel in the National League for Ramat Hasharon. Jesse is currently a FIBA Certified basketball trainer. He was the Basketball Director at Camps such as Camp Wayne, Coalman Country and the Junior Knicks Virtual Summer Basketball Camp. In 2021, he coached our 5th Grade Team to an AAU D2 National Championship in Orlando, Florida. In 2024, he coached our 8th Grade Team a Nike – Balling On The Beach National Championship in Fort Lauderdale, Florida.
Jesse was recently named the AAU Boys’ Basketball Advisory Committee Chair nationally and internationally. While continuing in his role with Level Up LI he will lead this advisory committee of key basketball stakeholders who have extensive knowledge of basketball operations to aid in the growth and development of AAU Basketball Programs. AAU President Joe Mirza, who formed the committee, is who Jesse will be reporting to along with Jim Fox who is an AAU Board member and Special Advisor to the to President Mirza. The announcement read as follows:
“Winter has an extensive basketball pedigree having been named to both his high school and college Hall of Fames. While attending SUNY Cortland, he became that college’s All-Time leading scorer, a record that was held for more than 10 years. Eight years ago, Winter founded Level Up Long Island, an AAU program that has grown to sixty (60) boys’ and girls’ teams ranging from 2nd through 12th grades. All skill levels are represented at Level Up Long Island, providing participation opportunities for athletes from beginner to elite abilities.
“There is virtually no one who has more knowledge about what is going on in Boys’ club basketball right now than Jesse Winter,” said Jim Fox, AAU Board member and Special Advisor to the President for AAU Basketball. “We are excited to welcome Jesse Winter to the new advisory committee. Mr. Winter is dedicated to the growth of AAU Basketball and will be a great asset to our organization.”
Trevor Stark: Boys Basketball Director
Coach Trevor Stark started his basketball career at Robert F. Kennedy High School where he was a 2-year Captain. He was the school’s All-Time Leading Scorer and finished 2nd All-Time in assists. He then attended Hilbert College in Buffalo, NY, where he was 1st Team All-Conference in his Junior year and 2nd Team All-Conference his Senior year. He capped his Hawk career with 1,245 points and the 8th highest All-Time scorer in the school’s history. He also helped lead the team to its first regular season conference championship. He finished 1st All-Time in free throw percentage and 2nd All-Time in assists. In 2025, Trevor was inducted in the Hilbert College Hall of Fame. After college Trevor played 3 seasons professionally in Israel for Hapoel Tzfat and Hapoel Maboaim.
Nikko Callender: Boys Middle & High School Director
Coach Nikko Callender starred at Baldwin HS where he was a 2-time All-County player. From there he played at Concordia College as a 3-year starter. He became one of a select group of student-athletes in school history reaching the 75 plateau in every major stat category — blocks, steals, points, rebounds and assists. After College Nikko began coaching at Mineola HS winning JV Conference Coach of the Year. He then joined the Baldwin HS coaching staff where he twice won JV Conference Coach of the Year and produced a record of 48-9. For 2 years he was the Assistant Coach of D2 NYIT and Queens College. Last year he was the Head Coach for LuHi’s Varsity Regional team which he helped lead to a conference championship. He was also the Athletic Director and Basketball Head for Camp IHC in Pennsylvania. Currently, he is the General Manager at our program affiliate the Hoop Lab.
Ashley Jackson: Girls Middle School Director
Coach Ashley Jackson started her basketball career at Amityville Memorial High School where she was a 4-year starter. From there she went to Nassau Community College where she continued her education and basketball career then transferred to York College of Pennsylvania where she completed her college career. After College she began coaching at Nassau Community College for 2 years as the Assistant Head Coach for the Women’s Basketball Team where she helped build the foundation of a strong program. Ashley was previously the Head Girls’ Varsity Basketball Coach at Amityville Memorial High School. She spent 2 seasons with Five Towns College as the Assistant Coach and is now heading into her first season as the Head Varsity Coach at Lawerence Woodmere Academy. Ashley is also a clinician with the Long Island Nets G-League team.
Brad Weiss: Boys Elementary School Director
Coach Brad Weiss started his basketball career at Plainview JFK High School. He was a 3-year Varsity starter, a captain his senior year and racked up awards such as All Conference and All Long Island. Coach Brad was also a member of LongIslandBasketball.com’s Honor Roll of top LI high school basketball players. He went on to play for D3 St. Joseph’s College in Long Island. He was a 3-year starter at D3 SJC where one season he was 3rd in the Skyline Conference in blocked shots and ranked towards the top in SJC school history in blocked shots. Coach Brad has experience coaching and counseling players of all ages for the NCPAL. He is also involved as a clinician for the Long Island Nets for all age groups. This year was his 5th season as the JV Basketball Coach at Plainview JFK High School. This year he received Conference Coach of the Year honors.
Chris Coalmon: Director of Player Development
Coach Chris Coalman started his high school career at St. Mary’s for 2 years where he played major minutes and helped them get to the Catholic School Championship and Semifinals on Long Island. He transferred to LuHi as an upperclassmen and was named 1st Team All-Long Island and All-State as a senior. He capped his career scoring 1,500 points. He received a D1 scholarship to play at Robert Morris and after 2 years transferred to Adelphi University where he was a star player for the team. Chris was the Graduate Assistant at Adelphi for 2 years where he also received his Master’s Degree. Last year he was the Head JV Coach at St. John the Baptist High School. This year he will be the Head JV Coach at Floral Park High School.
Erin Tully: Girls Elementary School Director
Coach Erin Tully started her basketball career at Sacred Heart Academy. She was a 2-year varsity starter and captain both years while earning the Coaches Award. She then played college basketball at CW Post where her team made it to the NCAA Sweet 16 tournament. It was the most successful season that the school had in decades. Erin is excited to join the Level Up family and have her passion for basketball live on through her players.
Bobby Barry: Director of Brand Partnerships & Brand Relations
Coach Bobby Barry started his playing career in upstate NY at Duanesburg High School where he brought his team to the state semi-finals and was named the MVP of his team and Western Athletic Conference All-Star. He went on to play 4 years of college basketball. His first 2 at HVCC where they were the #1 ranked Jr. College in the country. Bobby earned the honor of being the Captain of the team and winning the Coaches Award in his sophomore year. He continued his career at Alfred University where he became the captain of that team too. In addition, Coach Barry also played in the in Empire State Games his Sophomore and Junior year of college which showcased him as one of the top players in NYS during that time. Bobby has been involved in youth development for years now having experience working with the Varsity Basketball team at Don Bosco Prep in New Jersey as well as coaching CYO Basketball on Long Island.
Bobby brings over 15 years of experience at LinkedIn, including 8 years as the senior revenue leader across North America, where he has partnered with leading organizations to drive strategic growth and build high-impact relationships. He will continue coaching Level Up’s national teams, maintaining a direct connection to the athletes and culture that power the program.