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Our Coaches

High-Level Coaches for High-Level Players

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Ross Olsson

Owner and Director

As the current Head Coach at the Hillside School, Ross has a passion for teaching and player development. Prior to joining the coaching ranks, Ross played professional hockey with the Worcester Railers and the Solar Bears, where he held leadership positions on both teams.  His professional journey also includes time with the AHL teams Bridgeport Islanders and Providence Bruins. 

Ross is an alumnus of Endicott College, where he majored in Sport Management and earned an MBA. During his college years, Ross achieved the distinction of being the all-time points leader at Endicott with 134 points and was a semi-finalist for the Joe Concannon Award in 2017-2018.

Ross's growth and development in hockey have been significantly influenced by his time with high-level coaches. He has worked with David Cunniff, known for his 15 years as an AHL/Skill Development coach, Jon Lousbury, a former skill coach for the Florida Panthers and Holy Cross before joining the Oates Hockey Group, and Mike Ellis, a skill development coach for the Tampa Bay Lightning.

Dan Gordon

Senior Advisor and Development Coach

As the current Head Coach of the Pingree School, Dan has established a reputation for excellence and dedication in hockey. Prior to this role, Dan served as an Assistant Coach at Endicott College for four seasons and has experience coaching at the semi-professional, junior, and youth level since 2009. Over his three seasons involved with junior hockey, Dan helped move 11 players to NCAA Division I programs and 24 players to the Division III ranks. 

Dan's passion for the sport is rooted in an impressive playing career. Playing at UMass Amherst and Southern Maine, he was a finalist for the prestigious Joe Concannon Award in the 2008-2009 season, recognized as one of the best players in New England. This accolade highlights his outstanding performance and leadership on the ice.

Dan has also played Professionally for two seasons, one in Europe and one in the U.S. He has been running hockey camps, clinics and private lessons since 2010 and is passionate about coaching and youth development in the sport of Hockey.

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Jordan Smotherman

Development Coach

With a distinguished career spanning over a thousand professional games, Jordan stands as a prominent figure in the world of hockey. Currently the General Manager for the Worcester Railers of the ECHL, Jordan brings a wealth of experience and expertise to the team.

Jordan's career is marked by an impressive list of achievements. He was drafted in the 2005 NHL Draft in the 4th round as the 116th overall pick by the Atlanta Thrashers. He celebrated a significant victory as a member of the team that clinched the Memorial Cup in the 2005-2006 CHL season and further demonstrated his skill by contributing to the Calder Cup triumph in the 2007-2008 AHL season. His success continued internationally, where he led the Belfast Giants as a player/coach in the 2019-2020 season and secured the EIHL Cup Champion title in the 2018-2019 season.


Prior to his current role with the Worcester Railers, Jordan dedicated his expertise to scouting, serving as the New England Scout for the Quebec Remparts from 2020 to 2022. His keen eye for talent and deep understanding of the game have been invaluable in shaping the careers of young players.

Tyler Bird

Development Coach

As a current player for the Orlando Solar Bears in the ECHL, Tyler brings a unique blend of skill, leadership, and experience to the ice. Selected in the 5th round (137th overall) by the Columbus Blue Jackets in the 2014 NHL Draft, Tyler has not only showcased his talent but also a deep commitment to the sport.

Tyler's journey through hockey is marked by significant milestones, including an impressive tenure at Brown University, where he majored in Business Entrepreneurship and played on the men's ice hockey team. Tyler served as an assistant captain in his senior year, underscoring his natural ability to lead both on and off the ice.

Prior to joining the Orlando Solar Bears, Tyler also spent time with the Syracuse Crunch and the San Jose Barracuda in the AHL.

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Drew Callin

Development Coach

Drew currently showcases his talents as a player for the Springfield Thunderbirds in the AHL. His journey in the sport is marked by a strong foundation in both skill and strategy, honed through dedicated play and academic achievement.

A graduate of Bentley University, Drew earned his degree in Business Finance, balancing his academic pursuits with a thriving hockey career. His time at Bentley was not just about academics; he made a significant mark in the rink as well. Drew was honored with the 2018-2019 ECAC Defensive Forward Award, an accolade that speaks to his exceptional abilities in both offense and defense, highlighting his versatility and tactical acumen on the ice.

Drew's transition to the Springfield Thunderbirds has been a testament to his continuous growth and adaptability as a player. His performance continues to reflect his deep understanding of the game, a byproduct of his education and on-ice experiences, making him a valuable player and an exciting talent to learn from.

Conor O’Brien

Development Coach

Conor currently defends the goal for the Fayetteville Marksmen in the SPHL. His journey through the ranks of collegiate and professional hockey is marked by outstanding achievements and a steadfast commitment to excellence.

After a distinguished career at Endicott College, where he was a two-time All-American (2019-2020 & 2021-2022), Conor transitioned into professional hockey with a stint in Adirondack with the Thunder (ECHL).


His time at Endicott was highlighted not only by impressive individual accolades but also by remarkable statistical achievements: a .934 save percentage, a .736 win percentage, and a 2.00 goals-against average. These figures underscore his exceptional skill and consistency as a goaltender. In the 2021-2022 season, Conor's prowess on the ice was further recognized when he was named the Joe Concannon Co-Winner, an honor awarded to the best college hockey player in New England. This achievement speaks to his skill, determination, and impact on the game. 

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