Christopher Cataldo
Chair (CLI Class of 2022)

Chris was born in Boston and raised on the South Shore of Massachusetts. He received his Bachelor of Science cum laude from Suffolk University. Upon entering the retail banking sector prior to graduation, Chris held the positions of Teller, Sales and Service Specialist, Personal Banker, and ultimately Relationship Manager with Bank of America. During his work as a banker, Chris became an active political candidate in two races for Selectman of his hometown of Norwell culminating in a 2016 run for the United States House of Representatives for the Massachusetts Ninth Congressional District. Returning to banking as a Branch Manager and Assistant Vice President, Chris continued his decade-long career in financial services. He went on to manage the Duxbury branch of Santander and the downtown Boston branch of Randolph Savings Bank. Upon marrying his wife Leigh, a Cape Cod native, he became a wash-ashore moving to Sagamore Beach and welcoming his two young daughters Charlotte and Eleanor.

Chris is a member of the Board of Directors of Cape Cod Media and the MassHire Cape and Islands Workforce Board. A past employee of Cape & Coast bank, he serves as a Vice President of Rockland Trust, managing the Duxbury Branch.

Kara O’Donnell-Galvin
Vice Chair (CLI Class of 2019)

Kara’s extensive experience in workforce development, youth
programming and economic advancement make her a vital asset to the organization. In addition to her role as executive director of the MassHire Cape & Islands Workforce Board, she
also serves on several boards and councils across the region and is dedicated to mentoring
emerging leaders through Leadership Cape Cod and EforAll Cape Cod.

Bill O’Neill
Treasurer (CLI Class of 2012)

A journalist, editor, and nonprofit fundraiser, Bill has served on the boards of the Association to Preserve Cape Cod and the Cape & Islands Self-Reliance, among others. His leadership experience and long-standing dedication to environmental and social justice causes enrich the organization’s strategic direction.

Haley Cote
Clerk (CLI Class of 2022)

Serving since 2024 as Chief of Staff for the Cape Cod Chamber of Commerce. Haley, a Cape Cod native, received her bachelor’s degree in journalism from Suffolk University in 2014, going on to work as a journalist and editor for the Cape Cod Times and Cape Cod Life Publications. She also previously served as a Community Manager for CapeSpace, a coworking company that operates shared workspaces in Hyannis and Mashpee. Haley has a deep appreciation and understanding of the Cape community and enjoys serving the individuals and businesses that make Cape Cod so special. She enjoys spending her free time exploring the Cape with her friends and family and going to concerts whenever she can.

Jake Stapledon
Chair Emeritus (CLI Class of 2018)

As the Community Engagement and Education Program Manager for Children’s Cove, the Cape & Islands Child Advocacy Center, Jacob advances the organization’s mission through comprehensive outreach and awareness initiatives across Cape Cod, Martha’s Vineyard, and Nantucket. He specializes in providing professional training for child-serving sectors on recognizing and reporting crimes against children—specifically sexual abuse and trafficking—while also addressing the management of secondary traumatic stress. Beyond his direct educational programming and multidisciplinary partnership management, Jacob holds several key leadership roles, including serving as co-chair of the Massachusetts Children’s Alliance statewide education and training forum, Chair for Leadership Cape Cod Inc., and Clerk for the Friends of Children’s Cove Board of Trustees. A graduate of the Community Leadership Institute of Cape Cod, his dedication to child safety has been recognized with the Massachusetts Children’s Trust Faces of Prevention Award and the Cape & Plymouth Business 40 Under 40 Award.

Margot Cahoon
Director (CLI Class of 2016)

Margot brings communications and marketing expertise to her role. As PR Director of Two Crows Creative, Margot helps nonprofits and mission-driven organizations thrive through strategic messaging, branding, and public engagement. She also supports community programs at the Cape & Islands District Attorney’s Office, and serves as communications director for Decatur House Assisted Living.

Rob Cushing
Director (CLI Class of 2019)

Founder and president of Port & Starward Digital Marketing, Rob was born and raised in Hyannis, spending his high school years in Iowa. Upon graduation, he entered into the Navy for 6 years, serving during the Persian Gulf War and at duty stations in Florida, Italy, and Virginia. Post-Navy, at Cape Cod Community College he served as Vice President of the Student Senate and as part of the WKKL Radio Club. He graduated with an associate’s degree in Information Systems, and then to the University of Massachusetts Dartmouth for his bachelor’s degree in 2000.

Rob previously worked for over 15 years in the field of technology project management with various Fortune 500 companies. He started Port & Starward Digital Marketing in 2014, a national agency that specializes in digital marketing including reputation management, search engine optimization (SEO), social media management, and business development/web design. Rob is also a musician and has toured throughout the country with music having been featured on MTV. He spends his free time with his son Leo or can be found working on his music, enjoying the Cape, or exploring genealogy.

Susan Cyr
Director (CLI Class of 2025)

Susan retired in 2024 to live full-time in Harwich, Massachusetts. She has strong ties to the Cape, as she and her husband Craig have owned their home here for over 20 years. Susan’s CLI experience introduced her to multiple ways to craft her Act 2, and she is excited to add Leadership Cape Cod as part of the next step in her journey.

Susan’s career included multiple leadership positions across several industries. Her most recent position was Vice President of Global Service Operations at UKG (Ultimate Kronos Group). She spent the first part of her career in Finance and Operations, working for both May Department Stores and Gap Inc., Susan’s focus in all her roles was building strong teams through people development to deliver successful results.

Susan has a B.S. in Finance from the University of Connecticut. Her transition to life on the Cape full-time has enabled her to continue her love of all things outdoors. Susan is active in local conservation efforts in Harwich through her leadership position in the Harwich Ponds Coalition and her recent addition to the Conservation Commission for the Town of Harwich. Susan also volunteers with the Garden Club of Harwich and the Family Pantry of Cape Cod.

Adam Gracia
Director (CLI Class of 2025)

Adam is the executive director of CARE for the Cape & Islands and has worked nationally and locally in the nonprofit industry with a focus on raising support for community resources, affordable housing, and disease research for over 20 years. Raised on Cape Cod, Adam is a graduate of Sandwich High School. He earned his B.A. from Westfield State and his M.A. from Webster University. Adam is also a veteran with service in the Army National Guard and the Ukrainian International Legion and lives in Chatham with his family.

Michael McGee
Director (CLI Class of 2026)

Michael McGee is a United States Marine Corps veteran who served in Afghanistan during Operation Enduring Freedom. His time in uniform shaped a steady, practical approach to leadership, one grounded in accountability, clear communication, and a deep respect for the people he serves.

For more than a decade, Michael has called Cape Cod home. As Program Manager of Case Management Services at the Cape & Islands Veterans Outreach Center, he leads a team dedicated to helping veterans secure stable housing and rebuild independence. His work centers on thoughtful case planning, strong collaboration across agencies, and a consistent focus on long-term outcomes rather than short-term fixes. Inter-agency communication and coordinated problem-solving have been at the heart of much of his professional experience.

Michael brings the same quiet determination to his broader community roles. He also serves on the Board of 22Mohawks, Town of Dennis Planning Board, and as the Town of Dennis Representative to the Cape Cod Commission. He founded the 22K9 Motorcycle Ride to support the Pups for Vets program and remains actively involved in local civic life.

Whether working with a veteran facing a housing crisis or collaborating with community partners, Michael is known for a calm, professional presence and a focus on getting the work done well. In his free time, he values the quiet company of his dogs and the ongoing opportunity to strengthen the community he calls home.

Keniqua “Kenni” Smith
Director (CLI Class of 2024)

David Troutman
Director (CLI Class of 2015)

David has worked in the restaurant industry for over 50 years, most notably since 1987 as co-owner of Scargo Cafe in Dennis.

A 1976 graduate of Barnstable High School, he received his bachelor’s degree from Suffolk University in 2006 and is a graduate of the class of 2015 Community Leadership Institute.

He is a founding member and immediate past Chair of Calmer Choice and as such was the United Way recipient of the 2015 Ron Reed Award for dedication to a board. David is also an active member of the YMCA “Achievers” steering committee, an active Trustee on The Cape Cod Chamber of Commerce board, a member of the PAWs advisory board as well as recently becoming a member of the board of WE CAN.

With volunteerism as a primary passion, David has been featured in recent years as a dancer for Cape Wellness Collaborative’s “Dancing With The Docs”, a mentor for Big Brothers Big Sisters, as well as a presenter for several of SCORE‘s educational seminars. David lives in West Barnstable with his beautiful wife Pam and his lovely daughter Kate.