Jake Stapledon
Chair (CLI Class of 2018)

Jacob works as the Community Engagement and Education Program Manager for Children’s Cove of the Cape & Islands Child Advocacy Center. Jacob supports the mission of Children’s Cove by providing outreach, education, and awareness to Cape Cod and the islands of Nantucket and Martha’s Vineyard about crimes against children. Jacob provides training to multidisciplinary professionals to effectively recognize and respond to child abuse, as well as prevention education for organizations, parents, and the at-large community. Jacob coordinates organizational communications, and community awareness campaigns, as well as establishes and maintains community and multidisciplinary team partnerships. Jacob has provided numerous regional and national presentations and workshops including at the National Children’s Alliance Leadership Conference.

Jacob also serves as co-chair of the Massachusetts Children’s Alliance statewide education and training forum, is a graduate of the Community Leadership Institute of 2018,  is a recipient of the Cape & Plymouth Business 40 Under 40 Award and the Faces of Prevention award from the Children’s Trust. He is a member of Cape Cod Young Professionals and is a partner to a wonderful woman, a father of incredible twins, and a craft beer enthusiast.

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.

Christopher Cataldo
Clerk (CLI Class of 2016)

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. Chris also serves as a Vice President of the Cooperative Bank of Cape Cod, managing the East Harwich Branch.

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.

Alicia Conlin
Director (CLI Class of 2025)

Alicia works as the executive director of WellStrong in Falmouth and was elected by her CLI classmates to serve as the 2025 representative for the Leadership Cape Cod board of directors. A strong advocate for inclusive, recovery-
friendly spaces, Alicia brings a deep commitment to community resilience. Her leadership at
WellStrong, a nonprofit supporting individuals in recovery through fitness, mindfulness, and
peer support, reflects her values of compassion, growth, and empowerment.

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 12-year-old son Leo or can be found working on his music, enjoying the Cape, or exploring genealogy.

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.