Building upon our rich history of success, the Community leadership Institute of Cape Cod and the Islands in 2019 made a strategic decision to broaden its offerings. To fulfill the mission of inspiring, developing, and connecting current and future leaders for the betterment of the community, CLI was enveloped under Leadership Cape Cod.

Leadership Cape Cod works to make more of an impact by offering more programs and services to more people, businesses, and community organizations.

Leadership Cape Cod goals are:

  • To provide the tools for leaders to thrive in their businesses and community.
  • To enhance leadership and civic engagement (community service) skills.
  • To cultivate connections and foster thoughtful conversations and collaborative skills.
  • To offer a learning community network of friends and colleagues.
  • To drive change and innovation while helping to shape the future of the Cape Cod region

Board Of Directors & Staff

Jacob 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.

Jeni Wheeler
Vice Chair (CLI Class of 2019)

Jeni is the co-founder of the Family Table Collaborative, a nonprofit organization dedicated to ending hunger and improving nutritional security on Cape Cod. She is also Owner/Chief Culinary Artist of Jeni’s Joy, a boutique prepared meals and catering company focusing on people with specific food preferences/needs such as Vegan, Keto, Gluten-free, etc. She was previously the Executive Chef and Program Director of Faith Family Kitchen, a ministry of the Cape Cod Council of Churches which feeds the homeless and food insecure.

Jeni has an MBA from Babson College, with a focus on social entrepreneurship, and has extensive background working in start-ups, nonprofits, and the political sector.

Courtney Butler, MPA, MCPPO
Secretary (CLI Class of 2020)

Courtney is a proud public servant and graduate of the Community Leadership Institute. She moved to Cape Cod in 2015, to intern at the Cape Cod National Seashore (CCNS) for the summer; 7 years later she made the Cape is her permanent home. While at the CCNS, Courtney served as the park’s Superintendent Assistant, and working with the many towns within the Seashore, Courtney discovered her passion for municipal government. In 2021, Courtney received her MPA from Roger Williams University. Courtney has previously worked for the Town of Wellfleet and Town of Dennis in a variety of roles. Courtney currently serves as the Legislative Aide to Representative Chris Flanagan. Courtney lives with her partner, a Yarmouth firefighter in South Yarmouth. She spends her free time at home, on a nature trail, or at one of her favorite brunch spots reading true crime novels.

Christopher Cataldo
Director (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. Chris also serves as a Vice President of the Cooperative Bank of Cape Cod managing the East Harwich Branch.

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.

Kara O’Donnell
Director (CLI Class of 2019)

Kara currently serves as the executive director of the Cape & Islands Workforce Board.

Mike Solitro
Director (CLI Class of 2019)

Mike graduated from Syracuse University and Suffolk University Law School and now serves in several capacities in the Cape Cod area as an attorney, an associate broker with Kinlin Grover, and as the founder of AccomplishedRE.

He lives in Sandwich with his amazing wife and children along with their energetic dog. They love the outdoors and everything Cape Cod offers. Mike is also a member of Cape Cod Young Professionals and EforAll Cape Cod Spring 2021 Accelerator.

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.