Chris Hamilton

I can help your Key West organization or business thrive.

The things I accomplished over the last two decades come from an ability to motivate people, conquer the administrative work and market services. While going to college I worked at a big, downtown D.C. hotel with an international staff and learned the value of courteous and professional customer service, how to treat everyone in all parts of the organization with respect and the value of a diversity of people and ages in a work force. It stayed with me. In Arlington I honed organizational skills via leadership and management training and later was sought out to help teach new managers and staff the same. I learned marketing and social media skills working with the most innovative companies in the industry for almost two decades with amazing results. I can harness these skills to help organizations and businesses in Key West meet their goals.

A Dozen Easy Principles for Organizational Success” is an article I was asked to write explaining my Commuter Services Bureau team’s unique and amazing success when benchmarked versus other organizations using the Denison Culture Survey.

I tended to think of government as slow, bureaucratic, and monopolistic. Although I learned learned that this remains the case in many places, there are people such as Chris Hamilton and his team in Arlington County, Virginia who have the ambition and the ability to make change happen quickly. Finding those people helped to create demand for more change elsewhere in the region, and ultimately nationally.

Gabe Klein on page 146 of his book, Start-Up City, where he discusses the creation of Capital Bikeshare – the U.S.A’s first major bikeshare system and Chris’ critical role in making it happen. Gabe is the former Director for Chicago’s and Washington, D.C.’s Transportation Departments and now runs his own consulting firm.


I’ve marketed buses, biking, walking, bikeshare, behavior change, cities, home tours, a museum and live theater. I’ve worked with and learned from some of the best ad people in the world. I’m an avid follower of marketing guru Seth Godin.

On the Ground Sales

Local relationships with the lodging, retail, restaurant, attractions and general business community are the only way to move the needle. I work with people that know the island and can deliver local, part-time and visitor markets.

Social Media

The best marketing is peer to peer. I’ve helped pioneer the use of social media like Facebook, Twitter and Instagram as an integrated part of selling and behavior change. I work with the top firms in the field and constantly learn from the best.

Organization and Development

Moving a team forward, all on the same page, is a favorite specialty of mine. Strategy and planning. Research and data. Budgeting and performance measurement. Developing revenue to meet the organization’s mission. I geek out on these things and can help guide you in a forward direction.

Development Director at Red Barn Theatre

April, 2019 – Present (Part-time)
Support Managing Director with grant writing, producing and analyzing performance data; developing frameworks to initiate new ways of doing business; responsible for advertising and social media. Accomplishments: record scores on existing grants and developing and securing new grant monies. Streamlining performance data. New digital ads and Facebook growth.

Other Recent Gigs

I volunteer one day a week as a docent at the KWAHS Lighthouse.

One Manatee – Assist non-profit Founder Quincy Perkins with organizational and marketing as a volunteer.

Instagram and Facebook social media sites for WeCycle Key West.

Friends of Car-Free Key West & Duval Street/Historic Downtown

February 29, 2019 – Present
I own and manage this blog and its Facebook page where we advocate for a bike, walk, transit friendly Key West.

Keys Last Stand, Board of Directors

April 2022 – Present
“Promote, preserve, and protect the quality of life in the city of Key West, the Florida Keys and their environs, with particular emphasis on the natural environment.”

Administrator at OIRF and Oldest House Museum

Sept. 2017 – Dec. 2018
Led 5-person non-profit, Museum and volunteers: annual Key West Home Tours™, event garden rentals and OIRF programs. Accomplishments: developed record sponsorship of Home Tours, increases in membership, donations, events revenue and new grant sources from the County and State. Web, Facebook, marketing savvy!

Graduated CFFK Non-Profit Leadership Academy, 8/20/2021 – 7th from left.
Bike Coordinator at City of Key West Government

January 2016 – September 2017
Planned and promoted safe use of bike, walk, transit via marketing, web, social media, community and business outreach. Accomplishments: Secured $25K Bike Florida grant, launched the successful Duval Loop bus and “Car-Free Key West” campaign and secured state money for both. Key West Bike/Ped Plan to 85%.

Westwinds HotelDec 2018 – April 2019
Shared my love of Key West at front desk.

Commuter Services Bureau Chief/Customer Service Guru, Arlington County, VA DOT

January 1993 – June 2015

Starting with a few staff and a couple hundred thousand dollar budget, over the years built and led a 60+ person customer service unit promoting public transportation to the community, businesses and visitors that had a budget approaching $13 million annually. The unit was cited as the most innovative and award-winning team of its kind in North America. The Bureau included a call/fulfillment center, five retail stores, a B2B sales force, community outreach teams, a marketing unit, web and social media support and a research team providing a loop for customer feedback and continuous improvement. Started first major bikeshare in U.S. – “Capital Bikeshare.” Result: Decades of population/employment growth and no additional cars., WalkArlingtonBikeArlingtonArlington Transportation PartnersThe Commuter StoreCar-Free Diet, Capital Bikeshare, CommuterDirect.comTDM for Site Plan DevelopmentResearch, and Mobility Lab.

College and Continuing Education

Bachelor of Arts in Urban Studies in City Management and Urban Planning
University of Maryland, College Park, MD

Over the years I spent much time in volunteering at work, such as serving on the National Board of Directors of the Association for Commuter Transportation (ACT) and in the local Chesapeake Chapter. I was often sought after as a speaker at conferences. I served on my civic association board for almost a decade and served as President of the Warwick Village Citizens Association for 4 years. I was selected to serve on numerous City of Alexandria planning, development and traffic committees as well as the inaugural class of Leadership Alexandria in 2004. I was asked to participate in multiple leadership courses for Arlington County and assisted in on-boarding new managers and staff.

Engaging Local Government Leaders (ELGL) named me to its 2017 Traeger Award winners for Top 100 Influencers in Local Government. I came in at #42. As a result I got to do this cool podcast with them.

chris hamilton 170 at
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