Skip to Content
In Search of a Spark

In Search of a Spark

How a Digital Marketing Agency was built from the rubble of a Category 5 Hurricane to market the largest OECS event of 2021!

Tuesday, July 13, 2021 — The Valley, Anguilla — It has been almost 4 years since Gino Webster and Tahirah Banks sat in the darkness of their hurricane-ravaged apartment on the tiny island of Anguilla. They were in search of a spark.

With their physical businesses devastated by the category 5 hurricane Irma, the young couple knew they needed something exciting to reignite their professional lives.

“We were in our mid to late 20s and the prospect of starting over from scratch was daunting, but we knew we had ideas for our region that, if we gave it our full attention, would be worth pursuing," the duo reflected on the experience.

A week later they rebranded as Thoughtful Digital Agency, a full-service Digital Marketing Agency, that today is based in Anguilla and Houston, Texas.

“We printed 15 shirts, with the first iteration of the logo, in St. Kitts because there was no power in Anguilla”, Gino (Co-Founder & CTO) reminisces. “We would charge our devices at an office in town and work from our balcony at home, with the cows and goats and construction as our background music.”

It is impossible to debate that today, the agency is one of the fastest-growing and most innovative brands in the Caribbean. With a young team of ten (10) and an impressive roster of clients up and down the archipelago and throughout the United States, people are talking more and more about Thoughtful. 

Most recently Thoughtful had a big win, signing an agreement with the Organisation of Eastern Caribbean States, as the agency of record for the OECS Sustainable Development Movement 2021.

“SDM is the annual flagship event of the OECS in its work to build a sustainable Caribbean. It is a natural fit for us to work with a team as passionate and innovative as Thoughtful,” Lisa Taylor-Stone, the OECS Head of Development Cooperation & Resource Mobilisation Unit remarked on the partnership.

The OECS SDM is the largest event of its type, creating a common space, where over 10,600+ Development Partners, the Private Sector entrepreneurs and investors, Academia, Caribbean Governments, Civil Society, and individuals gather virtually to exchange thoughts and agitate action around innovative sustainable growth and development of Small Island Development States (SIDS). 

The 2021 iteration of the SDM Summit is positioned to fast-track the fruition of the Eastern Caribbean Economic Union, through disruptions, solid innovations, and agility, thereby fostering exponential growth and inclusion for all. 

An award-winning ambassador of the 2020 OECS SDM, now selected as a global ambassador for 2021, Thoughtful co-founder, Tahirah Banks, welcomes the opportunity.

“Our agency’s starting point and growth over the years is an example of what the OECS and the Sustainable Development Movement advocate for, day in and day out. Our region and our people are faced with what may sometimes feel like impossible decisions when it comes to building and sustaining our livelihoods. Initiatives like SDM and the work of our other clients support our individual and collective growth towards long-term success.” 

Thoughtful has gone all-in on the move towards building a sustainable Caribbean. The company’s promise, “moving messages that matter”, is manifested in its clientele, community programs, and initiatives. 

Tahirah and Gino hold Entrepreneurship Workshop with 6th form students (2020)
Tahirah and Gino hold Entrepreneurship Workshop with 6th form students (2020)

In 2020, amidst the COVID-19 pandemic, the team launched its Sustainable Anguilla initiative in collaboration with the OECS. On the project, Thoughtful collaborates closely with stakeholders and industry partners to provide free programming that targets technology innovation, environmental protection, and the adoption of renewable energy to the people of Anguilla.

“Our region is overly susceptible to unexpected shocks and economic shutdowns that impact our ability to feed our families and live productive lives. Our work with Thoughtful extends beyond marketing. We have a big vision to see Anguilla as the digital capital of the Caribbean. Bigger than that though, we could never consider ourselves successful until our region is benefiting from the transformations and opportunities that come with technology innovation. It is an ongoing process and training is the answer— that is why we started Sustainable Anguilla and Thoughtful Labs," Tahirah reflected.
Gino Webster and Tahirah Banks, Co-Founders of Thoughtful Digital Agency
Gino Webster and Tahirah Banks, Co-Founders of Thoughtful Digital Agency

The co-founders, together with their young team, have doubled down on training, expanding their Thoughtful Labs brand to include programming for entrepreneurs, start-ups, business professionals, and island people of all ages, who are committed to improving their technology, business, and marketing literacy. Most recently, Banks has partnered with the University of the West Indies Open Campus to, using elements of the Thoughtful Labs curriculum, train entrepreneurs & small business leaders in the British Overseas Territories.

“On a personal level, building this relationship with the OECS continues to be an opportunity for me to live out my commitment to creating opportunities for people to live their dreams. When I look at our core team, our clients, and the people whose lives we positively impact every day with projects like SDM, I can say “yes, we’re doing it!”.”

Although it is approaching four years since Hurricane Irma devastated Anguilla, this September, Thoughtful can say it has found its spark. Today, as an internationally recognized digital marketing agency, the team at Thoughtful reflects what the Organisation of Eastern Caribbean States, through projects like SDM, hopes to develop; A Sustainable Caribbean built by Sustainable Caribbean People.

Commenting on the partnership, Dr. Didacus Jules, Director General of the OECS shared:

“We are proud to partner with the team at Thoughtful Digital Agency. Their work highlights the talent and potential of Caribbean people to deliver World-Class solutions that support our long-term regional development.”

Thoughtful is a Strategic Digital Marketing Agency. Notable clients include The Anguilla Tourist Board, Digicel Group, Decision Information Resources, The Eastern Caribbean Central Bank, The Global Coalition for St. Vincent, The Deutsche Gesellschaft für Internationale Zusammenarbeit (GIZ), The Anguilla Ministry of Health, The Anguilla Department of Education, The Red Cross, The Organisation of Eastern Caribbean States.


For more about SDM 2021 and the upcoming People Summit 



Learn more about Thoughtful when you visit

For press inquiries please email [email protected] 

​ ​

SDM Secretariat | OECS Commission
SDM Secretariat | OECS Commission Castries, Saint Lucia
OECS Communications Unit Organisation of Eastern Caribbean States
Business Economic Development International Relations Social Development
About The Organisation of Eastern Caribbean States

Back to

The Organisation of Eastern Caribbean States (OECS) is an International Organisation dedicated to economic harmonisation and integration, protection of human and legal rights, and the encouragement of good governance among independent and non-independent countries in the Eastern Caribbean. The OECS came into being on June 18th 1981, when seven Eastern Caribbean countries signed a treaty agreeing to cooperate with each other while promoting unity and solidarity among its Members. The Treaty became known as the Treaty of Basseterre, so named in honour of the capital city of St. Kitts and Nevis where it was signed. The OECS today, currently has eleven members, spread across the Eastern Caribbean comprising Antigua and Barbuda, Commonwealth of Dominica, Grenada, Montserrat, St. Kitts and Nevis, Saint Lucia, St Vincent and The Grenadines, British Virgin Islands, Anguilla, Martinique and Guadeloupe. 

The Organisation of Eastern Caribbean States
Morne Fortune
Saint Lucia