Skip to content
Dexter Wilson Jr.

Portfolio Vol. 01

DexterWilson Jr.

Communications Strategist

I build communications systems and data-driven AI solutions for public institutions and businesses. The goal is to reach the right people and move them to act efficiently.

Portrait of Dexter Wilson Jr.
Fig. 01 · Dexter Wilson Jr.SPECIMEN
  • Communications Strategy
  • Digital Marketing
  • Visual Storytelling
  • Public Sector Modernisation
  • Content Production
  • Stakeholder Engagement

What I believe

01

Communication should move people, not just reach them.

A message is only as strong as the system behind it. A good line on its own changes nothing. The strategy, the content and the way it reaches people have to be built together, or the campaign does nothing at all. I work in public-sector communications, digital marketing and visual storytelling, and I use all three on the same problem.

AI belongs in that system now. Not as a novelty, but as the part that reads the data, finds the pattern and shows you where to aim next. It has become a real component of how I get results, and I am as deliberate about where it should not be used as where it should.

How I got here

02

The stage came first.

My first audience was a stage, not a boardroom. I grew up performing in Tobago and learned early what it takes to hold a room, and how quickly you can lose one.

Film taught me the other half. Behind a camera I learned how a message is really built, piece by piece, and how much of it is settled before anything is recorded. Eight years on, the work has run through entertainment, retail, international marketing and public administration. Different rooms, same problem.

Today I work in strategic communications. I help public institutions modernise how they speak to the people they serve, and I help businesses earn attention they can keep.

Field plates
Dexter Wilson Jr. seated in a light-coloured suit
FIG. 02Portrait
Dexter Wilson Jr. seated on a low step
FIG. 03Portrait

8+

Years in media, marketing and public communications

3

Transformation programmes led

10+

Certifications in communications and marketing

What I do

03

Five disciplines that have to work together.

A message rarely fails because the line was weak. It fails because the strategy, the content and the audience were planned apart from each other. I work across all five so they stay together.

01

Communications Strategy & Governance

I write the communications strategy, the digital governance policy and the change management framework an institution needs to make a change stick.

02

Digital Marketing, Data & AI

Multi-channel campaigns, media buying and sales funnels, plus the data and AI tooling that reads what happened and shows where to aim next, in the public sector and in private business.

03

Content Production & Visual Storytelling

Onsite capture, editing, post-production workflow and drone camera work. Everything I shoot is built for distribution, not for the shelf.

04

Stakeholder Engagement & Brand Alignment

Stakeholder engagement, digital support workshops and brand alignment across divisions.

05

Public Speaking & Training

Keynotes, workshops and multi-week courses delivered to teams, executives and public-sector divisions, built from programmes I have already designed and run myself.

What I take on

04

The problems I take on.

Four kinds of problem, from a decade of practice in government, retail, media and international marketing. The client changes each time. The method holds.

  1. 01

    Transformation Communications

    Government & institutional

    Large-scale change inside organisations where the audience is internal, sceptical and hard to reach. I build the strategy, the message architecture and the alignment across divisions that carries a programme from announcement to adoption.

    • Strategy
    • Change communications
    • Adoption
  2. 02

    Digital Governance & Policy

    Public sector & regulated environments

    The governance, engagement and change-management frameworks that let digital services scale responsibly. I write them to be adopted, not published.

    • Policy authoring
    • Governance
    • Frameworks
  3. 03

    Brand & Campaign Systems

    Group, retail & media

    The marketing engine behind a growing group of companies: brand, campaign planning, media buying and the measurement that shows what worked.

    • Brand
    • Campaigns
    • Media buying
  4. 04

    Content Production at Scale

    Broadcast, digital & social

    Production from end to end: capture, edit, post and distribution, with a workflow that holds up against a real deadline. For organisations that need steady output, not one film.

    • Production
    • Workflow
    • Distribution

Where I've worked

05

What I learned doing the work.

Seven roles, condensed into the five things that matter most. Hover or focus a panel for the detail.

01

Communications lead for the THA Online Strategy.

I lead communications for the Tobago House of Assembly's online strategy.

Jun 2026 – Present

Communications Strategist, Office of Public Administration, Modernization and Digital Transformation

  • Designed and executed the Assembly-wide communications strategy for the digital identity initiative, the employee portal and the transformation roadmap.
  • Authored digital governance policies, stakeholder engagement frameworks and change management strategies.
  • Ran multi-channel campaigns, digital support workshops and brand alignment across divisions.
02

I learned the craft first, on the production floor.

Years delivering broadcast-standard content to a hard deadline.

Sep 2024 – Jun 2026

Technical Production Officer II / Video Editor I, Information Division, Office of the Chief Secretary

  • Special event video editing and end-to-end workflow management.
  • Onsite video capture and post-production.
  • Project planning, execution and reporting.
03

I have run a business, not a brand.

General manager across wholesale and media, with marketing on top of it.

Oct 2021 – 2024

General Manager & Creative Consultant, Windies Wholesalers & WindiesMedia

  • Managed daily operations across the wholesale and retail divisions.
  • Developed and led creative marketing, digital media and physical activation.
  • Oversaw team efficiency and stakeholder satisfaction.
04

I produced original series for Tobago.

Produced by me and funded by the Tobago Festivals Commission.

Jun 2019 – Jul 2021

Content Producer, Bliss Entertainment Ltd.

  • Produced digital series in partnership with the Tobago Festivals Commission, who funded the work.
  • Launched virtual campaigns, including a Black Lives Matter initiative.
05

I learned marketing where the market is ruthless.

International campaigns, media buying, and then teaching it.

2018 – 2019

Digital Marketing Strategist (Thailand) & Digital Marketing Lecturer · Marketing Assistant, G.R.A.D.S.

  • Managed and implemented digital advertising campaigns, media buying and sales funnels in the Thai market.
  • Designed and taught the digital marketing syllabus at the School of Practical Accounting.
  • Scripted and produced multi-channel content across TV, radio and social media.

Training & qualifications

06

Academic and professional grounding.

Degree

B.Sc. Accounting (Hons), Minor in Management Studies

The University of the West Indies, St. Augustine

Financial analysis, communications, business strategy and market dynamics.

12 certifications shown

Core credential2025

Microsoft Public Relations and Communications Associate Professional Certificate

Microsoft · Coursera

Media relations, stakeholder management and crisis communications, taught to a professional standard. This is the formal base under everything else I do.

Core credential2020

Project Management for Development Professionals

Inter-American Development Bank

Development-sector project delivery: planning, execution and evaluation. This is what turns a communications strategy into a programme that lands.

  • Data, AI & Governance2026

    AI Strategy and Governance

    University of Pennsylvania · Coursera

  • Data, AI & Governance2026

    Data Privacy, Security, Governance, Risk and Compliance

    SkillUp · Coursera

  • Production & Craft2024

    The Art of Visual Storytelling Specialization

    University of Colorado Boulder

  • Marketing & Growth2024

    Omnichannel Retail Strategy Specialization

    University of Pennsylvania

  • Marketing & Growth2021–2024

    Marketing Mix Implementation Specialization

    IE Business School

  • Marketing & Growth2024

    Marketing with TikTok

    Aptly

  • Production & Craft2024

    Understanding the Essentials of Video Production

    Certificate

  • Marketing & Growth2020

    Fundamentals of Digital Marketing

    Google

  • Marketing & Growth2020

    Facebook Certified Digital Marketing Associate

    Meta

  • Leadership2018

    Faith in the Commonwealth: Youth Training of Trainers

    The Commonwealth

Speaking & Training

07

Bring me in to teach it.

Keynotes, workshops and multi-week courses in digital communications, content, blockchain and AI literacy, for teams, executives and public institutions.

See speaking & training

The archive

Photograph from Dexter Wilson Jr.'s archive, plate 19 of 23.
FIG. 19
Photograph from Dexter Wilson Jr.'s archive, plate 20 of 23.
FIG. 20

Contact

08

Let's build something people remember.

Working on a campaign, a communications strategy, or a story that needs telling? Tell me where you are headed and we will work out how to get there.

Email me · meet@dexterwilsonjr.com
Based in
Tobago, Trinidad & Tobago

The archive

09

Frames from the way here.

Photographs from across the years. A visual record of the work and the years that shaped it.

17 of 20 plates · the other 3 appear earlier on this page

Photograph from Dexter Wilson Jr.'s archive, plate 5 of 23.
FIG. 05
Photograph from Dexter Wilson Jr.'s archive, plate 6 of 23.
FIG. 06
Photograph from Dexter Wilson Jr.'s archive, plate 7 of 23.
FIG. 07
Photograph from Dexter Wilson Jr.'s archive, plate 8 of 23.
FIG. 08
Photograph from Dexter Wilson Jr.'s archive, plate 9 of 23.
FIG. 09
Photograph from Dexter Wilson Jr.'s archive, plate 10 of 23.
FIG. 10
Photograph from Dexter Wilson Jr.'s archive, plate 11 of 23.
FIG. 11
Photograph from Dexter Wilson Jr.'s archive, plate 12 of 23.
FIG. 12
Photograph from Dexter Wilson Jr.'s archive, plate 13 of 23.
FIG. 13
Photograph from Dexter Wilson Jr.'s archive, plate 14 of 23.
FIG. 14
Photograph from Dexter Wilson Jr.'s archive, plate 15 of 23.
FIG. 15
Photograph from Dexter Wilson Jr.'s archive, plate 16 of 23.
FIG. 16
Photograph from Dexter Wilson Jr.'s archive, plate 17 of 23.
FIG. 17
Photograph from Dexter Wilson Jr.'s archive, plate 18 of 23.
FIG. 18
Photograph from Dexter Wilson Jr.'s archive, plate 21 of 23.
FIG. 21
Photograph from Dexter Wilson Jr.'s archive, plate 22 of 23.
FIG. 22
Photograph from Dexter Wilson Jr.'s archive, plate 23 of 23.
FIG. 23