During his time functioning in these prior roles, Mr. McDougall has had major landmark achievements working behind the scenes while being a Pioneer with the establishment of the Protocol and International Relations Unit in Tobago House of Assembly, the restructuring of the Tobago Festivals Commission Limited, the creation and incorporation of the Tobago Performing Arts Company, the establishment of the Tobago Tourism Agency Limited and being one of the first Managers appointed through the Ministry of Public Administration to lead the Government e-services in Tobago. It was through his efforts that the Annual Tobago Economic and Business Outlook Conference was realized. Correspondingly, Mr. McDougall was instrumental as a part of a dynamic team that assisted the Tobago Hospitality and Tourism Institute (THTI) in achieving Institutional Accreditation status.

Apart from his full-time engagement, Mr. McDougall with effective time management skills has helped organizations such as the Youth Training and Employment Partnership Programme (YTEPP) in developing and expanding their Small Business Management Training Programme. He has lectured at the undergraduate level for over 20 years with the Cipriani College of Labour and Cooperative Studies (CCLCS), College of Science and Applied Arts of Trinidad of Trinidad and Tobago (COSTAATT), the Tobago Hospitality and Tourism Institute (THTI) and School, School for Business Etiquette and Protocol Specialists in several academic disciplines. Additionally, Mr. McDougall is also a Certified Workshop Leader with Uplifting Service and a longstanding Trainer with the Elections and Boundaries Commission of Trinidad and Tobago.

Mr. McDougall was recognized by the Tobago House of Assembly (THA) for his contribution towards Sport Development when he was adjudged the Sport Administrator of the Year for two (2) consecutive years whilst as the Chairman, Tobago Basketball Zonal Commission. He also made vital contributions at the Corporate Governance level where he was also a former Vice Chairman of the Pigeon Point Heritage Park Board of Directors, Director and the Tobago Festivals Commissions Limited and a Member of the Tobago Sport Tourism Committee.

Mr. McDougall is a graduate and holder of both Post and Executive Masters of Business Administration from the Arthur Lok Jack Global School of Business (ALGSB), Post Graduate Certificate in Project and Risk Management from the Heriot-Watt University (HWU), Edinburgh, Scotland, Professional Certificate in Events Management from the George Washington University (GWU), USA, a Bachelor of Arts Degree in Business Studies from the University of Sunderland, an International Advanced Diploma in Administrative Management from the Institute of Administrative Management (IAM) and an Associate in Science Degree in Computer Science from the National Institute of Higher Education, Research, Science and Technology (NIHERST). Other Professional Certification include Tourism and Hospitality, Protocol and Diplomatic Relations and Capacity Building.