Board of directors

As President and Chairman of Portland Holdings Inc., Michael oversees a broad private portfolio spanning financial services, insurance, tourism, agriculture, consumer goods and services, real estate development, energy and targeted radionuclide therapy. His entrepreneurial spirit is guided by his philosophy of merging profitability with social responsibility.

Michael’s many contributions to business and philanthropy have been recognised with the bestowal of the Order of Jamaica and the Order of Ontario, reflecting his impact in both domains. Michael’s impact is also recognised with honorary Doctor of Laws degrees from distinguished universities including the University of the West Indies, Northern Caribbean University, McMaster University, the University of Toronto, Wilfrid Laurier University and York University.

In addition to his corporate leadership, Michael is a trusted voice sitting on several boards across Canada and the Caribbean, such as National Commercial Bank Jamaica Limited, Guardian Holdings Limited and Portland Investment Counsel Inc. as well as in Europe, and the United States, where he continues to influence with his visionary approach.

Gary Brown, a seasoned director in the financial services industry, brings over four decades of experience to his role. He retired in 2018 after a distinguished 42-year career, culminating in his position as Chief Executive Officer and Director of FirstCaribbean International Bank Limited, a publicly-traded bank headquartered in Barbados and majority-owned by CIBC. In addition to his distinguished service within the financial sector, since 2006 he has served Mercy Ships International, where he is currently Chairman of the Board of Directors, and previously Chaired the Audit, Finance and Compliance Committees.

For nine years during his tenure at CIBC, Gary was President and CEO of CIBC World Markets Corp., the bank’s U.S. broker-dealer, overseeing their U.S. business and governance functions. He also held key leadership roles within the parent bank CIBC, contributing to its strategic direction as a member of the Operating Committee.

Prior to his time at CIBC, Gary served as Director and President of K2 Digital, Inc., an Internet professional services company. His extensive experience also includes nearly two decades with UBS AG, where he held various senior positions, including New York Branch Manager, Head of Structured Finance and Chief Credit Officer for the Americas. He began his career with The Chase Manhattan Bank in 1976.

Throughout his career, Gary has been actively involved in industry organisations and served in leadership roles, including President of the Risk Management Association – New York Chapter and Trustee of the Institute of International Bankers. He currently chairs the Audit Committee at Oral Roberts University and serves on the Board of Trustees.

Gary holds a Bachelor of Science in Business Administration from Oral Roberts University and has completed executive programmes at the Salzburg Institute and Harvard Business School. He is passionate about leveraging his leadership abilities and expertise to drive positive change and contribute to the success of organisations with whom he is affiliated.

John R. Bailey is an accomplished entrepreneur, investor and executive, with over 37 years of comprehensive experience in business development, strategic planning, and leadership. His expertise spans various industries, from Real Estate Development, Tourism and Finance, to Manufacturing, Hospitality and Food and Beverage.

John owns and operates Virginia Dare Jamaica Limited and Culligan Jamaica (W.E.T. Jamaica Limited). Through these – and a range of other ventures – he has demonstrated an acuity for systematically driving sustainable growth outcomes and transforming organisations. John holds a BA in Business Administration from the University of South Florida, along with advanced training in leadership and marketing strategies.

Leveraging his experience and expertise, John also serves on several boards, including One Great Studio, Dolphin Cove Jamaica, One on One Educational Services Limited, R.A. Williams Limited, Sagicor Real Estate X Fund and the White River Marine Association, among others.

Sandra is the founder and managing director of BizTactics Limited; co-founder and managing director of RevUP Caribbean Limited; and co-founder of Jamaica’s first angel investor network – First AngelsJA. An astute businesswoman, she holds a Bachelor of Science Degree in Marine Biology, a Master’s degree in Business Administration, and was Jamaica’s Eisenhower Fellow in 2000.

In January 2020, she was appointed senator, representing Jamaica at the World Business Angels Investment Forum (WBAF) and in 2022, vice president for the Caribbean at the Latin America and Caribbean Business Angels Network (LACBAN). Sandra also serves as a director of National Commercial Bank Jamaica Limited and chairs the NCBFG Group Risk Committee. She is a director on the boards of Multicare Youth Foundation Limited, DRT Communications Limited, SiFi Studios Jamaica Limited, Stanley Motta Limited and the Students Loan Bureau. She also serves on the Global Network Council of Eisenhower Fellowships and the Technical Committee of Scale LLC, a new VC Fund serving the Caribbean.

Sandra chairs the Board of Directors of the National Crime Prevention Fund (Crime Stop) and is Chairperson and trustee of the SMART Retirement Fund, as well as a trustee for the NCB Pension Funds. She is the Honorary Consul for the Republic of Suriname in Jamaica.

Roger Blissett is an international investment and commercial banking executive with more than 30 years of experience in the US banking industry. With expertise in legal, government, and regulatory affairs, he has set strategy and evaluated risk for leading global financial institutions, including Mitsubishi Union Financial Group (MUFG) and Royal Bank of Canada in New York, amidst major regulatory and operational transition.

In 2024, Roger decided to channel his extensive industry experience in US banking and securities regulations and government affairs into providing management consulting services through his firm, EVS Advisors, to early stage and legacy financial services organisations.
He has served on several boards of industry, civic, and philanthropic entities and currently serves as Chair of the governance committee for ExpandED Schools.

Roger holds a Bachelor of Arts in Economics and African Studies from Wesleyan University and a Juris Doctor degree from New York University School of Law. He is an alumni of the David Rockefeller Fellows programme sponsored by the Partnership for New York City.

Allison Philbert is an accomplished leader with over 20 years of experience in telecommunications and technology. She has held key executive roles at Digicel Jamaica and Verizon Communications, where she managed multi-billion-dollar operations, drove market expansion, and implemented strategies to improve customer experience and stakeholder outcomes.

Allison is the Founder and CEO of Allison Cole Philbert LLC, a boutique advisory and executive coaching firm focused on innovation, growth, and customer success. She currently serves as a director of Wigton Energy Limited and as Chair of QuickCart 2015 Limited. She has also served on the boards of the Jamaica Civil Aviation Authority and Aeronautical Telecommunications (Aerotel) Limited.

David W. Roberts is a visionary leader with over thirty years’ experience driving technological innovation across regulated industries, government systems, and financial services.

David has led high-impact projects such as large-scale artificial intelligence (AI) programmes, hybrid cloud deployments, and Enterprise Resource Planning transformations. As founder and CEO of Transform Affinity based in Georgia, USA, he leads digital transformation initiatives, delivering secure software solutions with lean-agile and cloud-first strategies for rapid, impactful results. As Chief Technology Officer at Mscale LLC, he provides strategic and governance expertise, contributing to initiatives like the Caribbean Venture Capital Fund, supporting early-stage firms in Jamaica and the Caribbean. Throughout his ten-year tenure at Booz Allen Hamilton, a leader in federal AI solutions, he drove innovation by delivering cutting-edge technologies in highly regulated environments.

Beyond his career, David is committed to community leadership. He chaired the Interservice/Industry Training, Simulation and Education Conference (I/ITSEC) Policy, Standards, Management, and Acquisition Subcommittee and serves on advisory boards for the Decide Dekalb Development Authority and Georgia Piedmont Technical College, focusing on advancing technology and nurturing the next generation of leaders.

David holds a Bachelor of Science degree in Operations Research & Industrial Engineering from Cornell University and a Master of Science degree in Computer Science from Johns Hopkins University. He earned certifications as Project Management Professional (PMP), Certified Information Security Manager (CISM), and Amazon Web Services Certified Solutions Architect. Recognised as a 2022 Black Engineer of the Year Modern Day Technology Leader, David continues to drive excellence in technology and governance.

Robert has over 35 years’ experience as both an investor and as a business executive across multiple industries and geographies. He entered the banking industry in 1998, leading the launch of an electronic bank by one of Canada’s leading banks. He has been involved with the NCB group of companies in a variety of capacities since 2002. In addition to his Chartered Professional Accountant (CPA, CA) designation, Robert holds a Bachelor of Commerce Degree with High Distinction from the University of Toronto. As an investor, Robert is a founding partner of Portland Private Equity, a leading private equity investor in the Caribbean and Latin America, and a portfolio manager at Portland Investment Counsel Inc. (Canada).

Currently, Robert serves NCBFG as an executive director in his role of Group CEO. He also serves as a director for a number of NCBFG’s subsidiaries including as Chairperson of Guardian Holdings Limited and NCB Jamaica Limited.