On 1 October 2026, the Cayman Islands Monetary Authority (CIMA) announced the appointment of Gloria Glidden as Chief Supervision Officer, Investments & Innovation, as part of its continuing organisational restructuring. The appointment establishes a dual Chief Supervision Officer structure, separating oversight of investments, securities, virtual asset service providers (VASPs), FinTech innovation and authorisations from traditional financial services supervision. Anna McLean will continue as Chief Supervision Officer, Traditional Financial Services, overseeing banking, fiduciary services, insurance and onsite inspections. CIMA also appointed Shakira Cox as Acting Head of Banking Supervision and Kieron Cacho as Acting Deputy Head. The changes, effective 1 October 2026, are intended to strengthen sector-specific oversight, accountability and supervisory effectiveness across the Cayman Islands financial services industry.1
CIMA Introduces Dual Chief Supervision Officer Structure
The Cayman Islands Monetary Authority has announced a significant change to its senior supervisory leadership through the appointment of a second Chief Supervision Officer (CSO). The restructuring introduces two distinct supervisory portfolios: Investments & Innovation and Traditional Financial Services. The new arrangement is intended to provide more specialised oversight of the different sectors regulated by CIMA. Previously, supervisory responsibility was concentrated under a single senior supervision function. Under the revised structure, leadership responsibilities are divided between Gloria Glidden and Anna McLean.
Gloria Glidden Appointed Chief Supervision Officer, Investments & Innovation
Gloria Glidden has been appointed Chief Supervision Officer, Investments & Innovation, effective 1 October 2026. Her responsibilities encompass four supervisory divisions:
- Investments Supervision Division.
- Securities Supervision Division.
- VASP & Fintech Innovation Division.
- Authorisations Division.
New Authorisations Division to Manage Licensing and Registration Applications
CIMA has also established a dedicated Authorisations Division. According to the announcement, the new division will manage all registration and licensing applications. The division will operate under the Chief Supervision Officer, Investments & Innovation. This is an important organisational development because licensing and registration are central functions of financial services regulation. The new structure provides a dedicated administrative division for processing regulatory authorisations. For applicants, including investment entities, financial services providers and VASPs, the restructuring may affect the internal supervisory arrangements through which applications are managed.
Anna McLean to Oversee Traditional Financial Services Supervision
Anna McLean will serve as Chief Supervision Officer, Traditional Financial Services. Her responsibilities will cover:
- Banking Supervision.
- Fiduciary Supervision.
- Insurance Supervision.
- Onsite Inspections.
Mrs McLean has served as CIMA's Chief Supervision Officer, formerly Deputy Managing Director – Supervision, since 2014. In that capacity, she previously oversaw all supervisory divisions. Under the revised structure, her responsibilities will be concentrated on traditional financial services sectors. CIMA states that this more targeted allocation of responsibilities is intended to support deeper sector-specific oversight and improved supervisory effectiveness.
Shakira Cox Appointed Acting Head of Banking Supervision
Shakira Cox has been appointed Acting Head of the Banking Supervision Division. Ms Cox brings more than a decade of specialised supervisory and audit experience. She has served as Deputy Head of Banking Supervision since 2017. Her responsibilities have included supporting the management and operation of the division across onsite and offsite supervisory activities.
Kieron Cacho Appointed Acting Deputy Head of Banking Supervision
CIMA has appointed Kieron Cacho as Acting Deputy Head of the Banking Supervision Division. Mr Cacho will support the division's leadership and management and assist in delivering its supervisory responsibilities. He previously served as Chief Analyst.
CIMA CEO Highlights Sector-Specific Supervisory Approach
CIMA Chief Executive Officer Cindy Scotland, OBE, described the restructuring as a deliberate move towards more specialised financial supervision. She stated:
"The introduction of specialised CSO roles allows us to sharpen our supervisory focus and ensure leadership is aligned with the distinct risks and characteristics of each financial services sector."
"These changes strengthen accountability, enhance organisational efficiency, and support further development and upward mobility for our staff."
CIMA has confirmed that further organisational updates will follow as the phased transition progresses.
Footnotes
- Cayman Islands Monetary Authority, CIMA Announces Second Chief Supervision Officer, news release, 1 October 2026.
- Ibid., concerning the appointment of Gloria Glidden as Chief Supervision Officer, Investments & Innovation, and her responsibility for the Investments Supervision, Securities Supervision, VASP & Fintech Innovation, and Authorisations Divisions.
- Ibid., concerning Anna McLean's appointment as Chief Supervision Officer, Traditional Financial Services, with responsibility for Banking Supervision, Fiduciary Supervision, Insurance Supervision and Onsite Inspections.
- Ibid., concerning the appointments of Shakira Cox as Acting Head and Kieron Cacho as Acting Deputy Head of the Banking Supervision Division.
- Ibid., describing organisational reforms initiated in October 2024, including changes to senior management titles, legal and enforcement functions, AML arrangements and divisional reporting lines.
- Ibid., statements of CIMA Chief Executive Officer Cindy Scotland, OBE, concerning specialised supervision, institutional accountability and organisational efficiency.
- Cayman Islands Monetary Authority, official website, www.cima.ky, for subsequent announcements, regulatory notices and supervisory guidance.
