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Chief Program Officer (CPO) – Insurance & Investments

An AI-powered 'Future of Work SuperApp' that connects Caribbean talent with global employment opportunities while providing skills-based training and certification.

TheHiveCareers51-200 employeesBarbados only

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About the job

Chief Program Officer (CPO) – Insurance & Investments

1. Role Summary

Top owner of the big programs and company-wide initiatives, many made up of several projects, that run across the insurance and investment businesses.

Makes sure major programs fit the strategy, have the people and money they need, are well governed, and land on time and on budget. Sets program standards, brings cross-functional teams together, manages linked projects, and makes sure strategic work produces measurable results.

Partners with the CEO, Board, and leadership team to turn company priorities into joined-up programs that support growth, operational excellence, digital change, compliance, and organizational development.

2. Key Responsibilities

Strategic Program Management

  • Create and roll out a programs management strategy for the whole organization.
  • Define, structure, rank, and oversee programs that serve corporate goals.
  • Turn strategy into programs with clear targets, milestones, outputs, and results.
  • Manage how projects, units, and strategic efforts depend on one another.
  • Track programs results and keep them in line with priorities.

Insurance & Investment Program Delivery

  • Head programs across life, general, reinsurance, investment, wealth, and other financial services.
  • Oversee insurance product development, modernized underwriting, claims transformation, policy administration, and distribution growth.
  • Where relevant, coordinate investment programs such as portfolio systems, operations, client reporting, and service.
  • Manage regulatory change, new business models, market expansion, and restructuring.
  • Make sure program outputs meet business needs and industry rules.

Program Governance & Management Office

  • Decide how programs are governed, run, and reported.
  • Produce charters, business cases, plans, risk registers, and dashboards.
  • Run structured reviews, approvals, escalations, and executive reporting.
  • Keep program practice consistent across subsidiaries and units.
  • Work with the PMO on project-level delivery and a clear view of the portfolio.

Program Budget & Resource Management

  • Hold the budgets, staffing plans, and forecasts for each program.
  • Track program spend, financial results, and budget swings.
  • Spread people, technology, and money sensibly across programs.
  • Assess business cases, costs against benefits, returns, and benefits delivered.
  • Manage outside consultants, contractors, tech vendors, and delivery partners.

Digital & Business Transformation Programs

  • Lead cross-team programs in digital change, automation, AI, cloud, and modernizing core systems.
  • Bring in online insurance platforms, client self-service portals, CRM, and tools for investment clients.
  • Partner with the CIO, CTO, CDO, and business heads so technology adds value.
  • Oversee process redesign, operational improvements, and change management.
  • Track adoption, how well rollouts work, and long-term results.

Risk, Compliance & Quality Management

  • Spot and manage operational, financial, regulatory, and tech risk at program level.
  • Keep programs within insurance, investment, financial-services, and governance rules.
  • Partner with the risk, legal, compliance, and audit teams.
  • Set up mitigation, contingency, and escalation plans.
  • Check quality and make sure outputs meet the agreed standards.

Stakeholder & Executive Management

  • Agree program priorities with the CEO, Board, executives, and unit heads.
  • Keep sponsors, program managers, and key stakeholders talking and working together.
  • Handle relationships with regulators, consultants, partners, and vendors where needed.
  • Settle disputes over scope, resources, timing, and competing priorities.
  • Report progress, finances, key risks, and recommendations to senior leaders.

Leadership & Program Management Excellence

  • Manage and coach everyone delivering programs, from directors down to project teams.
  • Build a strong program function with clear ownership and performance standards.
  • Set up training, mentoring, and career development.
  • Standardize program methods and keep improving them.
  • Add tools and reporting that give better visibility, coordination, and delivery.

3. Required Qualifications

  • A bachelor's in business, finance, project management, engineering, IT, or a similar field.
  • An MBA or master's in program management, strategy, finance, or a related area is a plus.
  • 12–15+ years in program or portfolio management, transformation, or strategic delivery.
  • At least five years at a senior level running big programs made up of many projects.
  • Insurance, reinsurance, banking, asset or wealth management, or wider financial-services experience preferred.
  • A history of delivering complex cross-team programs with measurable results.
  • Strong grasp of governance, delivery methods, budgeting, risk, and resource planning.
  • Has built or led an enterprise program office.
  • Comfortable with several delivery methods (Agile, Waterfall, PRINCE2, PMI, or a mix).
  • A strong leader and planner who communicates well, manages stakeholders, and solves problems.

Preferred Certifications:

  • PgMP (Program Management Professional)
  • PMP (Project Management Professional)
  • PfMP (Portfolio Management Professional)
  • PRINCE2 Practitioner
  • An Agile or Scrum certification

4. Key Performance Indicators (KPIs)

  • How many key programs land on schedule and within cost.
  • Results measured against the approved strategic goals.
  • Milestones and outputs achieved.
  • Budget variance and how resources are used.
  • Benefits delivered and ROI.
  • How well links between projects are managed.
  • How well risks are reduced and issues resolved.
  • How happy stakeholders are and how useful leadership reports are.
  • Sticking to the agreed governance and reporting rules.
  • Transformation programs (digital, operational, business) that land well.
  • Fewer delays, cost overruns, and delivery risks.

About TheHiveCareers

TheHiveCareers is a Caribbean jobs and skills platform, founded in 2020 by engineer and entrepreneur Melarka Williams. It matches professionals across the region with remote roles at employers abroad and in the Caribbean, using AI-based matching, and adds skills training and certification so candidates can grow while they work. Most listings here are full-time remote roles open only to residents of a named Caribbean country.

Employee benefits

Flexible work arrangements

Offers flexible working hours and arrangements to support work-life balance.

Comprehensive healthcare benefits

Provides comprehensive healthcare coverage for employees.

Remote work

Operates with a remote-first or hybrid model, allowing employees to work from various locations.

Skills and Training

Access to over 400 online courses and international certifications to support career growth.

Tech stack

  • Kubernetes
  • Spring Boot
  • Java
  • Docker
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