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Chief Project 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 employeesJamaica only

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About the job

Chief Project Officer (CPO) – Insurance & Investments

1. Role Summary

Leads the strategic project portfolio, company-wide program management, and major transformation work across the insurance and investment businesses.

Makes sure strategic projects are planned, ranked, funded, run, and delivered in line with company goals. Oversees complex work in insurance operations, investment services, digital change, compliance, expansion, M&A, and operational improvement.

Partners with the CEO, Board, and senior team to set strong governance, make the most of resources, manage delivery risk, and get measurable results from project spending.

2. Key Responsibilities

Strategic Project & Portfolio Management

  • Create and run the company-wide project and portfolio strategy.
  • Select, assess, rank, and oversee strategic projects in the insurance and investment units.
  • Keep the portfolio in line with strategy, growth targets, and operating priorities.
  • Judge feasibility, business cases, resource needs, returns, and rollout risk.
  • Track portfolio results and make sure projects deliver their strategic and financial gains.

Insurance & Investment Project Delivery

  • Head initiatives across every line of business: life, general, reinsurance, investments, wealth, and other financial services.
  • Oversee product launches, policy administration systems, claims, underwriting, and distribution growth.
  • Where relevant, run investment initiatives such as portfolio systems, operations, client reporting, and service.
  • Coordinate regulatory change, process modernization, and restructuring.
  • Support new business models, financial products, and expansion.

Project Governance & PMO Leadership

  • Set up and oversee the PMO with its standards, methods, policies, and governance.
  • Introduce approval steps, stage-gate reviews, reporting, and escalation.
  • Keep project practice consistent across units and subsidiaries.
  • Track scope, schedule, budget, outputs, and quality.
  • Present portfolio results, major risks, and recommendations to executives and the Board.

Digital Transformation & Technology Projects

  • Lead technology rollouts and digital change throughout the organization.
  • Oversee FinTech, automation, AI, cloud, CRM, and enterprise-system projects.
  • Bring in online insurance platforms, client portals, mobile apps, and tools for investment clients.
  • Partner with the CIO, CTO, and CDO teams so tech projects meet business needs.
  • Watch tech spend, schedules, how systems connect, and uptake.

Financial & Resource Management

  • Set and control the money behind the portfolio.
  • Track spending, cost swings, financial results, and project profitability.
  • Share resources sensibly across projects, departments, and units.
  • Assess ROI, costs against benefits, and benefits delivered.
  • Manage outside consultants, contractors, tech vendors, and delivery partners.

Risk, Compliance & Quality Management

  • Spot and manage operational, financial, regulatory, and tech risks on projects.
  • Keep projects within insurance, investment, financial-services, and governance rules.
  • Partner with the risk, legal, compliance, and audit teams.
  • Put mitigation, contingency, and continuity plans in place for critical projects.
  • Make sure outputs meet quality standards and company requirements.

Business Transformation & Strategic Initiatives

  • Lead cross-team change aimed at efficiency and better business results.
  • Back reorganizations, M&A, joint ventures, and bringing merged businesses together.
  • Coordinate geographic expansion, entry into new markets, and diversification.
  • Drive process improvement, automation, and cost savings.
  • Track business gains and make sure project results are adopted.

Stakeholder & Executive Management

  • Set project priorities with the CEO, Board, executives, and unit heads.
  • Communicate with staff, regulators, investors, consultants, and partners where appropriate.
  • Resolve disputes over scope, budget, timing, and resources.
  • Give executives updates on performance, delivery problems, and recommendations.
  • Build strong relationships with key stakeholders so projects succeed.

Leadership & Team Development

  • Manage everyone who delivers projects, from directors to PMO staff.
  • Build strong delivery teams across several business units.
  • Make ownership and performance expectations clear and invest in people's growth.
  • Encourage ownership, teamwork, innovation, and high delivery standards.
  • Bring in project tools, dashboards, and performance measures.

3. Required Qualifications

  • A bachelor's in business, finance, project management, engineering, IT, or a similar field.
  • An MBA or master's in project management, finance, strategy, or a related area is a plus.
  • 12–15+ years in project, program, or portfolio management or enterprise transformation.
  • 5+ years in a senior leadership role over complex portfolios and strategic programs.
  • Insurance, reinsurance, banking, asset or wealth management, or wider financial-services experience preferred.
  • A record of delivering large multi-department projects on budget and on time.
  • Knows how insurers and investment firms work and what operating under regulation involves.
  • Has built and run enterprise PMOs and governance frameworks.
  • Comfortable with Agile, Waterfall, PRINCE2, PMI, and similar ways of delivering.
  • Skilled at planning finances, setting budgets, handling risk, and assigning resources.
  • An excellent leader and communicator, skilled at negotiation, analysis, and stakeholder management.

Preferred Certifications:

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

4. Key Performance Indicators (KPIs)

  • Share of strategic projects finished on time and budget.
  • Portfolio results and fit with strategy.
  • Cost and schedule variance.
  • Milestones and agreed outputs achieved.
  • ROI and benefits delivered.
  • Delivery of insurance and investment transformation work.
  • Risk and issue handling.
  • Compliance with PMO governance and reporting.
  • Resource use and team productivity.
  • How satisfied stakeholders are and how quality is rated.
  • Fewer delays, overruns, and delivery risks.
  • Digital and growth projects that land well.

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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