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Group Head of Project Management Office (PMO) – 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 employeesAntigua and Barbuda only

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About the job

Group Head of Project Management Office (PMO) – Insurance & Investments

1. Role Summary

Leads project management for the whole Group, across every subsidiary, business unit, and market in its insurance and investment business.

Sets Group-wide governance, portfolio standards, delivery frameworks, and performance tracking so strategic and transformation projects land well. Acts as the single place where leaders can see every project's priority, cost, staffing, risk, links, and expected payoff.

Partners with the Group CEO, executive team, subsidiary CEOs, and business heads so every major project supports growth, efficiency, digital change, and long-term goals.

2. Key Responsibilities

Group PMO Strategy & Governance

  • Design and roll out the Group PMO's strategy, structure, and operating model.
  • Standardize methods, policies, procedures, and reporting in every subsidiary.
  • Set approval steps, stage-gate reviews, escalation routes, and accountability.
  • Keep portfolios in line with Group strategy and business priorities.
  • Apply the same standards and controls in every market and unit.

Strategic Project Portfolio Management

  • Steer every project in the Group, whether insurance, investment, corporate, or operations.
  • Rank and track strategic projects by value, financial effect, risk, and resource needs.
  • Follow progress, milestones, dependencies, budgets, timing, and outputs.
  • Flag weak projects and recommend fixes or moving resources.
  • Give leaders one combined view of how the portfolio is doing.

Insurance & Investment Project Oversight

  • Keep watch over Group insurance work: new products, underwriting, claims, policy admin, and sales channels.
  • Where relevant, track investment projects such as portfolio reporting, operations, wealth platforms, and client service.
  • Coordinate compliance, process modernization, and efficiency initiatives.
  • Support new financial products, business models, and expansion.
  • Keep projects within insurance, investment, financial-services, and governance rules.

Digital Transformation & Technology Projects

  • Govern Group-wide technology modernization and digital programs.
  • Coordinate rollouts of enterprise systems, CRM, automation, AI tools, and digital financial services.
  • Partner with the CIO, CTO, CDO, and business leaders on tech delivery.
  • Track integration, rollout risk, tech budgets, and uptake.
  • Make sure digital work measurably improves customer experience and operations.

Financial & Resource Management

  • Oversee Group-wide project budgets, forecasts, and spend tracking.
  • Watch cost performance and look for savings.
  • Share resources across subsidiaries, departments, and initiatives.
  • Assess business cases, costs against benefits, ROI, and expected gains.
  • Make good use of in-house staff, consultants, contractors, and partners.

Risk, Compliance & Quality Management

  • Create one Group-wide way to log and escalate project risks.
  • Monitor operational, financial, regulatory, tech, and rollout risks across portfolios.
  • Partner with the Group's risk, legal, compliance, and audit teams.
  • Keep projects within internal policy, governance, and regulation.
  • Have fallback and risk-reduction plans ready for the most critical work.

Performance Reporting & Benefits Realization

  • Build Group-wide dashboards, performance reports, and executive decks.
  • Check delivery against agreed scope, budget, schedule, milestones, and quality.
  • Track financial gains, operational improvements, and ROI.
  • Give the Group CEO, Board, and leadership committees regular portfolio updates.
  • Recommend interventions that improve execution and delivery.

Stakeholder & Subsidiary Management

  • Stay close to the heads of each subsidiary and unit, as well as sponsors and program leads.
  • Run Group steering committees and portfolio reviews.
  • Make sure subsidiaries and head-office teams plan and deliver in sync.
  • Manage consultants, tech vendors, contractors, and partners.
  • Keep communication, accountability, and reporting consistent across all Group companies.

Leadership & PMO Capability Development

  • Manage the whole Group PMO, from its directors to managers, analysts, and cost/schedule controllers.
  • Define PMO structures, roles, and reporting lines in each subsidiary.
  • Set up training, mentoring, and capability building.
  • Encourage accountability, openness, teamwork, and high standards.
  • Keep raising project management maturity across the organization.

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, strategy, finance, or a related area is a plus.
  • 12–15+ years in project, program, or portfolio management or enterprise transformation.
  • 5+ years leading a PMO across several units, subsidiaries, or large portfolios.
  • Background in insurance, reinsurance, banking, asset or wealth management, or diversified financial services.
  • Has built or led an enterprise or group-level PMO.
  • Strong in portfolio governance, finance, resource planning, risk, and execution.
  • Has run complex programs spanning several countries or entities.
  • Knows PMI, PRINCE2, Agile, Waterfall, and hybrid methods.
  • Strong leadership, executive communication, stakeholder skills, negotiation, and analysis.

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 Group projects finished on time and on budget.
  • Portfolio results against Group strategy.
  • Cost and schedule variance.
  • Compliance with Group PMO governance and reporting.
  • Landing the big insurance and investment projects.
  • Risk spotting, mitigation, and escalation.
  • Resource use across subsidiaries.
  • Benefits and ROI from major projects.
  • Accurate, timely consolidated reports.
  • Satisfaction across Group companies.
  • Rising project maturity in subsidiaries.
  • Fewer delays, 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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