Senior Project Manager

ABOUT US | A leading regional player in the retail insurance sector, Coralisle Group Ltd., with over 600 employees and offices in Bermuda, the Bahamas, Barbados, the British Virgin Islands, the Cayman Islands, Turks & Caicos Islands, Anguilla, Antigua and Barbuda, Montserrat, Dominica, St. Lucia, St. Vincent, Saint Maarten, Grenada, Trinidad and Tobago, Guyana, Curacao, Aruba, Jamaica and Belize, we and offers a complete range of premier financial and insurance services to our individual and corporate clients. We know that our products make a real difference to our clients and their families.

THE ROLE | Reporting to the Director of IT Transformation, the Senior Project Manager will lead complex technology and business change initiatives from initiation through transition to operations. You will be accountable for integrated plans, delivery outcomes, budget and resource control, risk management, and clear decisions by sponsors and governance bodies. You will coordinate business teams, IT, vendors, and control functions to deliver agreed benefits while meeting applicable security, privacy, and regulatory requirements. You will also lead complex technology and business change initiatives from initiation through transition to operations.

• Own project initiation, scope, business case inputs, success measures, delivery approach, milestones, dependencies, and acceptance criteria with the sponsor and business owner.
• Develop and maintain integrated delivery plans across business processes, technology, data, testing, training, cutover, and operational readiness; adjust sequencing when constraints change.
• Lead cross-functional teams and external partners, assign accountable owners, remove impediments, and hold workstream leads to agreed commitments.
• Manage implementation, testing, migration, drive project to completion, escalates resource, capacity and capability, and handover with documented acceptance and a clear transition to support and benefits ownership.
• Establish proportionate project governance, decision rights, reporting cadence, and documentation in line with the IT PMO framework.
• Maintain transparent RAID and decision logs; escalates material threats early with options, impacts, and a recommended course of action.
• Control scope through impact assessment and formal change decisions covering cost, schedule, risk, quality, and benefits.
• Ensure security, privacy, compliance, architecture, procurement, and operational controls are engaged at the right points in the lifecycle; retain evidence for audit and oversight.
• Prepare and manage project budgets, forecasts, resource demand, and actual spend; explain variances and recommend corrective action.
• Coordinate vendor deliverables, dependencies, service obligations, and acceptance against contracts and statements of work; raise performance concerns promptly.
• Build working relationships with executive sponsors, business leaders, IT teams, vendors, and impacted users across jurisdictions.
• Provide concise, decision-oriented status reports and facilitate steering committees, workshops, and issue resolutions.
• Partner with business owners and change leads on communications, training, adoption, and measurable benefits realization.
• Coach project team members and contribute lessons learned, standards, and continuous improvement across the IT PMO.

THE PERSON | To be the ideal candidate you must have:

• PMP, PRINCE2 Practitioner, or equivalent professional certification preferred.
• Bachelor's degree in Computer Science, Information Technology, Business, or a related field, or equivalent relevant experience.
• 5–7 years of experience in a similar project management role, with responsibility for delivering complex technology and business change initiatives.
• Experience delivering technology-enabled changes in insurance or another regulated financial services environment is strongly preferred. Familiarity with policy, claims, billing, finance, or customer service processes would be an advantage.
• Strong command of predictive, agile, and hybrid delivery approaches, with judgment to select and adapt the approach to the work.
• General awareness of AI tools and their appropriate use, including key considerations such as data quality, privacy, security, accuracy, and human oversight. Experience supporting AI-enabled projects would be an advantage.
• Proven ability to influence senior stakeholders, facilitate decisions, manage conflict, and communicate clearly across technical and nontechnical audiences.
• Experience with financial forecasting, commercial and vendor management, and governance reporting.
• Working knowledge of change management, data and system integration, cybersecurity, privacy, and operational transition considerations.
• Proficiency with project planning, collaboration, and reporting tools; strong analytical, organizational, and problem-solving skills.

THE BENEFITS | We value our employees and offer a supportive and inclusive work environment. We provide opportunities for professional growth and development, competitive compensation, and a comprehensive benefits package.

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