Head of Compliance Testing

Bermuda-headquartered with offices in New York, London, Stockholm and other locations, we are listed on the New York Stock Exchange (SPNT). We have licenses to write Property & Casualty and Accident & Health insurance and reinsurance globally. Our offering and distribution capabilities are strengthened by a portfolio of strategic partnerships with Managing General Agents and program managers. With over $3.0 billion total capital, SiriusPoint’s operating companies have a financial strength rating of A from AM Best, Fitch and S&P, and A3 from Moody’s.

Bermuda-headquartered with offices in New York, London, Stockholm and other locations, we are listed on the New York Stock Exchange (SPNT). We have licenses to write Property & Casualty and Accident & Health insurance and reinsurance globally. Our offering and distribution capabilities are strengthened by a portfolio of strategic partnerships with Managing General Agents and program managers. With over $3.0 billion total capital, SiriusPoint’s operating companies have a financial strength rating of A from AM Best, Fitch and S&P, and A3 from Moody’s.

Join Our Team We are looking for Test Manager to work closely with our Ceded Outwards Reinsurance Transformation team to drive technology implementation testing for our Global Ceded function. As the Test Manager for the Ceded Re Transformation programme, you will report directly to the VP, Reinsurance Product lead with dotted line into the Business Product Owner who is the Global Head of Ceded Reinsurance. You will work closely with senior Ceded Reinsurance SMEs, wider business stakeholders, data and enterprise architects, and dedicated delivery teams. There will also be indirect reporting responsibilities to the Transformation and Change Director via the EPMO. The successful candidate will have experience driving end-to-end testing for a complex transformation program involving business processes, technology platforms, data, integrations, reporting, and third-party solutions. The Test Manager will be accountable for the overall testing strategy, planning, coordination, governance, execution oversight, defect management, and testing readiness across the program. This individual will serve as the primary point of coordination between business stakeholders, technology teams, vendors, subject matter experts, and project leadership for all testing activities. The role will require flexibility in terms of working hours to accommodate working with US and UK time zones a minimum of 2 days per week (e.g., early start if EST time zone, starting at 7am or working to 7pm/8pm some evenings if working GMT time zone). This is a contract position. We are open to setting this up as a day rate contract at ~$950-$1,200 per day 1099-NEC / £700-£850 per day outside IR35 due to the specialist nature of the engagement. Your Responsibilities Will Include Test Strategy & Planning Develop, maintain, and execute the overall program test strategy and master test plan.

Define testing scope, objectives, phases, entry and exit criteria, timelines, dependencies, and governance.

Coordinate applicable testing phases, including system testing, integration testing, regression testing, user acceptance testing (UAT), data validation, operational readiness testing, end–to‑end testing, and performance testing.

Align testing milestones with the overall program and implementation plan.

Identify testing resource requirements and coordinate availability across business and technology teams.

Identify and proactively manage testing risks, assumptions, issues, and dependencies.

Test Preparation Lead development and review of test scenarios, test cases, expected results, and supporting documentation.

Establish traceability between business requirements and testing coverage.

Ensure appropriate coverage of end‑to‑end business processes, integrations, data flows, reporting, controls, exception scenarios, and downstream impacts.

Coordinate test data requirements and test environment readiness.

Establish and monitor readiness criteria before testing phases begin.

Test Execution Lead and coordinate day‑to‑day execution of testing activities.

Coordinate testing across business users, technology teams, third‑party vendors, and subject matter experts.

Identify and escalate issues that may affect testing timelines, or implementation readiness.

Defect Management Establish and manage the project's defect management and triage process.

Escalate critical or aging defects that may impact implementation.

Provide transparency regarding residual defects and associated implementation risk.

UAT & Business Acceptance Coordinate User Acceptance Testing across relevant business functions.

Partner with business leads and subject matter experts to ensure appropriate test coverage.

Monitor UAT execution and resolution of outstanding issues.

Coordinate testing completion, acceptance, and formal sign‑off.

Governance & Reporting Provide clear, regular reporting on testing progress and readiness to project and program leadership.

Develop dashboards and status reporting covering execution progress, pass/fail rates, defects, risks, dependencies, and outstanding decisions.

Maintain comprehensive testing documentation and evidence.

Escalate resource, environment, data, dependency, or delivery issues affecting testing.

Provide an objective assessment of testing readiness ahead of implementation and production deployment.

Develop and maintain strong relationships with key stakeholders, including senior management and vendors – utilize prior experience of IT implementation projects when working with internal SMEs & external partners. Ensure adherence to project and change management policy and methodologies, as per PMO guidelines, whilst supporting best practice by sharing open feedback and opportunities to improve.

Required Demonstrated experience leading end‑to‑end testing within complex technology, business, or transformation programmes, including test strategy, planning, execution, defect management, and UAT.

Strong understanding of system, integration, regression, end‑to‑end, data, and user acceptance testing across multiple systems, interfaces, and business processes.

Experience managing test dependencies involving environments, data, integrations, releases, and third‑party solutions.

Strong planning, organisation, risk‑management, analytical, and problem‑solving skills, with the ability to manage multiple workstreams, priorities, resources, and deadlines.

Proven ability to lead and coordinate business, technology, vendor, and subject‑matter teams across geographies and time zones without direct reporting authority.

Excellent written, verbal, presentation, and stakeholder‑management skills, including the ability to communicate complex testing issues, status, and risks clearly at working and executive levels.

Preferred Experience within insurance, reinsurance, or financial services, particularly testing financial, accounting, reconciliation, data, or reporting processes.

Experience supporting large‑scale system implementations with third‑party technology vendors or implementation partners.

Familiarity with test‑management and defect‑tracking tools.

Experience with SICS or other accounting platforms

Able to write basic SQL queries

Education and Foundational Knowledge Bachelor’s degree in business, finance, computer science, engineering, systems analysis, or a related field, or equivalent professional experience.

Working knowledge of insurance operations, including policy administration, underwriting, claims, financial reporting, compliance, and risk management.

Benefits Medical

Dental

FSA Medical and Dependent care

Health Savings Account (HSA)

EAP

Basic Long-Term Disability (employer) paid-Taxable income

Employee paid Long Term Disability (voluntary)

Company Medical Leave, Parental leave- 8 weeks full pay after 6 months of service

Voluntary benefits: short term disability, Critical illness, Hospital Indemnity, Accident

Travel assistance programs Company paid

401(k) 6 % safe harbor match, fully vested after two years, pre‑ and post‑tax contributions allowed

Gym reimbursement

Legal plan

Tuition reimbursement

Flexible work arrangement

Fully stacked pantry on‑site

The estimated day rate contract range for this position is mentioned below. United behind common goals At SiriusPoint we work as one team across our global business, and we unite that team behind common goals, understanding the positive impact we can all make at SiriusPoint. Our Purpose is to provide security and resilience in an uncertain world.

Our Vision is to be recognized as a best‑in‑class underwriter utilizing deep risk capabilities to protect our customers. Blending our talent, expertise, and data to provide intelligent risk solutions.

Our culture is one of performance and accountability. Customer Focused: Our customers are the reason we exist

Diversity: Diversity, inclusion and allyship make us stronger

Our Values - Integrity, Customer Focused, Solution Driven, Diversity, and Collaboration - are at the heart of our business, and they guide our everyday actions and decision making. We Achieve More Together At SiriusPoint, we know that diversity, inclusion and allyship make us stronger. We value and are committed to supporting the unique voices, backgrounds, cultures, lifestyles, and contributions of the diverse global employee base that make up our business.

SiriusPoint’s Talent Acquisition Team values the candidate experience at every stage. It has come to our attention that individuals may be impersonating SiriusPoint recruiters in an effort to obtain money or personal information from job seekers. Please be advised that official communications from SiriusPoint recruiters will originate from authorized SiriusPoint email accounts (ending in @siriuspt.SiriusPoint Will Never Request payment, checks, wire transfers, banking information, or financial account credentials as a condition of employment.

Ask candidates to purchase equipment on our behalf.

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SiriusPoint conducts interviews through recognized business communication channels and does not make employment offers without an appropriate interview and evaluation process. If you believe you have been contacted by someone posing as a SiriusPoint employee, please contact the Talent Acquisition team at View email address on click.appcast.io should also report the profile to LinkedIn using this online form: Contact form | LinkedIn Help. You may also report suspected fraud to the U.Federal Trade Commission at ReportFraud.ftc.gov or the FBI's Internet Crime Complaint Center at ic3.gov.

We are unable to sponsor or take over sponsorship of an employment visa at this time.

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