Director of Tax Planning & Advisory

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The Director of Group Tax Planning & Advisory will serve as SiriusPoint Group’s global lead for tax and transfer pricing research, planning, and advisory matters. This role is responsible for identifying, analyzing, documenting, and resolving complex tax issues and risks with technical rigor, attention to detail, sound judgment, and clear communication. The Director will support strategic planning, structuring, transaction execution, financial reporting, tax return positions, and SOX-related documentation by providing timely, well-supported advice to the Group Tax Director, senior management, finance teams, and business stakeholders.

Your responsibilities will include (1) identifying, thoroughly understanding, managing, and ultimately resolving technical tax issues, problems, and risks through a dynamic project-management approach, including maintaining clear ownership, timelines, issue trackers, analyses, conclusions, and resolutions, (2) proactively collaborating with colleagues across tax, legal, finance, investments, and the business to surface facts, align on workstreams, and drive decisions, (3) tactically managing external tax advisors by setting scope, directing technical work, challenging assumptions, tracking deliverables, and integrating advice into practical recommendations, (4) investigating and deeply understanding the applicable tax laws and relevant facts at a granular level, (5) ensuring that analyses are technically and factually complete, organized, and decision-ready, and (6) effectively communicating analyses, conclusions, status updates, open questions, and next steps to colleagues verbally and in writing in a manner that is clear, well understood, and timely.

Your responsibilities will include:

• Serve as a senior technical expert on tax laws and issues that materially affect SiriusPoint Group and its subsidiaries, with a focus on the U.S., Bermuda, Europe, Pillar II, and other key jurisdictions; apply that expertise to planning, compliance, and risk management.
• Develop and apply technical knowledge across relevant U.S. and non-U.S. tax frameworks, including BEAT, PFIC, Subpart F, the Tax Cuts and Jobs Act, One Big Beautiful Bill Act, treaty matters, federal excise tax, permanent establishment risk, Pillar II, and the Bermuda Corporate Income Tax Act. While pre-existing expertise in these technical areas is helpful, the successful candidate must be able to quickly learn and apply other technical frameworks (both U.S. and non-U.S.) to complex fact patterns, given the dynamic nature of tax laws and SiriusPoint Group’s global structure.
• Proactively partner with business, finance, investments, legal, and external advisors to tax-optimize transactions, investments, financial reporting, compliance, and SiriusPoint Group’s global legal and operating structure; organize workstreams, clarify ownership, and drive practical next steps through completion.
• Research, develop, and recommend tax-optimized transactional structures, and lead or manage tax due diligence related to M&A transactions, capital markets activities, and internal restructurings.
• Recommend new or improved transactional, legal, and operating structures to the Group Tax Director and senior management.
• Bring strong technical expertise, transaction execution experience, commercial awareness, sound risk judgment, and a collaborative, organized, and responsive working style that keeps complex, multi-party projects moving in a disciplined and transparent manner.
• Assess tax risks and contingencies in accordance with US GAAP (ASC 740) and IFRS to ensure adequate tax reserves are booked.

Global Transfer Pricing: Lead and manage SiriusPoint Group’s transfer pricing function for intercompany reinsurance, financing, services, and other cross-border arrangements. This will include:

• Design, structure, optimize, and execute new intercompany transactions and business operating models.
• Coordinate with internal stakeholders and tactically manage external transfer pricing advisors by defining scope, timelines, information requests, review cycles, and deliverables needed to develop, support, and document arm’s-length pricing for tax return positions.
• Develop and implement best practices for transfer pricing reporting, including Country-by-Country reporting, Master File, Local File, and other jurisdictional requirements, in coordination with the tax reporting and compliance function.
• Monitor intercompany transactions and regulatory developments, including BEPS-related changes, and assess the need for transfer pricing reports and supporting documentation.

Tax Controversy: Assist with international, federal, state, and local tax controversies, including audit coordination and resolution of technical issues, while representing SiriusPoint Group’s interests and supporting timely resolution.

Collaboration and Communication:

• Tactically manage and supervise external technical advisors, including Big 4 accounting firms and select law firms, by setting clear objectives, providing facts and context, coordinating workplans, reviewing outputs critically, resolving open questions, and ensuring advice is delivered in a form that supports timely business decisions.
• Proactively collaborate with tax, finance, legal, and other colleagues to gather facts, resolve dependencies, and calculate, support, and document financial reporting positions.
• Maintain dynamic issue trackers and tax files covering open matters, owners, timelines, assumptions, facts, advisor input, decisions, follow-ups, resolutions, memoranda, workpapers, correspondence, and supporting documents.
• Prepare or supervise technical memoranda that clearly support tax positions and allow the broader tax team, senior stakeholders, and external auditors to understand the basis for conclusions.

Your skills and abilities should include:

• 8-12 years of relevant tax experience, including experience within a major law or accounting firm and the insurance and/or financial services industry
• Hands-on corporate tax planning and transactional experience
• Juris Doctorate is required. Tax LL.M. and New York State bar admission are helpful but not required.
• Highly organized, with demonstrated ability to manage multiple complex matters, maintain issue trackers, document progress and resolutions, and follow matters through completion.
• Ability to communicate complex tax concepts clearly and effectively to both technical and non-technical audiences, including status, open questions, decisions, follow-ups, and final resolutions.
• Experience using Microsoft Word, PowerPoint, and Excel. Ability to learn and adapt to new technologies and software applications as needed.
• Strong analytical and reasoning abilities
• Ability to work independently with a roll-up-your-sleeves work ethic.
• Self-starter with the ability to adapt easily to change.
• Fluency in English is required.
• Travel may be required from time to time.

We aim to retain and attract great people, knowing they can achieve a rewarding and enriching career. We offer a competitive and above market compensation package.  The following are some of the benefits and perks we offer our employees:

• Medical
• Dental
• Vision
• FSA Medical and Dependent care
• Health Savings Account (HSA)
• EAP
• Basic Life and AD&D (company paid)
• 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
• Pet Insurance
• Tuition reimbursement
• Generous PTO
• Flexible work arrangement
• Fully stacked pantry on-site
• Team outings
• ERG Groups

Our CCPA Job Applicant Policy is found here: Sirius-America-CA-Job-Applicant-Privacy-Policy-Final.pdf

SALARY RANGE 250000 - 270000 USD