Lead Tax Specialist

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October 17

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R2 Companies

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Real Estate

R2 Companies is a real estate investment and development firm with a focus on identifying and capitalizing on opportunities across various markets. The company operates multiple headquarters in Chicago, Minneapolis, and Milwaukee, emphasizing their strategic reach and presence in the Midwest of the United States. They engage with the community through various leasing and management services and maintain active communication channels via social media and newsletters.

11 - 50 employees

🏠 Real Estate

📋 Description

• Lead R2’s regional tax strategy, ensuring efficiency and compliance across Cayman, USA and all operating entities in Mexico, Chile, Colombia, Peru, and Brazil. • Provide strategic tax guidance for cross-border financing, capital injections, convertible notes, and corporate reorganizations. • Support the design of optimal legal and tax structures for new markets, product launches, and funding arrangements. • Collaborate with Legal and Capital Markets teams to assess the tax implications of contracts, shareholder agreements, and intercompany transactions. • Oversee the regional tax compliance process, managing the external BPO responsible for tax filings, accruals, and payments across jurisdictions. • Review and validate tax calculations, provisions, and filings prepared by the BPO to ensure accuracy, completeness, and adherence to local regulations. • Establish governance mechanisms, calendars, and review routines to monitor the BPO’s deliverables and performance. • Coordinate and review work performed by external tax advisors and local accounting firms. • Maintain internal controls and documentation standards to ensure compliance and audit readiness. • Monitor changes in local and international tax legislation, assessing their impact on R2’s operations. • Develop and maintain the company’s transfer pricing framework in line with OECD guidelines and local requirements. • Manage intercompany agreements, ensuring consistency with R2’s operating model and value chain. • Evaluate withholding tax exposures on cross-border service and financing flows, recommending mitigation strategies. • Act as the primary tax advisor to senior management on strategic initiatives, corporate structure changes, and funding transactions. • Partner with the Technical Accounting, FP&A, and Legal teams to integrate tax planning into business and financial models. • Support investor reporting, audits, and due diligence processes related to tax matters.

🎯 Requirements

• Bachelor’s degree in Accounting, Finance, Economics, or Law. • 5+ years of experience in tax planning and compliance, ideally within fintech, financial services, or Big 4 tax advisory. • Strong technical knowledge of corporate income tax, withholding taxes, and transfer pricing across Latin America. • Proven experience managing external tax BPOs and local advisors, ensuring quality, efficiency, and compliance. • Solid experience in cross-border structuring and advising on financing, equity, and debt transactions. • Understanding of IFRS principles and their interaction with tax accounting. • Excellent project management and stakeholder communication skills. • Full professional fluency in English and Spanish and/or Portuguese is a strong plus. • Previous experience in a high-growth fintech or startup environment is highly desirable.

🏖️ Benefits

• health insurance • retirement plans • paid time off • flexible work arrangements • professional development