Tax Specialist Lead

At R2, we believe that small and medium businesses are the productive engine of society. Small and medium businesses (SMBs) make up over 90% of companies in Latin America, yet they face a trillion-dollar credit gap. Our mission is to unlock SMBs’ potential by providing financial solutions that are tailored to their needs. We are reimagining the financial infrastructure of Latin America - where SMBs financial needs are satisfied without ever having to go to a bank.

R2 enables platforms in Latin America to embed financial services that SMBs can then leverage (starting with revenue-based financing and buy now pay later for business customers). We are a tight knit team coming from organizations such as Google, Amazon, Nubank, Uber, Capital One, Mercado Libre, Globant, J.P. Morgan, and Ualá. We are backed by world-class investors such as Gradient Ventures (Google’s AI-focused fund), COMETA, General Catalyst, Hi Ventures, Y Combinator, Femsa Ventures, Prosus, Endeavor Catalyst, among others.

We’re looking for a Tax Lead to oversee and manage R2’s tax strategy and compliance across Latin America. This is a senior individual contributor role with managerial scope and cross-functional influence, responsible for ensuring the company’s tax efficiency, compliance, and scalability as R2 continues to expand regionally. The Tax Lead will collaborate closely with external advisors, accounting, finance, legal, and operations teams to manage the tax implications of new products, capital structures, and cross-border transactions.

Responsibilities

• TAX STRATEGY & STRUCTURING

  • 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.

• TAX COMPLIANCE, GOVERNANCE & BPO MANAGEMENT

  • 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.

• TRANSFER PRICING & CROSS-BORDER TAXATION

• 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.

• ADVISORY & COLLABORATION

  • 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.
• Hands-on, owner mentality with strong interpersonal and stakeholder management skills.

Location: São Paulo - Brazil, Buenos Aires - Argentina, Santiago - Chile and Bogotá - Colombia will also be considered.