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R2

Senior Tax Analyst (LatAm Only)

Posted 13 Days Ago
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In-Office or Remote
Hiring Remotely in Chicago, IL
Senior level
In-Office or Remote
Hiring Remotely in Chicago, IL
Senior level
Manage tax compliance, reporting, payments, tax authority communications, transfer pricing, treaty treatment, thin capitalization, tax projections, and ERP tax configuration across multiple Latin American jurisdictions and the United States. Partner with BPO providers, external advisors, Legal, Finance, and Growth teams to improve tax processes, support new products and markets, and ensure timely, accurate documentation and filings.
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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). We are a tight-knit team coming from organizations such as Google, Amazon, Nubank, Uber, Capital One, Mercado Libre, Globant, and J.P. Morgan. We are entering a new phase of growth following a strategic investment from Ant International, focused on rapidly expanding our partner footprint, strengthening our credit and underwriting capabilities, and scaling our operations across multiple markets.

As a Senior Tax Analyst (IC3) you will play a key role in improving tax compliance and efficiency across R2’s operations in Mexico, Chile, Colombia, Peru, Brazil, Cayman and the USA, while supporting the company’s growth into new products and markets.

What you’ll work on

  • Review monthly tax compliance obligations in Brazil, Colombia, Peru, Chile and Mexico (VAT, income tax and withholding taxes, among others), working with our BPO providers to adjust procedures and improve timing, accuracy and documentation.
  • Own the regional tax obligations calendar and tax payments control, ensuring deliverables are on time and that tax files and supporting documents are organized by tax type and country.
  • Monitor the tax authorities’ electronic mailboxes in all countries, analyzing notices and information requests and coordinating timely responses with the Tax Manager and external advisors.
  • Configure and optimize the tax setup of our ERP as a whole, including electronic invoicing, withholding tax documents and other tax supporting documents, becoming the owner of these processes from a tax perspective.
  • Review the group’s transfer pricing policies and calculations, ensuring adherence to the arm’s length principle and that documentation and filings are complete and timely.
  • Ensure the correct tax treatment under double tax treaties for cross-border payments, including applicable withholding tax rates, tax residence certificates and supporting documentation.
  • Calculate and control thin capitalization and interest limitation (earnings stripping) rules across the group, assessing their impact on the deductibility of financing costs.
  • Work on tax projections for the group, estimating the tax impact of the business plan to support budgeting and decision-making.
  • Support the tax strategy for new products and market expansion, and drive tax planning and compliance projects with high impact on the company’s goals, partnering with Legal, Finance and Growth teams.

Who you are

  • You hold a Bachelor’s degree in Accounting, Law, Economics, Business Administration or a related field; a specialization in taxation is a plus.
  • You have 5+ years of tax experience, ideally combining Big 4 and multinational.
  • You have knowledge of transfer pricing and tax compliance obligations; you don’t need to have worked hands-on with every topic above.
  • You want to work in a multi-jurisdictional environment, dealing with different tax systems, languages and cultures every day.
  • You have advanced English skills (written and spoken) and feel comfortable working in an international environment. Spanish is a strong plus.
  • You are highly organized and detail-oriented, able to manage multiple deadlines and tax obligations across different countries.
  • You are proactive and take ownership, anticipating risks and communicating clearly with stakeholders when something requires attention.
  • You have strong analytical skills and advanced Excel, and are comfortable working with accounting data and ERP systems (NetSuite is a plus).

What We Offer

  • The chance to join a high-impact, mission-driven fintech.
  • Ownership and impact in a fast-paced, growth-oriented startup.
  • Cross-functional collaboration with exceptional teams.
  • Exposure to complex regulatory challenges and innovation in embedded finance.


Location: São Paulo, Santiago, Buenos Aires or Bogotá. 

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