Senior Compliance Analyst, Retail and Payments

Toast is driven by building the all-in-one restaurant platform that helps restaurants operate their business, increase sales, engage guests, and keep employees happy. The Toast Fintech Compliance Program provides a compliance by design embedded approach to compliance program management, with an emphasis on product lifecycle management, while enabling the business to innovate and deliver quality products and solutions to serve our customers. 

We are seeking a Senior Compliance Analyst to oversee compliance initiatives and management systems for our Retail and Payments business lines. Reporting to the Senior Manager of Payments & Retail Compliance, you will ensure alignment with industry regulations, card network rules, and internal risk policies. This role requires a proactive problem-solver who can navigate ambiguity, drive ownership, and collaborate cross-functionally to mitigate risk across Toast’s expanding operations.

Our Legal & Compliance teams are primarily concentrated in Boston, New York, Washington D.C., San Francisco, and Chicago. Candidates residing in these areas will be prioritized, as they will benefit from closer proximity to colleagues and greater access to company resources and events.

A day in the life (Responsibilities) 

• Own and execute key compliance management processes to monitor and ensure compliance with network and regulatory requirements across Toast Retail and Payments products
• Proactively manage and communicate status, risks, and next steps across multiple workstreams, ensuring stakeholders are informed without requiring prompting
• Assist in tracking and assessing new and changing regulations across Payments and Retail, including card network rules, data security standards, consumer protection laws, and emerging payment technologies; escalate potential concerns and support mitigation strategies
• Research and analyze compliance risks associated with retail merchants, including high-risk categories and evolving regulatory concerns
• Collaborate closely with Merchant Risk, Retail, Legal, Product, and Operations to develop and refine compliance policies, controls, and guidance
• Liaise with business partners to provide practical, risk-based compliance guidance, including process and control recommendations
• Support audits and regulatory inquiries by gathering documentation and ensuring transparency in compliance operations
• Execute and support internal compliance testing activities in partnership with the Global Testing Program Manager, including contributing to test planning, performing testing, documenting results, and tracking remediation to completion
• Evaluate and guide the business on new and existing product releases and enhancements to ensure alignment with applicable laws, regulations, policies, and strategic partner requirements
• Identify compliance issues (internally or through audits/exams), track remediation efforts, and follow up with stakeholders to ensure timely resolution
• Effectively manage competing priorities, flagging capacity constraints early and proposing solutions or reprioritization as needed
• Support the Retail business in adopting enterprise risk and compliance frameworks, including policies, training, and reporting

What you'll need to thrive (Requirements)

• Bachelor’s degree in business, finance, law, or a related field
• 3–5+ years of experience in compliance, risk management, or payment processing
• Familiarity with card network rules (Visa, Mastercard, etc.), regulatory frameworks (e.g., FinCEN, OFAC), and high-risk merchant categories
• Strong analytical skills with the ability to assess risk and identify potential compliance concerns
• Strong communication skills, with the ability to convey complex regulatory information clearly and concisely to both technical and non-technical audiences
• Ability to provide clear, structured updates on status, risks, and next steps to cross-functional partners and leadership
• Demonstrated ability to take ownership of work, operate proactively, and drive tasks forward with minimal direction
• Ability to work cross-functionally and build strong partnerships across Risk, Retail, Legal, and operational teams
• Ability to operate effectively in a fast-paced, dynamic environment and bring structure to ambiguous problems
• Ability to balance a collaborative, informal culture with a strong sense of urgency and accountability

Special Sauce* (Nice to Haves)

• Experience with compliance tools, transaction monitoring systems, or regulatory reporting platforms
• Experience in retail compliance
• Experience with fuel sales compliance
• Experience with international paymen