Head of Disputes

About the role

This role grants full ownership of the end-to-end disputes function at Cardless, requiring deep accountability for operational performance, quality, and strategic evolution of dispute handling. The hire will act as the definitive expert on disputes across all card programs, driving outcomes and setting the standard for accuracy and efficiency. You will establish the foundational structure, processes, and culture of the in-house disputes operation from the ground up. This position demands intense curiosity and the humility required to learn intricate network rules and partner dynamics quickly. Success is defined by your ability to transform a reactive external process into a scalable, automated, and strategically aligned function that protects the business and enhances trust.

Key facts

What you'll do

Investigate and audit the current business process of external BPO providers handling disputes to pinpoint failures in accuracy, adherence to timelines, and chargeback ratio performance indicators.

Design, document, and implement a comprehensive framework of policies, standard operating procedures, and decision trees that govern merchant disputes, billing errors, and fraud claims for multiple card programs.

Collaborate directly with the Engineering team to identify, prioritize, and implement automation solutions targeting manual tasks in evidence gathering, data validation, and status notification workflows.

Execute complex disputes from initiation to resolution, managing the full lifecycle involving evidence collection, strategic decision-making, formal network submission, and meticulous documentation.

Establish and monitor key performance indicators such as provisional credit accuracy, response SLA compliance, and chargeback ratios to ensure the operation meets rigorous internal and regulatory benchmarks.

Interpret and ensure strict compliance with Regulation E, Regulation Z, and card network rules, translating complex regulatory language into actionable guidance for the internal team.

Partner with the Fraud and Compliance departments to analyze dispute data, identify emerging risk patterns, and develop preventative strategies that reduce volume and improve outcomes.

Build and maintain productive working relationships with banking partners and network representatives to facilitate efficient communication and resolve interpretive disagreements.

Develop internal tools and dashboards that provide real-time visibility into dispute status, aging, and outcomes, thereby improving transparency and decision speed.

Mentor and coach the existing team on best practices, quality standards, and procedural rigor to elevate the collective capability in handling high-volume dispute scenarios.

Requirements

You must possess a proven track record of managing complex disputes within a financial services environment, demonstrating deep knowledge of chargeback representment and remediation.

You must have extensive experience navigating the specific regulations of Reg E and Reg Z, applying them correctly to ensure consumer protection and legal compliance.

You must hold a thorough understanding of Visa, Mastercard, and American Express dispute rules, timelines, and evidence requirements across multiple card networks.

You must have a history of working effectively with external vendors and BPOs, managing performance, and driving improvements in outsourced operations.

You must be capable of interpreting ambiguous situations and constructing logical decision trees where no existing playbook currently exists.

You must demonstrate strong written and verbal communication skills necessary for interacting with internal stakeholders and external banking partners.

You must exhibit a high degree of ownership and comfort operating independently in a fast-paced, startup environment with minimal direct supervision.

You must be detail-oriented and methodical, ensuring accuracy in complex cases that involve significant financial liabilities and regulatory scrutiny.

Nice to have

Experience building and managing a team in a disputes or customer recovery environment.

Background in developing automated dispute resolution workflows using rules engines or similar technologies.

Familiarity with AI applications for evidence summarization or fraud pattern detection in financial transactions.

Practical notes

Work is remote-first with a requirement to work in the San Francisco office 5 days a week.

Travel is not required for this role.

This role is eligible for an experienced hire who can start immediately.

Candidates must be authorized to work in the United States without sponsorship.