Head of Disputes & AI Operations

Casap is a Series A startup that has raised over $30M from Emergence, Lightspeed, and Primary Ventures. Based in San Francisco, the company was founded by product leaders from Robinhood and Chime. We are on a mission to change the way banks operate by automating disputes and fighting friendly fraud. People love what we’ve built, from everyday users to the biggest names in finance.

We’re looking for a Head of Disputes & AI Operations to lead Casap’s dispute strategy and ensure our AI-powered workflows deliver exceptional outcomes for customers. This is a pivotal role that combines deep dispute expertise, operational leadership, and product-oriented thinking. You will be the go-to authority for dispute resolution best practices, guide how our AI adapts to each customer’s needs, and build scalable processes to maximize win rates and efficiency.

You’ll partner closely with our Product, Engineering, Customer Success, and Go-to-Market teams to set the standard for dispute excellence in the industry—ensuring Casap remains the most effective and trusted solution in the market.

• Own Casap’s Dispute Strategy by defining best practices, win-rate targets, and operational benchmarks that set the industry standard.

• Lead AI-Driven Optimization by collaborating with Product and Engineering to fine-tune AI models, customize decision logic, and automate workflows tailored to each customer’s requirements.

• Drive Customer Outcomes at Scale by ensuring every deployment delivers measurable ROI, improved win rates, and reduced operational costs.

• Build and Lead a High-Impact Team to support ongoing dispute analysis, AI tuning, and customer enablement—ensuring quality and consistency across accounts.

• Partner with Customers as a Strategic Advisor to align dispute strategy with business goals, compliance requirements, and network rules.

• Continuously Improve Performance by monitoring dispute results, identifying trends, and implementing playbooks that improve both efficiency and success rates across the portfolio.

• Shape Product Roadmap by translating customer needs, operational insights, and dispute trends into actionable product improvements.

• Represent Casap as an Industry Leader in disputes, automation, and AI-driven operations—both with customers and at industry events.

• 8+ years of experience in disputes, chargebacks, or fraud operations within banks, fintechs, card networks, or payments providers, with at least 3 years in a leadership role.

• Deep expertise in dispute resolution processes, card network rules, and chargeback management strategies.

• Proven ability to lead teams, define strategy, and scale operational excellence across multiple customers or regions.

• Experience working with AI, machine learning, or automation platforms in a production environment.

• Strong cross-functional collaboration skills, with the ability to work closely with technical and non-technical teams.

• Analytical mindset with experience using data to measure performance and inform strategy.

• Exceptional communication skills, with the ability to influence executives and inspire teams.

• Passion for building category-defining solutions and helping customers succeed.