Monitoring and Testing Manager

We’re looking for a detail-oriented and independent compliance professional to build and execute monitoring and testing at Cardless. This role is responsible for assessing the effectiveness of our compliance controls across our credit card programs.

Cardless is a program manager that partners with FDIC- and OCC-regulated issuing banks to design and deliver co-branded credit cards. Our compliance team operates within this bank partnership model, which means your monitoring and testing work must account for obligations across multiple bank partners with different regulatory expectations. Understanding the program manager structure is key to succeeding in this role.

As a Monitoring & Testing Manager, you’ll design and execute ongoing control testing, identify gaps, validate remediation, and provide clear reporting to leadership and bank partners. You’ll work closely with Compliance, Risk, Operations, Fraud, and Customer Support to ensure our controls are not only well-designed but operating effectively in practice.

This is a high-ownership role for someone who enjoys digging into processes, challenging assumptions, and strengthening compliance infrastructure in a fast-moving fintech environment.

Execute and continuously improve a risk-based compliance monitoring and testing program covering BSA/AML, sanctions, complaints, marketing, and other regulatory requirements.

Adapt testing scope and methodology to account for obligations across multiple FDIC- and OCC-regulated bank partners, each with their own regulatory expectations, examination cycles, and reporting requirements.

Perform control testing to assess design and operating effectiveness, including transaction sampling, process walkthroughs, and data analysis.

Identify control gaps, root causes, and areas for improvement, and partner with stakeholders to develop practical remediation plans.

Track and validate corrective actions to ensure timely and sustainable resolution of findings.

Prepare clear, concise reporting for senior leadership and partner banks summarizing testing scope, findings, and remediation status.

Coordinate testing schedules and deliverables across bank partner examination timelines, ensuring each partner receives results and documentation aligned with their specific expectations.

Maintain testing documentation and workpapers that are organized, defensible, and audit-ready.

Conduct periodic risk assessments to inform the annual monitoring and testing plan.

Collaborate cross-functionally to ensure new products, features, and process changes are incorporated into the testing framework.

Stay current on evolving regulatory requirements and industry best practices, incorporating updates into the monitoring program.

Support first-line monitoring and testing efforts by coordinating with business units on control self-assessments and ongoing operational monitoring.

Support regulatory examination readiness and partner bank reviews by providing testing results, workpapers, and findings summaries as needed.

5+ years of experience in compliance monitoring, testing, internal audit, or risk management within banking, fintech, or credit card programs.

Strong understanding of BSA/AML, OFAC, UDAAP, and consumer compliance requirements.

Experience designing and executing testing programs, including control sampling and documentation.

Ability to translate regulatory requirements into practical control assessments.

Excellent analytical and writing skills, with the ability to clearly articulate findings and their impact on risk.

Strong attention to detail and organizational skills.

Proven ability to operate independently and manage multiple priorities in a fast-paced environment.

Comfort working cross-functionally and constructively challenging business partners when needed.

Commitment to integrity, objectivity, and regulatory excellence.

Experience working with partner banks in a fintech program management environment.

Familiarity with data analytics tools and automated control testing approaches.

Interest in leveraging technology to strengthen compliance oversight.

• We work in the office 5 days a week. We know that's a dealbreaker for some people, and that's okay.

• This is an early-stage company. We're ~40 people servicing hundreds of thousands of customers. You'll be building processes that don't exist yet, not optimizing ones that do. If you want structure handed to you, this isn't the right fit.

• You'll need to be highly self-directed. There isn’t a playbook for this role, and you won’t get daily check-ins. We’re looking for someone who sees what’s broken or missing, takes ownership, and follows through without being asked.

• The pace is intense and this role is hands-on. We have aggressive goals and a lot to build — this isn't a 9-to-5 quiet, maintenance-mode compliance job—you’ll be in the middle of everything.

• Build a compliance monitoring and testing program from the ground up. The framework exists, but you’ll turn it into a functioning, risk-based program with real test coverage.

• Work across multiple bank partner relationships with different regulatory frameworks, giving you broader exposure than a single-institution compliance role.

• High autonomy and direct ownership. You’ll shape how this function operates, not inherit someone else’s playbook.

• A clear path to grow with the function you’re building. As the program matures and the team scales, this role is positioned to grow with it.

We're headquartered in San Francisco, CA, with a beautiful office near the Transamerica building. This role is in-office 5 days a week.