About Us: Checkbook is a FinTech company building modern payment infrastructure for businesses. We help clients send and receive payments (including check-based payments) through a single platform - designed to be reliable, transparent, and operationally sound as volume grows. The Role: We are hiring a Payment Operations Manager to own and scale our payment operations function. This role sits at the intersection of payments, risk, customer experience, and process design. You will keep payment flows running smoothly end-to-end while building the controls, workflows, and reporting that let the business scale with confidence. This is a hands-on leadership role. You will run day-to-day payment operations and partner closely with Product, Engineering, Risk and Fraud, Finance, and Customer Support to improve accuracy, speed, and customer outcomes. This position is fully remote (USA based). Responsibilities: Own day-to-day payment operations Own the end-to-end payment operations lifecycle, including transaction monitoring, reconciliation, settlements, refunds, disputes, and exceptions. Ensure accuracy, timeliness, and appropriate controls across payment flows Maintain clear operating rhythms (daily, weekly, and monthly) to keep the function disciplined and predictable. Monitoring, exceptions, and risk partnership Oversee monitoring of incoming and outgoing transactions to identify errors, anomalies, and potential risk. Partner with Compliance, Finance, and Customer Support to strengthen controls, identify repeat exception patterns, and reduce recurrence through durable fixes. Maintain disciplined, well-documented exception resolution, with root-cause analysis and prevention as the standard. Reconciliation and financial accuracy Lead daily, weekly, and monthly reconciliations across payment channels and internal systems. Investigate discrepancies, drive resolution with the right owners, and implement preventative controls to reduce recurrence. Partner with Finance on settlement procedures, reporting requirements, and control design. Process design, documentation, and readiness Identify gaps and failure points in existing workflows, then redesign for clarity, scale, and audit readiness. Create and maintain process documentation, runbooks, and operating procedures that stand up to scrutiny and survive growth. Support audits, partner reviews, and internal testing with strong evidence trails and clean operational execution. Customer experience and escalations Serve as an escalation point for complex payment issues impacting customers. Ensure payment-related inquiries are handled promptly, clearly, and with a high bar for accuracy and professionalism. Partner with Customer Support to improve tooling, macros, and workflows that reduce repeat issues and customer frustration. Reporting and operational insights Build and maintain reporting on volume, trends, exception rates, reversals, and operational performance. Use data to surface risks, prioritize fixes, and inform product and operational decisions. Provide leadership with clear, regular visibility into payment operations health and readiness. Cross-functional execution Partner with Product and Engineering on new payment features, launches, and system enhancements, bringing an operator’s perspective to requirements and testing. Lead operational rollout plans for new capabilities, including training, documentation, controls, and monitoring. About You: Bachelor’s degree in Finance, Business Administration, or a related field (or equivalent experience). Four or more years of experience in payment operations, financial operations, fintech, or a related domain. Strong understanding of payment processing systems, transaction lifecycles, and reconciliation workflows. Proven ability to manage complexity, prioritize well, and operate calmly in a fast-paced environment. Highly analytical, with strong attention to detail and a practical, problem-solving mindset. Comfortable owning processes end-to-end and improving them as the business scales. Strong communicator who can work effectively across technical and non-technical teams. Familiarity with regulatory and compliance considerations in payments is a plus. Experience working with payment platforms, processors, or payment operations tooling is a bonus. Benefits: Medical, dental, vision, long-term disability, and additional insurance programs 401(k) Equity Compensation: Competitive base salary, bonus, and equity (commensurate with experience) Location: Remote (USA) Equal Opportunity Employment Checkbook is an equal opportunity employer. We make employment decisions based on job-related qualifications and business needs, without regard to race, color, religion, sex (including pregnancy), sexual orientation, gender identity, national origin, age, disability, veteran status, or any other status protected by applicable law. If you need accommodation during the application process, please contact us directly.