Senior Project Director

Company Description Checkbook is a U.S.-based fintech and digital payments company that provides businesses with flexible, efficient payment infrastructure to automate and scale cash flows through APIs. Its services include digital checks, ACH, RTP (Real-Time Payments), FedNow, Push to Card, virtual cards, paper checks, and bulk payments. Checkbook’s payment APIs and Marketplace solutions integrate directly into enterprise platforms, enabling organizations to send, receive, and manage funds with greater speed and convenience. The company focuses on modernizing business payments, reducing friction, and improving the overall payments experience for both businesses and their customers.
Role Description The Senior Project Director is a full-time remote role responsible for leading complex, cross-functional initiatives that support Checkbook’s payment infrastructure and API-based solutions. This role oversees project planning, execution, and delivery, ensuring alignment with strategic goals, timelines, and budgets. Day-to-day tasks include coordinating with product, engineering, operations, and client-facing teams; defining project scope and milestones; managing risks and dependencies; and tracking progress through clear metrics and reporting. The Senior Project Director will also drive stakeholder communication, facilitate decision-making, and provide leadership and mentorship to project managers and project teams. Additionally, this role contributes to improving project governance, refining processes, and supporting continuous improvement across programs and portfolios.
Qualifications
Experience in project and program leadership, including overseeing complex, multi-team initiatives, setting priorities, and managing timelines and budgets.
Background in fintech, financial services, or technology, with familiarity in digital payments, APIs, or enterprise integration projects.
Strong skills in stakeholder management, communication, and collaboration, with the ability to work effectively across technical and non-technical teams.
Proficiency with project management methodologies and tools (e.g., Agile, Scrum, Kanban, or hybrid approaches) and comfort with data-driven decision-making.
Ability to work independently in a remote setting, demonstrate sound judgment, and adapt to changing requirements in a fast-paced environment.
Experience leading and mentoring project teams or managers, fostering accountability, and promoting continuous improvement.
Bachelor’s degree in Business, Technology, or a related field; advanced degree or relevant certifications (e.g., PMP, PgMP, PMI-ACP, SAFe) are a plus.
Prior experience delivering large-scale technology or payments initiatives from inception through deployment and post-launch optimization.

Work arrangement
Yes