Head of Operations Overtime.ai

ABOUT THE ROLE Overtime.ai, a cutting-edge platform transforming the debt recovery industry with AI-first technology, is seeking a seasoned leader to drive operational excellence. As the company's next major milestone, this role will play a critical part in shaping the future of receivables management. With a strong background in operations, compliance, and leadership, the successful candidate will be responsible for operational execution, client deployment, and regulatory coordination across the Overtime.ai platform. WHAT YOU'LL DO As the Head of Operations, you will oversee the operational execution of the platform, ensuring seamless implementation and day-to-day management across regulated collections and receivables environments. Your key responsibilities will include: - Leading operational execution across implementations, onboarding, client launches, and production environments - Establishing operational processes, controls, escalation paths, and execution standards across the organization - Driving accountability across internal teams and external partners to ensure operational consistency and execution discipline - Maintaining operational readiness for platform deployments, workflow changes, and client expansions - Owning deployment execution and operational coordination for collection agencies, healthcare organizations, debt buyers, and servicing clients - Building scalable onboarding, implementation, and operational support processes - Ensuring operational workflows align with client requirements, staffing models, servicing strategies, and compliance expectations - Maintaining strong working knowledge of debt collection regulations, including FDCPA, TCPA, Reg F, state regulations, consent management, disclosures, call handling, and operational controls - Partnering closely with Compliance and Legal teams to ensure operational processes align with regulatory expectations and client requirements WHAT YOU'LL NEED To succeed in this role, you will require: - 15+ years of operational leadership experience in collections, healthcare revenue cycle, financial services, contact center operations, or other regulated servicing environments - Strong understanding of debt collection regulations, operational compliance requirements, and consumer communication workflows - Experience managing operational teams, implementations, onboarding, and client delivery functions - Proven ability to operate inside regulated, high-volume servicing environments - Strong project management, organizational, and operational leadership skills - Experience coordinating across Compliance, Product, Engineering, Legal, and executive leadership teams - Ability to manage multiple priorities and operational risks in fast-moving environments - Experience supporting operational audits, governance processes, and escalation management - Familiarity with AI-enabled workflows, conversational AI, automation platforms, or contact center technologies preferred WHY REMOTE Overtime.ai offers a remote work opportunity, allowing you to work from anywhere while being part of a dynamic and innovative team. BENEFITS - Competitive salary - Opportunity to shape the future of receivables management - Collaborative and dynamic work environment - Professional growth and development opportunities