Head of Operations Overtime.ai

Receivables management is a $20B+ market at an inflection point. Increasing regulatory complexity, rising operating costs, and declining effectiveness of legacy outbound models are driving demand for a modern, AI-first approach. Overtime.ai (Powered by Acclaim) is THE platform to define this next generation—combining voice AI, automation, and compliance-by-design to transform how the industry recovers debt while improving the consumer experience. This is a start-up leadership opportunity to shape go-to-market strategy, build a category-defining sales motion, and drive revenue in a market ready for disruption. About The Role The Head of Operations is responsible for operational execution, client deployment, regulatory coordination, and day-to-day operational management across the Overtime.ai platform. This role ensures the platform is implemented effectively inside regulated collections and receivables environments while maintaining strong operational discipline, compliance alignment, and client outcomes. This role requires deep operational knowledge of collections, healthcare revenue cycle, first party servicing, and regulated consumer communication environments. The ideal candidate understands operational risk, compliance expectations, client workflows, and how collection agencies and servicing organizations actually operate day to day. The role is highly cross-functional and works across Operations, Compliance, Product, Engineering, Legal, Client Success, and executive leadership teams. Requirements 15+ years of operational leadership experience in collections, healthcare revenue cycle, financial services, contact center operations, or other regulated servicing environmentsStrong understanding of debt collection regulations, operational compliance requirements, and consumer communication workflowsExperience managing operational teams, implementations, onboarding, and client delivery functionsProven ability to operate inside regulated, high-volume servicing environmentsStrong project management, organizational, and operational leadership skillsExperience coordinating across Compliance, Product, Engineering, Legal, and executive leadership teamsAbility to manage multiple priorities and operational risks in fast-moving environmentsExperience supporting operational audits, governance processes, and escalation managementFamiliarity with AI enabled workflows, conversational AI, automation platforms, or contact center technologies preferred Responsibilities Operational Leadership & Execution Lead operational execution across implementations, onboarding, client launches, and production environmentsEstablish operational processes, controls, escalation paths, and execution standards across the organizationDrive accountability across internal teams and external partners to ensure operational consistency and execution disciplineMaintain operational readiness for platform deployments, workflow changes, and client expansions Client Deployment & Operational Readiness Own deployment execution and operational coordination for collection agencies, healthcare organizations, debt buyers, and servicing clientsBuild scalable onboarding, implementation, and operational support processesEnsure operational workflows align with client requirements, staffing models, servicing strategies, and compliance expectationsCoordinate implementation activities across Product, Engineering, Compliance, Legal, and client stakeholders Compliance & Regulatory Coordination Maintain strong working knowledge of debt collection regulations including FDCPA, TCPA, Reg F, state regulations, consent management, disclosures, call handling, and operational controlsPartner closely with Compliance and Legal teams to ensure operational processes align with regulatory expectations and client requirementsSupport audit readiness, documentation standards, complaint escalation management, and operational governanceEnsure operational teams execute within approved compliance and workflow standards Operational Process Management Develop operational playbooks, deployment standards, QA processes, workflow governance, and escalation proceduresIdentify operational gaps, servicing inefficiencies, workflow risks, and process breakdownsDrive operational improvements focused on scalability, consistency, compliance, and client outcomesCoordinate operational testing, release readiness, and production support activities Cross Functional Coordination Act as the operational bridge across Operations, Product, Engineering, Compliance, Client Success, Sales, and executive leadershipCoordinate priorities, dependencies, risks, and operational deliverables across teamsEnsure product releases and workflow changes can be operationalized effectively in live environments Client & Partner Management Serve as senior operational lead during implementations, client escalations, and strategic deploymentsManage relationships with operational leaders, compliance teams, implem