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 RoleThe 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.Requirements15+ 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 preferredResponsibilitiesOperational Leadership & ExecutionLead 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 expansionsClient Deployment & Operational ReadinessOwn 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 stakeholdersCompliance & Regulatory CoordinationMaintain 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 standardsOperational Process ManagementDevelop 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 activitiesCross Functional CoordinationAct 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 environmentsClient & Partner ManagementServe as senior operational lead during implementations, client escalations, and strategic deploymentsManage relationships with operational leaders, compliance teams, implementation stakeholders, and external partnersSupport issue resolution, operational optimization, and client adoption effortsOperational Reporting & PerformanceTrack operational KPIs including deployment timelines, implementation success, workflow efficiency, client adoption, QA trends, and operational risk indicatorsDeliver operational reporting and execution updates to executive leadershipSurface operational risks, dependencies, and resource needs proactivelyOrganizational SupportHelp build operational structure, staffing models, and execution discipline as the company scalesSupport leadership with operational planning, prioritization, and resource coordinationEstablish repeatable operational processes that scale with company growthWhat We OfferA team built from the collections industry — work alongside leaders with experience across third party collections, healthcare revenue cycle, and first party servicing.Opportunity to grow with the company — take on meaningful responsibility as the business expands.Fast moving environment with direct access to leadership — decisions get made quickly and ideas can move into execution without unnecessary layers.Build technology tied to real operational outcomes — focused on improving recovery performance, lowering operating costs, and creating a better consumer experience in regulated environments.Fully remote within the US15 days PTO + all federal holidays + 3 sick days Health insurance reimbursement (ICHRA)401(k)Laptop provided by the companyParticipation in Employee Stock Ownership Plan (ESOP)Please mention the word DESIRABLE and tag ROjox when applying to show you read the job post completely (#ROjox). This is a beta feature to avoid spam applicants. Companies can search these words to find applicants that read this and see they're human.

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 RoleThe 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.Requirements15+ 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 preferredResponsibilitiesOperational Leadership & ExecutionLead 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 expansionsClient Deployment & Operational ReadinessOwn 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 stakeholdersCompliance & Regulatory CoordinationMaintain 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 standardsOperational Process ManagementDevelop 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 activitiesCross Functional CoordinationAct 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 environmentsClient & Partner ManagementServe as senior operational lead during implementations, client escalations, and strategic deploymentsManage relationships with operational leaders, compliance teams, implementation stakeholders, and external partnersSupport issue resolution, operational optimization, and client adoption effortsOperational Reporting & PerformanceTrack operational KPIs including deployment timelines, implementation success, workflow efficiency, client adoption, QA trends, and operational risk indicatorsDeliver operational reporting and execution updates to executive leadershipSurface operational risks, dependencies, and resource needs proactivelyOrganizational SupportHelp build operational structure, staffing models, and execution discipline as the company scalesSupport leadership with operational planning, prioritization, and resource coordinationEstablish repeatable operational processes that scale with company growthWhat We OfferA team built from the collections industry — work alongside leaders with experience across third party collections, healthcare revenue cycle, and first party servicing.Opportunity to grow with the company — take on meaningful responsibility as the business expands.Fast moving environment with direct access to leadership — decisions get made quickly and ideas can move into execution without unnecessary layers.Build technology tied to real operational outcomes — focused on improving recovery performance, lowering operating costs, and creating a better consumer experience in regulated environments.Fully remote within the US15 days PTO + all federal holidays + 3 sick days Health insurance reimbursement (ICHRA)401(k)Laptop provided by the companyParticipation in Employee Stock Ownership Plan (ESOP)Please mention the word DESIRABLE and tag ROjox when applying to show you read the job post completely (#ROjox). This is a beta feature to avoid spam applicants. Companies can search these words to find applicants that read this and see they're human.