Head of Operations, Overtime.ai

Description 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 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 Responsibilities Operational Leadership & Execution Lead operational execution across implementations, onboarding, client launches, and production environments Establish operational processes, controls, escalation paths, and execution standards across the organization Drive accountability across internal teams and external partners to ensure operational consistency and execution discipline Maintain 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 clients Build scalable onboarding, implementation, and operational support processes Ensure operational workflows align with client requirements, staffing models, servicing strategies, and compliance expectations Coordinate 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 controls Partner closely with Compliance and Legal teams to ensure operational processes align with regulatory expectations and client requirements Support audit readiness, documentation standards, complaint escalation management, and operational governance Ensure operational teams execute within approved compliance and workflow standards Operational Process Management Develop operational playbooks, deployment standards, QA processes, workflow governance, and escalation procedures Identify operational gaps, servicing inefficiencies, workflow risks, and process breakdowns Drive operational improvements focused on scalability, consistency, compliance, and client outcomes Coordinate 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 leadership Coordinate priorities, dependencies, risks, and operational deliverables across teams Ensure 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 deployments Manage relationships with operational leaders, compliance teams, implementation stakeholders, and external partners Support issue resolution, operational optimization, and client adoption efforts Operational Reporting & Performance Track operational KPIs including deployment timelines, implementation success, workflow efficiency, client adoption, QA trends, and operational risk indicators Deliver operational reporting and execution updates to executive leadership Surface operational risks, dependencies, and resource needs proactively Organizational Support Help build operational structure, staffing models, and execution discipline as the company scales Support leadership with operational planning, prioritization, and resource coordination Establish repeatable operational processes that scale with company growth What we offer A 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 US 15 days PTO + all federal holidays + 3 sick days Health insurance reimbursement (ICHRA) 401(k) Laptop provided by the company Participation in Employee Stock Ownership Plan (ESOP)