Head of Operations, Overtime.ai

About the role

Overtime.ai (Powered by Acclaim) is transforming the debt collection industry with a modern, AI-first approach. This role offers a unique opportunity to shape the go-to-market strategy, build a category-defining sales motion, and drive revenue in a market ripe for disruption.

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
• 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