Head of Operations Overtime.ai

The Head of Operations at Overtime.ai is responsible for operational execution, client deployment, regulatory coordination, and day-to-day management of the platform in regulated collections and receivables environments. The role involves ensuring effective implementation, compliance, and client outcomes in a fast-moving, regulated industry.

Location: Remote (US)

Responsibilities

• 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
• 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
• 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
• 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
• 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
• 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
• 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
• 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

Benefits

• 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)