Head of Operations, Overtime.ai

Acclaim•Miami, FL

32d•Remote

About The Position

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

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