Head of Operations Overtime.ai

Acclaim AI has built Overtime.ai, a platform transforming receivables management through conversational AI and compliance-by-design automation. The market is at an inflection point: regulatory complexity is mounting, legacy collection models are losing effectiveness, and there's massive demand for modern, AI-first solutions. This is a leadership role to shape operations strategy and drive execution in a $20B+ market ready for disruption.

Overtime.ai is looking for a Head of Operations to own operational execution across implementations, client deployments, and regulatory compliance. You'll report directly to leadership and work across Product, Engineering, Compliance, Legal, and Client Success teams. This remote role based in Miami is a hands-on opportunity to build operational rigor inside a fast-scaling startup.

What you'll do

• Lead end-to-end deployment execution for collection agencies, healthcare organizations, and debt servicing clients, including onboarding, implementation coordination, and production launch readiness

• Establish operational processes, controls, escalation frameworks, and execution standards that maintain consistency and compliance across the platform

• Partner with Compliance and Legal to ensure all operational workflows align with FDCPA, TCPA, Reg F, state regulations, consent management, and other regulatory requirements

• Develop operational playbooks, QA processes, workflow governance standards, and deployment procedures that scale with company growth

• Track and report operational KPIs including deployment timelines, implementation success, workflow efficiency, client adoption, and operational risk indicators to executive leadership

• Act as the operational bridge across internal teams and external partners, coordinating priorities, dependencies, and deliverables during client implementations and platform releases

• Identify operational gaps and inefficiencies in live servicing environments, driving improvements focused on compliance, scalability, and client outcomes

What you'll bring

• 15+ years of operational leadership in collections, healthcare revenue cycle, financial services, contact center operations, or regulated servicing environments

• Deep working knowledge of debt collection regulations, operational compliance requirements, and consumer communication workflows

• Proven track record managing operational teams, large-scale implementations, onboarding programs, and client delivery functions

• Experience operating in high-volume, regulated environments with strong project management and organizational discipline

• Ability to coordinate across multiple functions (Compliance, Product, Engineering, Legal) and manage multiple priorities in fast-moving settings

• Experience supporting operational audits, governance processes, and escalation management

• Familiarity with AI-enabled workflows, conversational AI platforms, or contact center technologies is preferred

Nice to have

• Background supporting operational audits and governance frameworks

• Experience with automation platforms or AI-powered contact center tools

What We Offer

• Full-time remote position based in Miami, Florida

• Leadership role with direct impact on product strategy and company scale