Head of Operations Overtime.ai
WFA Digital Insight
The demand for digital transformation in the debt collection industry is on the rise, with the market expected to reach $25B by 2026. As a result, companies like Acclaim AI are looking for experts who can navigate complex regulatory environments and drive operational excellence. With over 15 years of experience in collections, healthcare revenue cycle, or financial services, you can capitalize on this trend. Acclaim AI's Overtime.ai platform is poised to disrupt the industry, and the right candidate will have a unique opportunity to shape the go-to-market strategy and drive revenue growth. Before applying, consider the importance of operational discipline, compliance alignment, and client outcomes in this role.
Job Description
About the Role
The Head of Operations will be responsible for the day-to-day operational management of Overtime.ai, ensuring the platform is implemented effectively within regulated collections and receivables environments. This role requires strong operational knowledge of collections, healthcare revenue cycle, first-party servicing, and regulated consumer communication environments. The ideal candidate will have a deep understanding of operational risk, compliance expectations, client workflows, and the inner workings of collection agencies and servicing organizations.As a key member of the leadership team, the Head of Operations will work closely with cross-functional teams, including Operations, Compliance, Product, Engineering, Legal, Client Success, and executive leadership. The ability to manage multiple priorities and operational risks in fast-moving environments is essential, as is experience supporting operational audits, governance processes, and escalation management.
The role is highly strategic, and the successful candidate will be able to drive accountability across internal teams and external partners, ensuring operational consistency and execution discipline.
What You Will Do
- 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
What We Are Looking For
- 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
Nice to Have
- Experience with cloud-based technologies and SaaS platforms
- Knowledge of agile development methodologies and lean principles
- Certification in operational risk management or compliance
Benefits and Perks
- Competitive salary and benefits package
- Opportunity to work with a cutting-edge AI platform
- Collaborative and dynamic work environment
- Professional development and growth opportunities
- Flexible remote work arrangements
- Access to the latest technologies and tools
- Recognition and reward for outstanding performance
How to Stand Out
- Develop a strong understanding of debt collection regulations, including FDCPA, TCPA, and Reg F, to stand out as a candidate.
- Highlight your experience with operational risk management, compliance, and audit readiness to demonstrate your value.
- Showcase your ability to manage multiple priorities and operational risks in fast-moving environments.
- Be prepared to discuss your experience with AI-enabled workflows, conversational AI, and automation platforms.
- Emphasize your strong project management, organizational, and operational leadership skills to demonstrate your ability to drive accountability and execution discipline.
- Research the company culture and values to understand the importance of operational discipline, compliance alignment, and client outcomes.
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