Head of Operations & Business Management

About Self Bill Pro: Self Bill Pro is a rapidly growing startup dedicated to solving one of the most persistent challenges in the employee benefits ecosystem: the complexity of monthly benefits billing. We provide a tech-enabled service where our dedicated team leverages proprietary software to eliminate the administrative burdens of manual invoice audits and costly billing errors. Our mission is to streamline this critical operation, freeing up employers, brokers, and carriers to focus on their strategic priorities.

The Director of Operations is responsible for overseeing and optimizing day-to-day business operations across the organization, with direct oversight of the Implementation, Client Services, and Data Operations functions. This role ensures operational efficiency, scalability, and alignment with company goals by driving process improvements, managing cross-functional workflows, and supporting team performance across these core business functions.

The Director of Operations partners closely with executive leadership to translate strategic priorities into actionable plans, while maintaining a strong focus on execution, quality, and continuous improvement. This is a director level, supervisory role that guides the managers leading each function, rather than performing hands on work within them.

Oversee daily operations across core functional areas, including Implementation, Client Services, and Data Operations

Provide leadership, coaching, and direction to the managers leading each of these functions

Establish, track, and analyze key performance indicators (KPIs) to measure operational and team performance across all three functions

Ensure operational compliance with HIPAA and carrier and vendor data handling requirements across all functions overseen

Implementation Oversight

Provide strategic direction over the Implementation function, ensuring the team maintains technical excellence in EDI standards (including HIPAA 834), API integrations, and benefit administration platforms

Partner with the Manager of Implementation to set priorities for process design, automation, and tooling that improve data exchange and issue resolution

Ensure quality standards and escalation processes are in place for complex integration challenges

Data Operations Oversight

Provide strategic direction over the Data Operations function, ensuring accuracy and auditability across plan premium audits, billing data analysis, and Excel-based reconciliation processes

Partner with the Manager of Data Operations to set standards for data quality, process automation, and tool development

Guide the team's approach to identifying trends, anomalies, and discrepancies in billing data, ensuring consistent resolution, documentation, and training for junior team members

Partner with the Manager of Client Services to ensure a consistent, high-quality client experience across all touchpoints

Support escalation management for complex or high-impact client issues

Lead resource planning and capacity management to support business growth and delivery timelines

Maintain high standards of service delivery, quality, and client satisfaction

Drive continuous improvement initiatives and foster a culture of accountability and performance

• 15+ years of experience in operations, business management, or a related field, including meaningful experience in benefits administration, EDI/API implementation, or billing and data operations
• 8+ years of experience leading teams and/or managing managers, ideally across multiple functional areas
• Excellent communication and stakeholder management skills
• Proven ability to manage multiple priorities and drive execution across teams
• Notion or similar project management platforms, reporting and business intelligence tools)