Senior Director, Payroll Operations and Services

Job Description: • Oversee the delivery of payroll and financial operations, including payments, to ensure accuracy, timeliness, and client satisfaction. • Streamline processes to improve efficiency and service quality. • Leverage technology and automation to scale operations and enhance customer experiences. • Monitor and optimize KPIs to achieve and exceed operational goals. • Own fiduciary oversight of all payroll funds, ensuring proper segregation, secure movement, accurate funding, and daily reconciliations to protect client and company assets. • Ensure timely and compliant payroll tax filings and remittances across all federal, state, and local jurisdictions, including year-end reporting and regulatory documentation. • Establish and maintain strong internal controls, including segregation of duties, approval workflows, and reconciliation processes to safeguard financial integrity. • Oversee payroll-related financial reporting, ensuring accurate general ledger alignment, liability tracking, accrual validation, and audit readiness. • Lead regulatory response and issue resolution, serving as the executive escalation point for tax authority notices, compliance matters, and financial discrepancies. • Implement risk mitigation frameworks to prevent funding errors, compliance failures, and financial exposure, while ensuring operational scalability and audit compliance. • Ensure full compliance with federal, state, and local regulations related to payroll, tax, and financial transactions, including IRS and Department of Labor requirements. • Lead internal and external audits, assessing and mitigating risks to maintain operational integrity. • Stay updated on regulatory changes and adjust policies and procedures accordingly. • Act as the primary liaison for audits and regulatory reviews. • Develop and deliver training programs to promote compliance awareness across the organization. • Collaborate with the executive team to define and execute strategic initiatives aligned with company objectives. • Identify market trends to enhance service offerings and expand the client base. • Drive initiatives focused on cost management, scalability, and profitability. • Build and maintain strong client relationships, ensuring transparency and compliance in service delivery. • Establish and manage vendor partnerships to enhance operational efficiency and meet regulatory standards. • Lead and mentor a high-performing team, fostering a culture of accountability and continuous improvement. • Recruit, train, and develop talent to meet current and future business needs. • Promote collaboration across departments to drive innovation and operational excellence. Requirements: • 12+ years of progressive leadership experience in Payroll and Financial Operations, with significant experience in a SaaS-based Payroll or Payroll Services organization supporting multi-entity, multi-state clients. • 5+ years of experience with federal, state, and local payroll tax regulations; directly overseeing regulatory compliance, tax filings, remittances, wage and hour adherence, and audit response in complex, multi-jurisdiction environments. • Proven experience operating in a SaaS delivery model, including managing SLAs, supporting enterprise-level customers, partnering with Product and Engineering teams, and leveraging technology platforms to drive automation, reporting accuracy, and operational efficiency. • Demonstrated success leading high-performing payroll operations teams, including audit management, compliance programs, quality assurance frameworks, and structured process improvement initiatives that reduce risk and improve service consistency. • Strong operational acumen with a track record of building scalable processes, implementing workflow automation, and leveraging systems to improve accuracy, reduce manual intervention, and support high-growth customer environments. • Advanced analytical and financial management skills, with the ability to oversee payroll liabilities, funding models, reconciliation processes, margin performance, and cost-to-serve analysis within a recurring revenue business model. • Experience overseeing payment operations and banking relationships, including ACH processing, NACHA compliance, funding risk management, fraud mitigation, and vendor oversight in regulated financial environments. • Exceptional communication and executive presence, with the ability to translate complex payroll and regulatory requirements into clear operational strategies and client-facing guidance. • Proven ability to build trusted partnerships with Finance, Legal, Product, Sales, Customer Success, and executive stakeholders. • Demonstrated ability to scale operations in high-growth SaaS organizations, including building organizational structures, hiring and developing talent, and implementing KPI frameworks. • Hands-on familiarity with payroll platforms, tax engines, accounting systems, treasury workflows, and vendor payment technologies, with an understanding of integration architecture and data integrity considerations in cloud-based systems. • Bachelor’s degree in Finance, Accounting, Business Administration, or related field required; MBA, CPA, CPP, or similar professional certification preferred. • Prior experience in banking, financial services, or regulated payment environments preferred. • Experience supporting the hospitality industry is a strong plus. Benefits: • Competitive compensation package • Ability to work remote • Comprehensive medical benefits • 401k + matching • Equity Option Grant • Unlimited PTO + Company holidays • Wellness initiatives Apply tot his job Apply To this Job