Senior Director, Payroll Operations and Services

How you'll add value:

• RESPONSIBILITIES
• Operational Leadership
• 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.
• Financial Oversight
• 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.
• Compliance and Regulatory Management
• 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.
• Strategic Planning and Growth
• 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.
• Client and Vendor Management
• 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. This includes financial institutions as well as technology providers.
• Team Development
• 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.

What you'll need to be successful in this role:

• QUALIFICATIONS
• 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. Demonstrated ownership of end-to-end payroll operations, including funding, tax compliance, reconciliations, and service delivery at scale.
• 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.

R365 Team Member Benefits & Perks

• Competitive compensation package
• Ability to work remote
• Comprehensive medical benefits
• 401k + matching
• Equity Option Grant
• Unlimited PTO + Company holidays
• Wellness initiatives

Why join our amazing team?

• We're a community that prides itself in creating innovative solutions and producing quality work
• Our product is the secret ingredient that makes a real difference to restaurants nationwide
• The open concept work environment that we've created is causal, collaborative, and cultivates communication
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