Senior Director, Payroll Operations and Services

Restaurant365 is a SaaS company disrupting the restaurant industry! Our cloud-based platform provides a unique, centralized solution for accounting and back-office operations for restaurants. Restaurant365’s culture is focused on empowering team members to produce top-notch results while elevating their skills. We’re constantly evolving and improving to make sure we are and always will be “Best in Class” ... and we want that for you too!

The Senior Director of Customer Payroll & Financial Operations is a strategic and operational leader responsible for overseeing the end-to-end execution, compliance, and scalability of customer payroll and related financial operations. This role ensures operational excellence across payroll services, regulatory compliance, financial controls, and service delivery performance.

The Senior Director will lead the cross-functional payroll and financial operations teams, establish scalable processes to support growth, and ensure strict adherence to federal, state, and local regulatory requirements. This leader plays a critical role in keeping the company and its customers from compliance risk while driving operational efficiency and customer service quality.

This position requires deep expertise in payroll, payroll compliance, financial management, process optimization, team leadership, and the ability to partner effectively with Product, Sales, Customer Success, Legal, and Finance.

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

#BI-Remote

DYN365, Inc d/b/a Restaurant365 is an equal opportunity employer.