Senior Director of Payroll Operations and Services, Restaurant365
$169.2-270.8k
+ Equity Option Grant
Restaurant management software
Open for applications
Restaurant management software
1001+ employees
Open for applications
$169.2-270.8k
+ Equity Option Grant
1001+ employees
Company mission
To help restaurants increase sales control food costs, and optimize labor.
Role
Who you are
- 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
- 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
What the job involves
- 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
- 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. This includes financial institutions as well as technology providers
- 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
Our take
Restaurant management can be rather outdated, often relying on spreadsheets and physical receipts. Restaurant365 develops all-in-one management software solutions for the restaurant industry, encompassing accounting, analytics, staff, and inventory management within its toolkit.
Restaurant365’s customer base isn’t just restaurants though, it’s software attracts accounting firms that work with restaurants as well as small eateries and large franchises. It’s expansive customer base is reflected in the amount of funding that it has received since its founding in 2011, now making it a verified Unicorn.
Restaurant365’s most recent round of funding came in 2024, and its $175 million will be invested into further enhancing its product. The company's success is unprecedented, as most would bet that restaurant industries post-pandemic would struggle to get back on their feet. Restaurant365 defied expectations though, and actually turned out to be the company that COVID-hit restaurants relied on to keep their heads above water. This goes some way to explain the success of Restaurant365, which is a proven aid for the ailing dining industry.
Kirsty
Company Specialist at Welcome to the Jungle
Insights
118% employee growth in 12 months
Company
Funding (last 2 of 5 rounds)
May 2024
$175m
GROWTH EQUITY VC
May 2023
$135m
LATE VC
Total funding: $437.5m
Company benefits
- Fully Covered Health Insurance: R365 provides comprehensive medical, dental, and vision coverage—100% paid for full-time employees.
- Flexible Time Off: Recharge when you need, so you can stay energized and focused.
- 401k with employer math.
- Stock options to purchase equity.
- Health Savings and Flexible Spending Accounts.
- Employee discount programs to lifestyle vendors and servcies.
- Annual learning and development reimbursement.
- Access to LinkedIn Learning.
- Employee recognition and TIP program.
- Fertility guidance and support.
- Online legal solutions.
- Paid parental leave.
- Disability insurance.
- Pet and life insurance.
- Wellness programs.
- Health concierge and support.
- Meditation and mindfulness courses.
- Gym discounts and virtual fitness classes.
Company HQ
East Irvine, Irvine, CA
Leadership
Tony Smith
(Co-Founder & CEO)Previously on the Board of Directors at Dynamic Methods. Before that, they were a Director of Services there.
Morgan Harris
(Co-Founder & Chief Customer Advocate)Previously Partner and Co-Founder at Dynamic Methods, Account Executive/Senior Consultant at Foreshock and Auditor at PriceWaterhouseCoopers.
John Moody
(Co-Founder, Chief Strategist & Board Member)Previously CRM Managing Partner and Board Member at Dynamic Methods.
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