VP, Payroll Operations and Services

Restaurant365 is one of the fastest-growing SaaS platforms in the restaurant industry, and our payroll operations are scaling to match. We’re looking for a Vice President of Payroll Operations and Services to own the end-to-end infrastructure that keeps payroll running accurately, compliantly, and reliably for thousands of restaurant operators nationwide.

This is a high-impact, high-visibility leadership role. You’ll build and refine the operational systems, compliance frameworks, and team structures that protect our customers and enable the company to scale. You’ll work closely with Product, Finance, Legal, and Customer Success — and serve as the primary customer voice for payroll operations, ensuring our clients experience the reliability, transparency, and service quality they depend on.

If you’ve spent your career building payroll operations at scale in a SaaS environment and you’re ready to own the whole function, this role was built for you.

How you'll add value:

Operational Excellence

You’ll oversee the full delivery of payroll and financial operations — accuracy, timeliness, client satisfaction — and continuously raise the bar. That means streamlining workflows, automating wherever possible, and building KPI frameworks that keep the team accountable and ahead of issues before they become problems.

Financial Controls & Fiduciary Oversight

You’ll own everything related to payroll funds: proper segregation, secure movement, accurate funding, and daily reconciliations. You’ll ensure timely and compliant payroll tax filings across all federal, state, and local jurisdictions — including year-end reporting — and maintain the internal controls (approval workflows, audit readiness, GL alignment) that protect our clients and the company.

Compliance & Regulatory Management

You’ll be the executive point of escalation for tax authority notices, audits, and compliance matters. You’ll monitor regulatory changes across jurisdictions, update policies and procedures proactively, and develop training programs that embed compliance awareness across the organization.

Strategic Growth

You’ll partner with the executive team to shape the strategic direction of the function — identifying market trends, managing cost-to-serve, and building the organizational infrastructure needed to support a rapidly growing client base.

Client & Vendor Relationships

You’ll build trusted partnerships with our clients and with the financial institutions and technology vendors that support our operations — ensuring that every relationship is anchored in transparency, reliability, and regulatory soundness.

Team Leadership

You’ll lead, mentor, and grow a high-performing team. That includes recruiting top talent, building career paths, and creating a culture where accountability and continuous improvement aren’t just values — they’re how work gets done.

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

What Success Looks Like in Year One

• Payroll operations are running with measurably improved accuracy, speed, and compliance consistency across all client accounts
• A scalable compliance and internal controls framework is in place and audit-ready
• Key operational KPIs are defined, tracked, and trending in the right direction
• The team has a clear organizational structure with strong second-line leaders developing beneath you
• Cross-functional relationships with Product, Finance, and CS are functioning as true partnerships, with payroll operations embedded into the product roadmap process

What You’ll Bring

• 12+ years of progressive leadership in payroll and financial operations, with substantial experience in a SaaS-based payroll or payroll services organization supporting multi-entity, multi-state clients
• 5+ years of direct ownership over payroll tax compliance — federal, state, and local — including filings, remittances, wage and hour adherence, and audit response in complex, multi-jurisdiction environments
• Demonstrated ability to build and scale high-performing operations teams, including QA frameworks, compliance programs, and structured process improvement
• Strong financial management skills: payroll liabilities, funding models, reconciliation, margin performance, and cost-to-serve within a recurring revenue business
• Experience overseeing payment operations and banking relationships, including ACH processing, NACHA compliance, funding risk management, and fraud mitigation
• Hands-on familiarity with payroll platforms, tax engines, accounting systems, and treasury workflows — with enough technical fluency to be a meaningful partner to Product and Engineering
• Exceptional communication and executive presence; the ability to translate complex regulatory requirements into clear operational and client-facing strategies
• Bachelor’s degree in Finance, Accounting, Business Administration, or related field required
• MBA, CPA, CPP, or equivalent professional certification preferred
• Prior experience in banking, financial services, or regulated payment environments is a plus
• Experience supporting the hospitality or restaurant industry is a strong plus

R365 Team Member Benefits & Perks

• Comprehensive medical, dental, and vision coverage
• 401k + matching
• Equity Option Grant
• Unlimited PTO + Company holidays
• Wellness initiatives

Why join our amazing team?

We’re a product-led company that takes operations seriously. Our platform is the back-office backbone for restaurants across the country — and payroll is one of the most critical services we deliver. The team you’ll lead does work that matters to real businesses and real people every day.

We’re committed to building a culture where strong performers thrive, careers grow, and the best ideas win — regardless of where they come from.