Position Description – Payroll Senior Manager

Stakeholders VR is a first-of-its-kind alliance of best-in-class vacation rental property management companies, united by a shared vision: to redefine hospitality, drive innovation, deliver magical guest experiences, and unlock premium value through strategic collaboration and shared ownership. We’re building a movement of local operators who believe that exceptional guest & owner experiences and community-driven service can scale nationally.

𝗪𝗛𝗔𝗧 𝗪𝗘 𝗗𝗢 We bring together the top-performing PMCs in the country, hand-selected for their operational excellence, integrity, and local market leadership, and empower them through shared ownership, best-in-class technology, operational support, and group-level advantages in marketing and purchasing. Together, we’re raising the standard of vacation rental hospitality and delivering amazing experiences for our guests and homeowners.

𝗢𝗨𝗥 𝗠𝗜𝗦𝗦𝗜𝗢𝗡 To empower the best local operators by giving them the resources, reach, and capital to thrive in a competitive landscape. We believe that true hospitality and local excellence are superpowers in the right hands. Stakeholders VR exists to make sure those hands stay in control, yet go further, and faster, together.

We believe the future of travel belongs to the bold, the united, and the hospitality-obsessed.

The Role

We are seeking an experienced and strategic Payroll leader to lead the consolidated payroll function across our multi-entity platform. This role will be instrumental in establishing and maintaining robust payroll operations, standardizing processes across our portfolio companies, and providing exceptional client service to our employees across the company. The ideal candidate thrives in a complex, fast-paced environment and has proven experience implementing and maintaining payroll operations in a multi-entity or roll-up environment.

This position will require significant interaction with the entire organization. The ideal candidate is someone who brings instant credibility because of his or her accomplishments. He/she must be able to address technical and business questions and have the interpersonal skills to guide employees throughout the entire payroll cycle.

Key Competencies

  • Oversee end-to-end payroll processing operations across all initial 20+ entities plus any subsequent acquisitions, ensuring accurate and timely payroll execution, including oversight of time-tracking
  • Lead the implementation of ADP and collaborate as part of the implementation of Workday including the transition of employees from legacy payroll and HRIS systems
  • Administer payroll systems and upgrades, including testing, configuration, and process documentation
  • Manage payroll operations in compliance with federal, state, and local tax laws, wage and hour regulations, and company policies
  • Partner with the company’s HR function to ensure seamless integration and processing of all employee status changes
  • Oversee payroll tax filings, audits, and year-end activities (W-2s, 1099s, etc.), serving as the primary point of contact for auditors
  • Partner with accounting and finance leadership to streamline the general ledger reporting needs for all payroll-related activities
  • Develop and maintain payroll policies, procedures, and internal controls to ensure data integrity and compliance
  • Respond to employee payroll inquiries with a high level of confidentiality, accuracy, and customer service
  • Partner with FP&A to provide historical analysis and support forecasting and budgeting processes
  • Support integration planning and execution for new acquisitions
  • Build, lead, and mentor a high-performing payroll team potentially across multiple locations
  • Develop talent and create clear career paths for team members
  • Foster a culture of continuous improvement, accountability, and collaboration

The Successful Applicant

  • 10+ years of progressive payroll experience with at least 3 years in a manager-level role or above
  • Extensive proficiency with the ADP payroll platform, required
  • Extensive experience managing multiple pay groups and pay cycles, including full-time, part-time, and seasonal employees
  • Strong knowledge of federal, state, and local payroll tax laws, wage and hour regulations, and compliance requirements 
  • Bachelor’s degree in Accounting, Finance, Human Resources, Business Administration, or a related field (or equivalent experience)
  • Strong knowledge of federal, state, and local payroll tax laws, wage and hour regulations, and compliance requirements 
  • Experience in a multi-entity, roll-up, or private equity-backed environment in the hospitality industry, a plus
  • Experience leading payroll system implementations, upgrades, or process automation initiatives
  • Experience with HRIS platforms, preferably Workday
  • Proven ability to reconcile payroll, taxes, and general ledger accounts accurately and on deadline
  • Knowledge of benefits administration, timekeeping systems, and payroll accounting
  • High level of discretion and ability to handle sensitive and confidential information
  • Strong analytical, problem-solving, and organizational skills with exceptional attention to detail
  • Strong leadership and team management capabilities 
  • Excellent communication skills with ability to present at company-wide meetings or forums
  • Ability to manage multiple deadlines in a fast-paced environment
  • Customer-service mindset when supporting employees and stakeholders.

Location

Remote

Email careers@stakeholdersvr.com with the role of interest, a brief introduction, and your background.

Stakeholders VR. is proud to be an affirmative action / equal opportunity employer. All qualified applicants will receive consideration without regard to race, creed, gender, marital status, sexual orientation, citizenship status, color, religion, national origin, age, disability, veteran status, or any other status protected under local, state, or federal laws.