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Senior Manager, Total Rewards

Reports to: VP of Talent Status: Full-Time, Exempt Location: Remote

Who We Are:

We are a private-equity-backed, multi-brand operating platform in the vacation rental and hospitality services space. We partner with founder-led and operator-driven businesses across the U.S. to help them scale while preserving what makes them great locally.

The Opportunity:

We are seeking a Director of Total Rewards to design and lead our compensation, benefits, and rewards strategy. This is a foundational role reporting to the VP of Talent and working closely with the executive team to build the programs that enable our people strategy and support long-term value creation.

Approximately 50% of this role is focused on compensation design and administration — establishing market-aligned pay bands, supporting our Management Incentive Plan (MIP), and building the analytical foundation for enterprise-wide pay decisions. The balance of the role spans benefits strategy and administration, bonus program oversight, and talent analytics that inform people planning and investment decisions.

This is not a maintenance role. You will build programs from the ground up, introduce structure where there is ambiguity, and operate as a true strategic partner to HR and the business. If you thrive on building in a high-growth, PE-backed environment and are energized by using data to drive decisions, this is your opportunity.

What You’ll Do

Compensation Design & Administration

• Design and implement a comprehensive compensation architecture, including market-aligned salary bands across all job families and levels
• Lead and manage annual compensation review cycles, including merit increases, market adjustments, and off-cycle equity or pay actions
• Conduct ongoing benchmarking using external surveys (e.g., Radford, Mercer, Willis Towers Watson) to ensure competitiveness across roles in distributed operations and field-based environments
• Partner with the VP of Talent and executive leadership to develop compensation strategy that supports talent attraction, retention, and internal equity
• Build and maintain job architecture frameworks, leveling guides, and FLSA classification standards across the organization
• Advise hiring managers and HR business partners on offer construction, internal equity considerations, and pay positioning

Incentive Programs & Total Compensation

• Oversee strategy and administration for the Management Incentive Plan (MIP), including plan design, eligibility, communication, and payout processing in coordination with Finance
• Design and administer short-term incentive (STI) programs, including quarterly and annual bonus structures tied to individual and company performance metrics
• Support development and communication of long-term incentive (LTI) programs in partnership with PE sponsors and executive leadership
• Ensure total compensation packages are competitive, internally equitable, and aligned with our performance culture and ownership mentality
• Build total compensation statements and tools that help employees and leaders understand the full value of their rewards

Benefits Strategy & Administration

• Lead benefits strategy, vendor selection, and program design, including medical, dental, vision, life and disability insurance, and 401(k), with a focus on value, cost efficiency, and employee experience
• Manage the annual open enrollment process end-to-end, including communication planning, carrier coordination, and system configuration
• Evaluate and optimize leave programs (FMLA, parental leave, PTO) to ensure compliance and market alignment
• Oversee benefits administration systems and partner with HR Operations to ensure accurate, timely processing
• Monitor benefits spend and utilization trends; develop recommendations for plan changes during renewal cycles
• Ensure compliance with federal, state, and local benefits regulations (ACA, ERISA, COBRA, HIPAA) across a multi-state workforce

Talent Analytics & People Insights

• Build and maintain people analytics capabilities that provide the organization with actionable insights on compensation equity, retention risk, workforce planning, and talent ROI
• Develop executive and board-ready reporting on total rewards spend, compensation competitiveness, benefits utilization, and headcount trends
• Partner with Finance and FP&A on headcount planning, labor cost modeling, and compensation forecasting
• Design and analyze employee surveys, pay equity audits, and workforce segmentation to surface insights that inform strategy
• Support M&A diligence and integration by assessing acquired company compensation structures, benefits plans, and total rewards gaps

What You’ll Bring

Education & Experience

• 8+ years of progressive total rewards experience, with demonstrated depth in both compensation design and benefits program management
• Experience building or significantly redesigning compensation structures, including job architecture, pay band development, and incentive plan design
• Background in distributed services, multi-site operations, field-based business models, or PE-backed environments strongly preferred (e.g., hospitality, property management, facilities services, retail operations)
• Track record of owning total rewards outcomes end-to-end in a lean or high-growth environment, rather than as part of a large, siloed HR function
• Experience supporting executive compensation, MIP, or LTI programs in partnership with Finance and PE sponsors is a significant plus
• CCP (Certified Compensation Professional) or CBP (Certified Benefits Professional) designation preferred; equivalent experience considered
• Bachelor’s degree required; advanced degree in HR, Business, Finance, or a related field preferred

Functional Skills

• Expert-level proficiency in compensation benchmarking methodologies and survey platforms (Radford, Mercer, WTW, or equivalent)
• Strong command of HRIS and compensation management systems (e.g., Workday, ADP, Paycom, UKG); experience with talent management platforms (CultureAmp, Leapsome, 15Five) is a plus
• Advanced analytical skills with high proficiency in Excel for modeling, scenario planning, and compensation analysis; experience with BI tools (e.g., Tableau, Power BI, Domo) preferred
• Demonstrated ability to design and administer incentive programs, including STI, LTI, and management incentive plans tied to business performance
• Deep working knowledge of benefits compliance requirements across a multi-state workforce (ACA, ERISA, COBRA, HIPAA, state-specific mandates)
• Ability to translate complex compensation and benefits data into clear, concise narratives for executive and board-level audiences

Soft Skills & Attributes

• Builder mentality — energized by creating structure and systems where none exist, not by maintaining the status quo
• Ownership mentality — you take accountability for outcomes, anticipate problems before they surface, and drive decisions with confidence
• Exceptional analytical rigor balanced with business judgment — you let data lead without losing sight of the human and business context
• Strong executive presence and communication skills — able to partner credibly with senior leaders and PE sponsors on sensitive compensation matters
• Collaborative and cross-functional — comfortable operating at the intersection of Talent, Finance, Legal, and Operations
• Discretion and integrity — total rewards involves highly sensitive information; candidates must demonstrate exemplary judgment and confidentiality
• Alignment with our core values: Servant Leadership, Ownership Mentality, Local, and Excellence

Benefits

• Comprehensive benefits package including medical, dental, vision, and 401(k)
• Remote-flexible work arrangement with travel as needed