Director of Compensation & Benefits

Heart Land, LLC is seeking a pragmatic, operationally minded, and highly analytical Compensation and Benefits Director to lead the design, governance, and day-to-day execution of compensation and benefits programs across a rapidly growing portfolio of operating companies.

This is a player-coach role. The Director will execute high-complexity incentive compensation modeling, analysis, program administration, and cycle management while also leading and developing one direct report (Employee & Benefits Specialist) to ensure benefits administration, compliance, and employee experience are consistently strong.

The primary focus of this role is incentive compensation program administration and ongoing improvement
: ensuring plans are clearly documented and distributed, operationally aligned, scalable, and executed with precision. As Heart Land continues to scale through organic growth and M&A, this role will serve as a trusted partner to executives, Operating Company leaders, Finance, and the unified HR team—balancing “People First. Purpose Second. Details Always.” with sound financial stewardship.

This position reports to the Vice President of Human Resources, Safety & Risk. This position has one direct report:
Employee & Benefits Specialist.

• Own the end-to-end administration and continuous improvement of Heart Land’s incentive programs, including (as applicable):
  • Operations Management Incentive Program (including specialty plans)
  • Heart Land Incentive Program
  • Account Manager Enhancement Sales Incentive Program
  • Business Development Commission programs
  • Merit increase program administration (process governance and analytics support
  • Mergers & Acquisitions specific programs:
    Build and maintain straightforward and scalable program documentation, templates, payout files, and communications.
• Ensure programs drive the right behaviors, align with operational realities, and produce predictable financial outcomes.
• Establish a disciplined annual calendar for plan refresh, publication, measurement, and payout.
• Work closely with internal teams to obtain, validate, and operationalize performance metrics that support efficient, accurate, and repeatable incentive calculations.

• Conduct modeling and scenario analysis tied to incentive design changes, performance outcomes, and payout forecasting.
• Partner with Finance and Business Intelligence to improve data visibility and reliability (dashboards, scorecards, payout readiness tracking).
• As necessary, partner with the leadership team to develop new compensation programs for roles or operations to drive the desired outcomes while maintaining practical administrative considerations.

• Maintain market wage insights for critical roles and support leadership with data-driven guidance when outliers, compression, or competitiveness concerns arise.
• Support survey participation and market pricing activities as needed; keep the approach pragmatic and scaled to current business priorities.
• Partner with HR leaders during job changes/new roles to ensure pay programs and job documentation align.
• Develop tools to enable HR Operations to efficiently run current market analyses on roles to support and enhance the “centrally guided” compensation philosophy.

• Provide leadership and oversight of benefits administration through the Employee & Benefits Specialist, ensuring strong execution across:
  • Annual renewal and open enrollment
  • Vendor coordination and issue resolution
  • Eligibility/data integrity within HRIS and carrier feeds
  • Employee advocacy, communications, and education
  • Cost containment opportunities
• Work with the unified Human Resources team to refine and adjust employee benefit offerings that are competitive, valued, and meet the needs of the employees.
• Ensure benefits-related compliance requirements are met (e.g., ACA reporting, 5500 support, audit readiness), partnering with internal stakeholders and vendors/brokers.

• Support due diligence…