Director of Compensation & Benefits

Position Overview
HeartLand, 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 HeartLand 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.
Reporting
This position reports to the Vice President of Human Resources, Safety & Risk. This position has one direct report: Employee & Benefits Specialist.
Key Responsibilities

Incentive Compensation Program Execution and Governance
Own the end-to-end administration and continuous improvement of HeartLand’s incentive programs, including (as applicable):
Operations Management Incentive Program (including specialty plans)
HeartLand 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.
Compensation Analytics, Modeling, and Decision Support
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.
Market Pricing and Practical Wage Governance
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.
Benefits Strategy Enablement and Compliance Oversight
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.
M&A Integration Support
Support due diligence and integration planning for compensation and benefits during acquisitions.
Review acquired company incentive and pay practices; recommend integration approach, timing, transition mechanics, and communication considerations.
Help operating leaders and HR partners navigate change with clarity and respect for local nuance. Key Performance Indicators

Incentive Execution: Accurate, on-time payouts and clean reconciliations; minimal rework and escalations.
Plan Readiness: On-time publication of incentive plans and supporting materials for upcoming seasons/years.
Scalable Tools: Simple, reliable templates and models that OpCos can follow consistently.
Data Quality: High-integrity inputs/outputs; documented assumptions; strong audit trail.
Benefits Operations: Smooth open enrollment, timely issue resolution, compliant reporting support, improved employee clarity and utilization.
OKR and SMART Goal Achievement: Annual progress toward goals aligned with the VP of HR, Risk & Safety.
Required
Qualifications (Skillset)

Bachelor’s degree in Business, Finance, HR, or related field.
8+ years progressive experience in compensation, incentives, finance/analytics, or closely related work; multi-site/field-based experience strongly preferred.
Demonstrated expertise in incentive compensation administration, modeling, and payout governance in field-based environments.
Strong operational and financial acumen with advanced Excel and modeling capability.
Experience partnering with executive and operational leaders; able to simplify complex data into clear decisions.
Experience in high-growth and/or private equity–backed environments.
Working knowledge of compensation/HRIS tools and market benchmarking resources.
High discretion and strong judgment with sensitive employee and company information.
Preferred

CCP or similar credential.
Experience with M&A integration of incentive and benefits programs.
Experience improving benefits financial performance through vendor optimization.
Leadership Attributes (Mindset)

Operationally Grounded: Understands field realities and designs programs leaders can execute cleanly.
Analytical and Accurate: Strong attention to detail; disciplined about data integrity and documentation.
Relentless Process Improver: Has a genuine passion for process improvement, including evaluating workflows, eliminating friction, and resourcefully using technology, automation, and custom-built tools to improve efficiency and reliability.
Player-Coach: Executes critical work personally while developing others and building sustainable processes.
Pragmatic Influencer: Knows when to push, when to coach, when to escalate, and how to earn alignment without creating noise.
Values-Driven: Models HeartLand’s values—Human, Exceptional, Accountable, Respectful, Trusted—especially when decisions are hard.
Other Requirements

Based at Kansas City HQ with hybrid flexibility; majority in-office expected.
Minimal travel (approximately 10–15%), primarily to Operating Companies and select professional development opportunities.
Maintains confidentiality and earns trust across a diverse organization.
Why Join HeartLand
Role
HeartLand is a fast-growing commercial landscape organization—built through strong local brands and cultures, guided by shared principles, and committed to delivering the ordinary in extraordinary ways. In this role, you will:

Own programs that directly impact thousands of employees across a growing national footprint.
Build disciplined, scalable incentive and benefits operations that strengthen performance and trust.
Partner closely with executives and operators to create clarity, consistency, and results.
Help shape the next phase of HeartLand’s growth with a “people-first” approach and strong financial stewardship.
This is more than a job. It’s a chance to leave your mark on a thriving company redefining how great people power great businesses.