HR Director- Compliance, Legal and Benefits

HR Director- Compliance, Legal and Benefits

Harbor IT delivers a comprehensive range of IT and cybersecurity services through a streamlined one-stop-shop model. This integrated approach simplifies communication, enabling clients to coordinate with a single provider, thereby minimizing complexity and reducing breakdowns in communication.

Our key services include:

• Comprehensive IT Managed Services

By keeping these services under one umbrella, we enhance cost efficiency, ensuring significant savings compared to managing multiple vendors. Our expert team guarantees consistent service quality and reliability across all solutions, and our single-source model accelerates decision-making and implementation for quicker project completion. Serving a diverse array of client verticals, we provide tailored solutions that cater to the unique needs of each industry.

Salary Range : $100,000-$150,000 per year

Employment Type: Full-Time, Exempt

Location: Remote (U.S. Based)

About the Role: We are seeking an experienced and proactive Director of Human Resources – Compliance, Legal, and Benefits to lead and scale key HR functions that support Harbor IT’s continued growth. Reporting to the Chief Finance Officer, this role is responsible for ensuring our HR practices are compliant, legally sound, and strategically aligned with business objectives. The Director will oversee two team members and serve as a trusted advisor to senior leadership across the organization.

This is a high-impact, fully remote role ideal for a hands-on leader who thrives in a dynamic, fast-paced environment and has a strong foundation in HR compliance, employee relations, and benefits administration.

Key Responsibilities

Strategic Leadership & Team Management

• Lead the Compliance, Legal, and Benefits vertical of HR, managing and developing two direct reports.

• Act as a strategic partner to executive leadership on legal and compliance matters impacting the workforce.

• Contribute to the overall HR strategy, aligning initiatives with company goals and employee needs.

HR Compliance & Legal Oversight

• Ensure ongoing compliance with federal, state, and local employment laws (FMLA, FLSA, ADA, EEOC, etc.).

• Maintain and regularly update the employee handbook, HR policies, and procedures.

• Manage complex employee relations matters, conducting investigations and working with legal counsel as appropriate.

• Lead internal HR audits and ensure documentation and data practices meet legal standards.

Benefits Strategy & Administration

• Oversee and evaluate all employee benefits programs, including health, dental, vision, life insurance, FSA/HSA, 401(k), and paid leave.

• Lead annual open enrollment processes and manage vendor relationships.

• Analyze plan utilization and market trends to recommend cost-effective, competitive benefits offerings.

• Serve as escalation point for complex benefits issues and coordinate with providers as needed.

Policy Development & Training

• Design and implement training programs for managers and employees related to HR compliance,

• workplace ethics, and legal topics.

• Proactively interpret and apply new employment laws and regulations to existing practices.

• Provide legal and compliance guidance for organizational changes and strategic initiatives.

HR Systems, Data, & Documentation

• Oversee HRIS records and reporting to ensure data integrity, compliance, and confidentiality.

• Develop and maintain scalable systems and documentation for audits, internal controls, and reporting requirements.

Qualifications

• Bachelor’s degree in Human Resources, Business Administration, or related field; JD or master’s degree preferred.

• 7+ years of progressive HR experience, including 3+ years in a leadership or director-level role.

• Deep understanding of U.S. labor laws, HR compliance standards, and benefits administration.

• Strong analytical, organizational, and interpersonal skills.

• Demonstrated success managing direct reports and working cross-functionally with executive teams.

• HR certification (e.g., SHRM-SCP, SPHR) strongly preferred.

• Experience with Rippling preferred

What We Offer

• 100% remote work with flexible scheduling

• Fast-paced, collaborative, and mission-driven culture

• Investment in professional development and career growth

Harbor IT is an Equal Opportunity Employer. We value diversity and are committed to creating an inclusive environment for all employees.

The pay range for this role is:

100,000 - 150,000 USD per year (Remote (United States))