Director of Workforce, Safety and Compliance

Reports To: Chief Operating Officer (COO) 

Position Summary 

The Director of Workforce, Safety & Compliance is responsible for overseeing workforce administration, safety reporting, regulatory compliance, and vendor oversight for a contractor-driven telecom services organization operating in the continental United States and Puerto Rico. This role ensures Cat5 Resources LLC and Cat5 Caribbean operations maintain compliant independent contractor and vendor relationships while supporting safe, efficient, and audit-ready field operations. The position partners closely with the COO to reduce risk, meet carrier requirements, and support innovation and scalable growth across multiple jurisdictions. 

Independent Contractor & Workforce Oversight 

• Oversee the administration and integrity of the HRIS database, ensuring accurate data management and the timely, compliant execution of bi-weekly payroll across internal, seasonal, and vendor workforces.  

Oversee onboarding, documentation, and classification of independent contractors and W-2 employees across U.S. and Puerto Rico operations 

• Ensure compliance with U.S. federal, state, and Puerto Rico labor laws, including proper contractor classification under Puerto Rico Department of Labor and Human Resources (PRDOLHR) guidance 

• Maintain contractor agreements aligned with Puerto Rico civil law requirements, insurance mandates, and tax documentation 

• Ensure compliance with Puerto Rico wage, hour, and employment standards for any W-2 personnel 

• Partner with operations to ensure contractor performance, safety, and compliance expectations are met without creating employee misclassification risk 

• Administer and manage state and federal workforce compliance matters, including unemployment insurance claims and leave of absence programs, ensuring timely and accurate regulatory responses. 

Vendor & Third-Party Management 

• Oversee onboarding, compliance, and performance management of vendors, subcontractors, and third-party service providers in the U.S. and Puerto Rico 

• Ensure vendors maintain required Puerto Rico business registrations, licenses, and insurance coverage 

• Maintain vendor agreements compliant with Puerto Rico commercial and labor regulations 

• Coordinate vendor audits, reviews, and corrective action plans, including Puerto Rico-specific compliance findings 

• Track vendor performance, safety incidents, and compliance metrics across all regions 

Safety Oversight & Reporting 

• Oversee safety programs and reporting for contractor- and vendor-based field operations in the U.S. and Puerto Rico 

• Ensure compliance with OSHA standards and Puerto Rico Occupational Safety and Health Administration (PR OSHA) requirements 

• Maintain required safety logs, incident reports, and training documentation for Puerto Rico operations 

• Coordinate safety training and certification tracking specific to Puerto Rico jobsite requirements 

• Serve as primary contact for carrier safety audits, PR OSHA inspections, and compliance reviews 

Compliance & Risk Management 

• Ensure compliance with U.S. federal, state, and Puerto Rico labor, safety, tax, and contractor regulations 

• Maintain safety manuals, policies, and compliance documentation adapted for Puerto Rico legal and regulatory requirements 

• Support internal and external audits, including carrier, insurance, and Puerto Rico regulatory audits 

• Oversee investigations related to safety incidents, vendor non-compliance, or regulatory findings in Puerto Rico 

• Mitigate organizational risk through proactive cross-jurisdiction compliance monitoring 

Oversee and monitor multi-state quarterly and year-end payroll tax filings and reports for accuracy, timeliness, and compliance through Rippling and related service providers. 

Workforce Operations & Culture (Contractor-Appropriate) 

• Support a professional, safety-focused, and accountable contractor and vendor culture across all regions 

• Oversee onboarding orientation processes tailored to Puerto Rico operational requirements 

• Provide guidance to operations leaders on contractor and vendor communication boundaries within Puerto Rico labor law constraints 

• Support retention of high-performing contractors and vendors operating in Puerto Rico 

Systems, Reporting & Operations 

• Manage workforce, vendor compliance, and safety reporting systems across U.S. and Puerto Rico operations 

• Track and analyze workforce, vendor, and safety metrics to identify trends and improvement opportunities 

• Oversee third-party compliance platforms required by carriers and Puerto Rico regulators 

• Manage departmental budgets related to compliance, training, and safety 

• Provide regular reporting to the COO on workforce compliance, vendor performance, safety metrics, and Puerto Rico-specific risk exposure 

Qualifications 

• Bachelor’s degree in Business Administration, Safety Management, Human Resources, or related field 

• 7+ years of experience in workforce, safety, or compliance leadership within contractor-driven or field-based industries 

• Strong working knowledge of independent contractor regulations and vendor compliance 

• Experience supporting multi-state or territorial operations, including Puerto Rico, required 

• Knowledge of OSHA, PR OSHA, and Puerto Rico labor law requirements 

• Strong documentation, audit-management, and cross-jurisdiction compliance skills