Head of People in Tamarac, Florida at Prestige International Insurance Gr Inc

Position Summary:

Prestige Trucking Insurance is seeking a seasoned Head of People to lead its human resource functions across the organization. The Head of People is responsible for overseeing all HR functions to ensure timely, accurate, and compliant reporting. This role manages the human resources team responsible for the employees/contractor’s life cycle from end to end and is also responsible for implementing strong processes and building a good culture. The Head of People works closely with operations, finance, and external vendors to optimize the employee experience and HR processes. The ideal candidate will bring a blend of technical expertise, operational leadership, and a proactive mindset.

Essential Duties and Responsibilities:

• Develop and oversee the Human Resources Department, including setting structure, goals, and performance standards.

• Ensure compliance with all federal, state, and local labor laws and regulations.

• Lead and manage the entire spectrum of HR functions including recruitment, onboarding, performance management, compensation and benefits, team member relations, and employee development.

• Build, train, and mentor a team of Human Resources Professionals.

• Proactively evaluate HR workflows and drive improvements to enhance quality, efficiency, and scalability.

• Design and implement HR solutions tailored to evolving business needs and the company’s long-term vision.

• Support leaders in building a strong culture through consistent HR practices and team member experience initiatives.

• Partner with other leaders on strategic initiatives to ensure our people are always our focus.

• Drive key talent management initiatives including retention, acquisition, compensation, and succession planning to ensure the organization is positioned for continued growth.

• Manage relationships with vendors and consultants to ensure a competitive benefits package is available.

Knowledge, Skills, and Abilities (KSA’s):

• Strategic & Operational Leadership Skills — Demonstrates the ability to develop and oversee the HR department, set organizational structure and goals, and lead with a clear, forward-thinking approach that supports both day-to-day operations and long-term business growth.

• Business & Financial Acumen Knowledge — Possesses a strong understanding of business operations, financial principles, and organizational dynamics, enabling effective collaboration with operations and finance teams and sound decision-making in support of company objectives.

• Analytical & Problem-Solving Skills — Able to evaluate complex HR data, identify trends, assess workforce challenges, and develop practical, data-informed solutions that drive continuous improvement and organizational performance.

• Cross-Functional Team Management Abilities — Skilled in managing and partnering with teams across multiple departments and functions, fostering alignment, collaboration, and shared accountability toward common organizational goals.

• Integrity & Accountability — Consistently demonstrates a high level of professional integrity, ethical conduct, and personal accountability in all HR decisions, employee interactions, and leadership responsibilities.

• Confidentiality Knowledge & Practice — Maintains the highest degree of confidentiality when handling sensitive employee information, organizational matters, classification decisions, and executive-level communications, in full compliance with applicable laws and company standards.

• Organizational & Time Management Skills — Capable of managing multiple HR functions, priorities, and deadlines simultaneously while maintaining accuracy, efficiency, and attention to detail across all areas of responsibility.

Minimum Qualifications:

• 7–10 years of progressive human resources experience (preferably in insurance).

• Minimum 3 years of experience as a human resources manager and in leading a team.

• In-depth understanding of employee vs. 1099 classification, rules/regulations, and GAAP requirements.

• Strong leadership, mentoring, and organizational skills.

• Proven track record in change management and driving improvement initiatives.

• Experience in a high-growth environment with team members spread globally.

• Bachelor’s Degree in Human Resources or a Related Field.

Preferred:

• SHRM designation.

• Master’s Degree in Human Resources or a Related Field.

• Familiarity with ADP Workforce.

• Familiarity with accounting systems (QuickBooks, Sage, Salesforce, or similar).

Physical Demands and Work Environment:

• Requires extended periods of sitting, computer use, and handling digital documents, along with clear communication via phone and video.

• Professional office work setting with standard office equipment and moderate noise levels.

• Fast-paced environment with frequent collaboration across departments and occasional extended hours during audits, month/quarterly/year-end, or operational rollouts.

• Requires handling confidential employee and organizational information in compliance with privacy and security standards.

• Limited travel may be required for vendor, regulatory, or leadership meetings.