Human Resources Director

The HR Director plays a critical leadership role in shaping and sustaining a high-performing, people-first culture. This individual serves as a trusted HR Business Partner to managers and employees across the organization while overseeing a small HR team. The HR Director is responsible for a full spectrum of human resources functions, overseeing a team that manages benefits and leave administration, onboarding and offboarding, and employee events, while personally driving employee relations and fostering company culture. This is a true generalist role - no two days look the same, and no task is beneath you. If you find yourself equally comfortable crafting a people strategy and tracking down a missing W-2, you'll fit right in. Success in this role requires exceptional judgment, a high degree of flexibility, and the ability to balance strategic thinking with hands‑on execution in a dynamic environment. RESPONSIBILITIES Lead, mentor, and develop a small HR team, fostering a collaborative and service-oriented department culture Set clear goals and priorities for the HR team, ensuring efficient delivery of HR services across the organization Model and promote Plymouth Rock's values and a culture of accountability and continuous improvement HR Business Partner Partner with business unit leaders as a trusted HR advisor, working alongside managers to navigate performance management, employee relations, conflict resolution, and disciplinary matters together Build strong, trusted relationships with business unit leaders to understand their goals and proactively align HR support with business needs Analyze HR metrics and trends to identify opportunities and drive proactive solutions Benefits & Leave Administration Provide oversight and direction for benefits and leave of absence programs, including FMLA, state leave, parental leave, ADA accommodations, and short- and long-term disability, ensuring compliance and consistency Guide and support the benefits function to ensure programs are administered accurately, consistently, and in compliance with applicable laws Serve as an escalation point for complex cases, providing guidance to ensure sound resolution HR Operations Manage core HR operational processes, including onboarding, offboarding, employee records, and status changes, ensuring accuracy and efficiency Streamline HR workflows and processes, identifying opportunities to reduce manual work and improve turnaround times Serve as a point of contact for employees and managers on HR policies, procedures, and general operational questions Support payroll, benefits administration, and leave management processes to ensure timely and accurate execution Provide oversight and direction for employee events and engagement activities Serve as a go‑to problem solver for the day to day HR issues that don't fit neatly into a process, jumping in wherever needed to keep things running smoothly QUALIFICATIONS Bachelor's degree required; advanced degree preferred Minimum 10 years of progressive HR experience, with demonstrated growth in scope and responsibility Prior experience managing or leading an HR team required Proven HR Business Partner experience, including coaching leaders and managing complex employee relations matters Experience in the insurance or financial services industry preferred Strong knowledge of federal and state employment law and HR compliance requirements Demonstrated ability to exercise sound judgment and handle sensitive matters with discretion and confidentiality Ability to translate HR data and analytics (turnover, engagement, headcount, compensation trends) into actionable insights and recommendations for senior leadership High degree of flexibility and adaptability; comfortable shifting priorities in a fast‑paced environment Excellent interpersonal, written, and verbal communication skills Proficiency with HRIS platforms and Microsoft Office Suite SALARY RANGE The pay range for this position is $185,000 to $235,000 annually. Actual compensation will vary based on multiple factors, including employee knowledge and experience, role scope, business needs, geographical location, and internal equity. PERKS & BENEFITS 4 weeks accrued paid time off, 8 paid national holidays per year, and 2 floating holidays Low cost and excellent coverage health insurance options that start on Day 1 (medical, dental, vision) Annual 401(k) Employer Contribution Free onsite gym and health center at our Woodbridge Location Resources to promote Professional Development (LinkedIn Learning and licensure assistance) Robust health and wellness program and fitness reimbursements Various Paid Family leave options including Paid Parental Leave Tuition Reimbursement ABOUT THE COMPANY The Plymouth Rock Company and its affiliated group of companies write and manage over $2 billion in personal and commercial auto and homeowner’s insurance throughout the Northeast and mid-Atlantic, where we have built an unparalleled reputation for service. We continuously invest in technology, our employees thrive in our empowering environment, and our customers are among the most loyal in the industry. The Plymouth Rock group of companies employs more than 1,900 people and is headquartered in Boston, Massachusetts. Plymouth Rock Assurance Corporation holds an A.M. Best rating of “A-/Excellent”. #J-18808-Ljbffr Plymouth Rock Assurance