Director of Benefits

Direct Hire Portland, Maine

• Location: Portland, Maine
• Type: Direct Hire
• Job #20415

Why You Will Love This Role

Are you a strategic benefits leader who wants to make a meaningful impact? ProSearch is representing a mission-driven nonprofit healthcare organization in Maine that is looking for a Director of Benefits to join its senior HR leadership team.
In this highly visible position, you will support a dedicated workforce who provide essential care to their communities. Your work will ensure that every member of the care team has access to high-quality, competitive benefits that reflect the organization’s values and commitment to wellness.

Highlights of the Role

• Lead the benefits function for one of Maine’s largest healthcare systems

• Join a collaborative group of peers including directors of HRIS, Compensation, Support Center, and Employee Health

• Contribute to a mission that prioritizes people and community impact over profit

• Enjoy a hybrid schedule with three days in the office and two days remote. Time in the office will be greater initially to build relationships and learn the systems

What You Will Do

As the Director of Benefits, you will:

• Develop and execute a comprehensive benefits strategy that supports organizational goals and market competitiveness

• Oversee the daily administration of all health, dental, vision, life, disability, retirement, and wellness programs

• Build and maintain strong vendor relationships, including contract negotiations and performance management

• Lead the annual benefits open enrollment process and related communications

• Ensure full compliance with federal and state regulations such as ERISA, ACA, HIPAA, COBRA, FMLA, and IRS requirements

• Research market trends, benchmark programs, and introduce innovative benefit solutions

• Partner with the Finance team on budgeting, forecasting, and cost analysis

• Mentor and develop a team of benefits professionals

• Work collaboratively with HR, Legal, Payroll, and IT to ensure accuracy and efficiency in benefits administration

• Champion wellness programs that support employee well-being, engagement, and productivity

• Serve as an escalation point for complex benefits questions and issues

What We Are Looking For

• Bachelor’s degree in Human Resources, Business Administration, or a related field. A Master’s degree or certification such as CEBS or SPHR is preferred

• At least eight years of progressive experience in benefits management, including a minimum of three years in a leadership role

• Strong understanding of benefits regulations, compliance, and best practices

• Proven success leading large-scale programs in organizations with more than 1,000 employees, ideally within a self-insured healthcare environment

• Excellent negotiation, project management, and analytical skills

• Exceptional communication and leadership abilities

• Experience using HRIS and benefits administration platforms

• A strategic mindset and genuine commitment to employee wellness and organizational mission

Who You Are

• A leader who cares deeply about people and community

• A collaborative partner who values clarity, inclusivity, and integrity

• A professional who thrives in a visible, high-impact role

• Someone who wants to help shape a benefits experience that reflects compassion and excellence

What We Offer

You will join a culture that values the people who make care possible. Benefits include:

• Generous paid parental leave

• Flexible work policy

• Student loan assistance

• Ongoing professional development and education support

• Comprehensive wellness programs for you and your family

• An inclusive environment where all voices are welcomed and respected

Ready to Make an Impact?

If you are ready to bring your expertise in employee benefits to a mission-driven healthcare organization in Portland, Maine, we would love to hear from you. Apply today and help create a benefits experience that empowers the people who care for others every day. ProSearch is proud to partner with this confidential healthcare client.

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