Job Description

The Director of Operations will oversee the day-to-day operational performance of the Employee Benefits division, ensuring processes, teams, and systems are positioned to support continued growth and outstanding service delivery. This individual will focus on improving operational efficiency, creating consistency across workflows, and strengthening collaboration between internal teams, carriers, and external partners. The role requires a practical, solutions-oriented leader who can balance strategic planning with hands-on execution while supporting both client satisfaction and employee success.


Compensation: $120k - $140k
Location: Portland, ME (hybrid)

Responsibilities

• Lead operational planning and execution for the Employee Benefits division, ensuring alignment with overall business objectives.
• Establish and improve procedures across onboarding, renewals, servicing, and administrative operations to promote efficiency and consistency.
• Identify workflow bottlenecks and implement process improvements that enhance turnaround times and service quality.
• Work closely with sales, client service, and leadership teams to support retention, growth, and overall client experience.
• Monitor operational performance metrics and use data to identify trends, improve productivity, and address gaps.
• Manage relationships with carriers and third-party vendors to ensure responsiveness, accountability, and service expectations are maintained.
• Recruit, mentor, and develop operations staff by creating clear expectations and fostering a collaborative, high-performing culture.
• Support organizational and system changes by leading operational rollouts, process updates, and team communication efforts.
• Partner with internal technology teams to assess and implement tools that improve reporting, workflow management, and operational visibility.
• Maintain compliance with industry regulations, company policies, and internal quality standards.
• Develop reporting structures and operational dashboards that provide leadership with visibility into team performance and business trends.

What We're Looking For

• Experience leading operations within employee benefits, insurance, financial services, or another professional services environment.
• Track record of improving processes and building scalable operational systems.
• Strong leadership and team development experience, including coaching and performance management.
• Knowledge of employee benefits administration, renewals, carrier coordination, and client service operations.
• Strong analytical and organizational skills with the ability to manage multiple priorities effectively.
• Excellent communication and collaboration skills across departments and leadership levels.
• Ability to navigate change and drive results in a fast-moving environment.
• Relevant professional certifications (e.g., CEBS, CPCU, PMP or Lean/Six Sigma) a plus.

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