Director of Employee Benefits Operations

Cross Insurance•Portland, ME

14h•$120,000 - $140,000

About The Position

The Director of Operations will build, lead, and optimize the operational foundation of the Cross Insurance Employee Benefits Division. This role is responsible for developing scalable processes, streamlining workflows, strengthening carrier and vendor partnerships, and driving operational excellence across all facets of the employee benefits business. The ideal candidate is a hands-on leader who translates strategy into execution, improves efficiency, and enables growth while delivering an exceptional client and employee experience.

Requirements

Proven experience leading operations within insurance, employee benefits, or a professional services environment.
Demonstrated ability to build and scale processes in a growing or complex organization.
Strong leadership skills with a history of developing, motivating, and retaining high-performing teams.
Deep understanding of employee benefits operations, including renewals, carrier relationships, and service delivery models.
Analytical mindset with the ability to evaluate data, identify trends, and implement improvements.
Excellent communication and collaboration skills across multiple functions and leadership levels.
Comfortable driving change, managing competing priorities, and delivering results in a fast-paced environment.
Bachelor’s degree in Business Administration, Operations Management, Finance, Insurance or a related field required.

Nice To Haves

Master’s degree (MBA or similar) preferred.
Relevant professional certifications (e.g., CEBS, CPCU, PMP or Lean/Six Sigma) a plus.

Responsibilities

Build and lead the operational strategy for the Employee Benefits Division, aligning people, processes, and technology with business goals.
Develop, implement, and refine standardized workflows that improve efficiency, accuracy, and scalability across new business, renewals, and ongoing service.
Streamline operational processes to reduce friction, enhance turnaround times, and ensure consistent service delivery.
Partner closely with sales, account management, and leadership to support growth initiatives and optimize client lifecycle management.
Drive continuous improvement by analyzing performance metrics, identifying gaps, and implementing solutions that elevate productivity and quality.
Oversee carrier and vendor operations, strengthening relationships, improving issue resolution, and ensuring service-level expectations are met.
Build, mentor, and develop high-performing operations teams through clear expectations, coaching, and accountability.
Lead change initiatives, guiding teams through process improvements, system enhancements, and organizational growth.
Collaborate with IT and leadership to evaluate, select, and implement operational tools and systems that enhance efficiency and reporting.
Ensure compliance with regulatory requirements and internal standards while maintaining best-in-class operational controls.
Create transparency and accountability through reporting, dashboards, and operational KPIs that inform leadership decisions.
Translate vision into action by turning strategic objectives into executable operational plans.
Act as a strategic advisor to divisional and executive leadership on operational capabilities, risks, and opportunities.
Build a culture of ownership and excellence, reinforcing Cross Insurance’s values and commitment to clients and teammates.
Anticipate growth needs and proactively design operational infrastructure that supports long-term success.