Top 17 Benefit specialist Jobs in Portland Me

Director of Employee Benefits Operations
Cross Insurance —Portland, ME
- $120,000 - $140,000 a year
- Full-time
- Hybrid work
- PMP
- Office
- Finance
- Health insurance
- Dental insurance
Sales Variable Compensation Specialist
Velotic —Portland, ME
- Full-time
- Hybrid work
- Mid-level
- Finance
- Analysis skills
Quick Apply
Account Analyst, Employee Health & Benefits
Marsh McLennan Agency —Portland, ME
- Full-time
- Hybrid work
- Microsoft Excel
- Microsoft Outlook
- Office
- Health insurance
- Dental insurance
Consultant, Employee Health Benefits
Marsh McLennan Agency —Portland, ME
- Full-time
- Hybrid work
- HIPAA
- Mid-level
- Travel
- Disability insurance
- Health insurance
Payroll, Benefits, and Gifts Processing Specialist
Boys & Girls Clubs of Southern Maine —Portland, ME
- Part-time
- Research
- Mid-level
- 3 years
- Dental insurance
- 401(k)
Quick Apply
Sr Health and Benefits Sales Agent
Paychex —Portland, ME
- $55,000 a year
- Full-time
- Remote
- Background check
- Mid-level
- Continuous improvement
- Paid holidays
- Health insurance
Client Integration Specialist (Pharmacy Benefits)
Ventegra —United States
- $28 - $32 an hour
- Full-time
- Customer service
- Mid-level
- Office
- Health savings account
- Health insurance
Quick Apply
4d

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Social Security Disability Benefits Specialist
Southeast Healthcare —Columbus, OH
Valid driver's license and insurance. Minimum of AA/BA required; CWIC certification a plus. Ability to work effectively as part of an interdisciplinary team.
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Benefits Manager- Worthington, OH
Interim HealthCare —Columbus, OH
Knowledge of all pertinent federal and state regulations, filing and compliance requirements, both adopted and pending, affecting employee benefits programs,…
Quick Apply
13d

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Director of Employee Benefits Operations

Cross Insurance -
Portland, ME

Apply Now

Job Details

Full-time
$120,000 - $140,000 a year

Benefits

Health insurance
Dental insurance
Paid time off
Vision insurance
401(k) matching

Qualifications

Vendor relationship building
Bachelor's degree

Full Job Description

The Cross Family of Agencies welcomes you. We need your talent and expertise.

Director of Operations, Employee Benefits

Position Summary

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.

Key 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.

Leadership & Strategic Impact

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.

Qualifications

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.

Education

Bachelor’s degree in Business Administration, Operations Management, Finance, Insurance or a related field required.
Master’s degree (MBA or similar) preferred.
Relevant professional certifications (e.g., CEBS, CPCU, PMP or Lean/Six Sigma) a plus.

Why Cross Insurance

At Cross Insurance, we are committed to building strong teams, developing leaders, and delivering exceptional service to our clients. The Director of Operations plays a critical role in shaping the future of our Employee Benefits Division and making a meaningful impact across the organization.

Compensation: The base salary range for this role is $120,000–$140,000 annually. Actual compensation will be based on factors including location, skills, experience, and internal equity. Cross Insurance offers a comprehensive benefits package including medical, dental, vision, 401(k) with match, paid time off, and more

Apply Now

Refine Your Search

benefit specialist jobs in portland me

Director of Employee Benefits Operations

Sales Variable Compensation Specialist

Account Analyst, Employee Health & Benefits

Consultant, Employee Health Benefits

Payroll, Benefits, and Gifts Processing Specialist

Sr Health and Benefits Sales Agent

Client Integration Specialist (Pharmacy Benefits)

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Director of Operations, Employee Benefits

Position Summary

Key Responsibilities

Leadership & Strategic Impact

Qualifications

Why Cross Insurance

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