Employee Benefits Operations Lead - Remote at Digital Insurance LLC

Our Newest Opportunity:

The Employee Benefits Operations Lead serves as a strategic partner to the National Practice Leader, playing a pivotal role in driving a high-performance, growth-oriented Employee Benefits practice. The role is responsible for supporting and optimizing day-to-day operations, collaborating with Marketing, engaging with carriers and partners, and coordinating events and programs that advance key strategic initiatives. By maximizing field support, identifying efficiencies across markets, and implementing innovative solutions, this role ensures seamless execution of business processes and continuous improvement in service delivery. The Lead works cross-functionally to coordinate efforts among teams, enhance client retention, and enable cross-sale opportunities, ultimately benefiting both organizations and their employees and fostering a collaborative, results-driven environment.

Essential Duties and Responsibilities:

Growth, Retention & Cross‐Sale Enablement

• Develop and manage programs that support sales and client management teams with resources, reporting, and coordination to drive new business, renewals, and client retention.
• Track and coordinate cross‐sale initiatives with other practices (e.g., Retirement, HR Consulting, Property & Casualty), including collateral organization, meeting preparation, and follow‐up on outcomes.
• Analyze client and portfolio data to identify vulnerable clients, recommend targeted retention actions, and monitor effectiveness, surfacing insights and recommendations for leadership.

Marketing, Campaigns & Communications

• Partner with Marketing to design and execute national campaigns, manage content calendars, and develop EB‐specific messaging and materials aligned with practice strategy.
• Review and interpret engagement metrics and qualitative feedback to inform future initiatives and optimize communication strategies.

Regional & Local Market Support

• Coordinate regional initiatives, visits, and events, ensuring alignment with national standards and strategic priorities and ensuring timely follow‐up on action items.
• Serve as a connector between national leadership and local teams, facilitating best‐practice sharing and feedback loops to inform national planning.

Carrier & Partner Engagement

• Collect, analyze, and organize carrier performance data; prepare materials and recommendations for advisory meetings and track action items to completion.
• Coordinate and help shape initiatives with carrier and vendor partners to align with practice strategy and performance goals.

Training & Learning

• Oversee scheduling, logistics, and resource planning for EB training programs and field development curricula.
• Maintain and organize training resources for ongoing team reference and recommend enhancements based on participation, feedback, and evolving business needs.

Analytics & Performance Management

• Use Power BI and other tools to extract, organize, and report on key metrics (e.g., revenue, pipeline, retention, cross‐sales).
• Develop standard reporting templates and dashboards and surface insights and recommendations to leadership to inform decision‐making and performance improvement.

Product & Technology Support

• Support rollout, adoption, and optimization of EB‐specific products and technology solutions, serving as an operational point of contact for the practice.
• Coordinate user communications, training, and feedback collection, and recommend enhancements to improve utilization and user experience.

Practice Communications & Knowledge Management

• Assist with planning, content development, and execution for town halls, newsletters, and internal communications that support practice priorities.
• Maintain the Employee Benefits Practice page and related repositories to ensure resources are current, well‐organized, and easily accessible for field and leadership teams.

Event Support

• Plan and execute EB‐related events, including agenda development, content collection, speaker coordination, and logistics.
• Manage post‐event follow‐up, evaluation, and feedback; translate learnings into recommendations for future events and initiatives.

Qualifications, Skills, and Requirements

• Strong organizational and project management skills; able to manage multiple priorities and deadlines in a fast‐paced, matrixed environment.
• Demonstrated adaptability and learning agility to respond quickly to shifting needs, evolving products, and changing business goals.
• Advanced proficiency in Microsoft Office (Excel, PowerPoint); Power BI experience preferred.
• Excellent written and verbal communication skills, including preparation of executive‐ready materials and effective cross‐functional collaboration.
• Proven ability to build relationships and collaborate with Sales, Client Management, Marketing, Product/Technology, L&D, and Carrier/Vendor partners.
• High attention to detail, strong time management, and consistent follow‐through.
• Comfort working with performance metrics, reports, and analytics to inform recommendations and decisions.
• Ability to handle sensitive information with discretion and professionalism.

Education and Experience

• Bachelor’s degree preferred; professional certifications a plus.
• 5+ years’ experience in employee benefits, insurance brokerage/consulting, or a related field involving operational support, analytics, or program coordination.

City and County of San Francsico

City of Los Angeles

County of Los Angeles