Cross Insurance · 4 hours ago
Employee Benefits Sales Executive
Provider - RI
Full-time
Hybrid
Senior Level
5+ years expCross Insurance is seeking an Employee Benefits Sales Executive to drive new business growth and expand client relationships through the consultative sale of employee benefits solutions. The role involves identifying opportunities, managing client relationships, and collaborating with internal teams to deliver effective benefit strategies.
Auto InsuranceFinancial ServicesInsuranceInsurTechLife Insurance
Responsibilities
Identify, prospect, and develop new employee benefits opportunities within targeted market segments
Build and maintain a robust sales pipeline through proactive outreach, referrals, centers of influence, and strategic networking
Conduct discovery meetings to understand employer objectives, workforce demographics, financial constraints, and risk tolerance
Lead the full sales lifecycle, including prospecting, needs analysis, proposal development, presentations, negotiations, and close
Position a broad range of benefit solutions, including fully insured, level-funded, self-funded, and alternative funding arrangements, where appropriate
Serve as the primary client relationship manager for sold accounts, coordinating with internal service and account management teams
Provide strategic guidance on plan design, funding strategy, contribution modeling, and long-term cost management
Participate in client meetings, renewal strategy sessions, and ongoing stewardship reviews
Maintain strong, long-term relationships with decision-makers and key stakeholders
Develop and maintain strong relationships with insurance carriers, TPAs, PBMs, and vendor partners
Stay current on carrier products, underwriting approaches, market trends, and regulatory changes affecting employee benefits
Collaborate with carrier partners to structure competitive and compliant solutions for clients and prospects
Work closely with account management, analytics, compliance, and risk teams to ensure accurate, timely, and high-quality deliverables
Ensure proper handoff of sold business to service teams, including clear documentation of plan structure, client expectations, and deliverables
Accurately document sales activity, opportunities, and forecasts within the agency’s CRM system
Meet or exceed annual new business revenue goals and defined activity metrics
Maintain a consistent pipeline that supports long-term growth objectives
Achieve high client retention and satisfaction levels through consultative selling and strong internal coordination
Demonstrate adherence to agency processes, compliance standards, and ethical sales practices
Qualification
Required
Minimum of 5 years of direct or related experience in employee benefits sales, insurance brokerage, consulting, or a similar advisory role
Strong working knowledge of group health insurance, ancillary benefits, and employer-sponsored benefit programs
Proven track record of developing new business and managing complex sales cycles
Excellent communication, presentation, and negotiation skills
Ability to explain technical benefit concepts to both executive and employee audiences
Proficiency with CRM systems, Microsoft Office, and proposal tools
Active state insurance license (or ability to obtain within a defined timeframe)
Preferred
Experience selling to mid-size or large employers
Familiarity with alternative funding strategies, cost-containment programs, and population health concepts
Existing professional network within the business or benefits community
Benefits
Comprehensive benefits package including medical, dental, vision, retirement plan, and paid time off.
Professional development and continuing education support.
Company
Cross Insurance
Cross Agency is an insurance agency that offers auto, home, renters insurance, and commercial insurance for businesses.
501-1000 employees
Funding
Current Stage
Late StageLeadership Team
Bruce Nickerson
Chief Financial Officer
James Jones
Chief Data Analytics Officer
Recent News
2025-06-30
2025-05-07
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