Employee Benefits Sales Executive

Cross Insurance

3d

About The Position

The Cross Family of Agencies welcomes you. We need your talent and expertise. Employee Benefits Sales Executive Position Summary The Employee Benefits Sales Executive is responsible for driving new business growth and expanding client relationships through the consultative sale of employee benefits solutions. This role requires a minimum of five (5) years of direct or related experience in employee benefits, insurance brokerage, or a closely aligned advisory or sales function. The ideal candidate combines strong technical knowledge of employee benefits with proven business-development expertise and a client-first mindset. The Sales Executive serves as a trusted advisor to employers, helping them navigate complex benefit decisions while delivering cost-effective, compliant, and sustainable benefit strategies.

Requirements

• 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).

Nice To Haves

• 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.
• Consultative selling and strategic thinking
• Financial and analytical acumen
• Relationship-building and influence
• Accountability and results orientation
• Collaboration and teamwork

Responsibilities

• Business Development & Sales 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.
• Client Consulting & Relationship Management 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.
• Market & Carrier Engagement 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.
• Collaboration & Internal Alignment 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.

Benefits

• Competitive base salary plus performance-based incentive compensation.
• Comprehensive benefits package including medical, dental, vision, retirement plan, and paid time off.
• Professional development and continuing education support.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed
• Number of Employees: 1,001-5,000 employees