Senior Sales Representative (Enterprise Insurance Agencies)

EnrollHere is on a mission to make healthcare enrollment simple, transparent, and accessible for everyone. We partner with organizations nationwide to deliver streamlined technology and exceptional customer experiences, ensuring members can access the coverage they need with confidence. Our fully remote team thrives on collaboration, innovation, and a shared commitment to improving the enrollment journey for all.

The Senior Sales Representative role focuses on selling to large, multi-location enterprise insurance agencies and brokerages, including national and regional firms. You’ll drive new logo acquisition and expansion by helping agencies modernize sales, marketing, compliance, and reporting operations through our SaaS platform.

Responsibilities

• Lead full-cycle enterprise sales motions with large agency organizations
• Sell into agency leadership (owners, CROs, COOs, heads of compliance and sales)
• Articulate clear ROI around productivity, compliance, lead monetization, and growth
• Manage complex buying groups across sales, compliance, IT, and finance
• Partner with Customer Success to ensure smooth onboarding and long-term account growth
• Maintain accurate forecasting and pipeline discipline
• Contribute feedback to Product and GTM teams based on agency market needs

What Success Looks Like

• Consistent enterprise deal wins and renewals
• Strong agency references and case studies
• Expansion into multi-line, multi-office agency accounts