Senior Sales Representative (Insurance Carriers)

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.

This Senior Sales Representative will own and grow relationships with insurance carriers, selling enterprise-grade insurtech solutions that improve distribution, compliance, analytics, and operational efficiency. This is a consultative, strategic sales role requiring deep industry fluency.

Responsibilities

• Own full-cycle sales for carrier accounts, from prospecting to close
• Develop executive-level relationships across product, compliance, operations, and growth teams
• Navigate long, complex sales cycles with multiple stakeholders and decision makers
• Position platform value across carrier priorities: growth, compliance, efficiency, and reporting
• Collaborate with Solutions Engineering, Product, and Customer Success to win and expand accounts
• Build accurate forecasts and maintain disciplined pipeline management
• Represent the company at industry conferences and carrier-focused events

What Success Looks Like

• Closed-won enterprise carrier deals with strong ACVs
• Expansion within existing carrier accounts
• Trusted advisor status with senior carrier leaders

Requirements

• 7+ years of enterprise B2B sales experience
• Proven success selling into insurance carriers or highly regulated enterprises
• Strong understanding of carrier economics, compliance pressures, and distribution models
• Experience selling SaaS platforms with integrations, data, or workflow complexity
• Executive-presence and comfort selling at the VP/SVP/C-suite level

Benefits

We believe in taking care of our team, which is why we offer a comprehensive benefits package that supports your health, wellness, and future:

• Medical: 4 United Healthcare medical plans (including an HSA option)
• Dental: 3 dental plans (Aetna and MetLife)
• Vision: 2 Aetna vision plans
• Wellness & Mental Health: 5 additional Medical Plus benefits, including telehealth support and an annual Talkspace subscription
• Ancillary Coverage: 4 ancillary plans and supplemental life insurance
• Retirement: 401(k) with a 4% match (after a 90-day exclusionary period)
• PTO & Flexibility: Generous PTO and remote work support
• Growth: Learning stipends and opportunities for professional development