The role involves driving sales to large insurance agencies by managing complex buying groups, articulating ROI, and ensuring smooth onboarding with Customer Success. Success is measured by consistent deal wins and growth in multi-line agency accounts.
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
- Consistent enterprise deal wins and renewals
- Strong agency references and case studies
- Expansion into multi-line, multi-office agency accounts
Requirements
- 7+ years of B2B SaaS sales experience
- Direct experience selling to large insurance agencies or brokerages
- Strong understanding of agency distribution models and producer workflows
- Proven ability to close six-figure+ ACV deals
- Consultative selling mindset with strong business acumen
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
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