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

Qualifications

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

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

Benefits

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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