Gem.com

Account Executive - Lower Mid-Market (East & West)

Gem.com$80K — $120K *
Healthcare
5 - 7 years of experience
Job Overview by Ladders

Qualifications

  • 5-8+ years of B2B sales experience, ideally in health benefits, digital health, or employee wellbeing.
  • Proven track record of exceeding quotas in mid-market sales.
  • Experience selling to HR, Total Rewards, and benefits consultants preferred.
  • Strong consultative and solution-oriented sales skills.
  • Ability to operate autonomously in a fast-scaling environment.

Responsibilities

  • Own the entire sales cycle for employers with 500-4,999 employees.
  • Prospect, qualify, and build pipeline through brokers, consultants, and direct channels.
  • Deliver compelling consultative presentations to HR, Benefits, and Total Rewards leaders.
  • Partner with sales engineering, product, clinical, and leadership resources to shape customer solutions.
  • Ensure strong activation and employee engagement at launch by collaborating with Customer Success.
  • Drive first-year success metrics, focusing on adoption and program design quality.
  • Promote strong employer plan design and optimize contracts, leveraging bonus structures.

Benefits

  • Strong incentives tied to new employer acquisition and activation.
  • Opportunity to shape customer solutions in a consultative manner.
  • Support from cross-functional teams including sales engineering and clinical resources.
  • Potential for career advancement within a rapidly scaling company.
Full Job Description
Segments Covered: Employers with 500-4,999 employees

Role Type: Individual Contributor (IC)

About the Role

The Director of Sales, Lower Mid-Market (LMM) segment is responsible for acquiring new employer customers and driving Function Health adoption across companies with 500-4,999 employees. This role is designed to mirror benefits-industry norms, signaling experience and credibility with HR and Total Rewards leaders. You will be responsible for full-cycle sales-from prospecting to contract execution to launch partnership-with clear incentives tied to new employer acquisition, strong activation, and high-quality plan design.

Responsibilities

New Logo Acquisition

  • Own the entire sales cycle for employers in the 500-4,999 employee range.
  • Prospect, qualify, and build pipeline through brokers, consultants, and direct channels.
  • Deliver compelling consultative presentations to HR, Benefits, and Total Rewards leaders.
  • Partner with sales engineering, product, clinical, and leadership resources to shape customer solutions.


Activation & Launch Success

  • Work with Customer Success to ensure strong activation and employee engagement at launch.
  • Drive first-year success metrics, including adoption and program design quality.


Plan Design & Contract Optimization

  • Promote strong employer plan design, including:
    • Full subsidy or first-dollar preventive coverage
    • Multi-year agreements
    • Eligibility expansion beyond initial pilots
    • Leverage bonus kickers tied to subsidy decisions and contract structure.


Expansion Ownership (Months 0-9)

  • Earn expansion credit for:
    • Adding new employee groups
    • Converting pilots or executive-only programs to full population
    • Moving from voluntary programs to subsidized programs


Quota & Performance Expectations

  • Quarterly quotas aligned to the annual target of 10-14 new logos per year.
  • Ramp period:
    • Q1: 50% quota
    • Q2: 75% quota
    • Q3+: Full quota


Qualifications

  • 5-8+ years of B2B sales experience, ideally in health benefits, digital health, or employee wellbeing.
  • Track record of exceeding quota in mid-market sales.
  • Experience selling into HR, Total Rewards, and benefits consultants preferred.
  • Strong consultative and solution-oriented sales skills.
  • Ability to operate autonomously in a fast-scaling environment.


About Gem.com

Industry
Founded
2013

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