Sales Director


HealthSherpa faces a critical business problem and needs an inspired salesperson to help solve the next generation of go-to-market problems. If you're successful, HS will be a $10B business. We are already a profitable, fast-growing business with nearly 9 figures of revenue, but that's just a drop in the bucket compared to the $40B+ that is transacted in our marketplace. Helping create and capture billions more in value will be your goal. For the right person, this is the opportunity of a lifetime.

You will report to the VP of Sales and Distribution.

You Will:

  • Collaborate with Product teams to develop and bring new products to market
  • Target and hit ambitious personal and organizational enrollment and revenue goals
  • Overcome objections, driving customer buying decisions
  • Understand markets and our competitors
  • Achieve and exceed assigned quotas for assigned market geography
  • Build market sales plan to achieve metrics
  • Broaden carrier adoption, understanding, and use of HealthSherpa's platform

You Have:

  • At least 5 years of direct sales experience selling into multi-stakeholder enterprise organizations
  • Experience solutioning with Product to meet gaps in customer needs
  • Demonstrated effectiveness communicating with senior business leaders (written and oral), with the ability to reconcile competing points of view
  • Insurance carrier sales or SaaS experience is a bonus
  • Bilingual ability (Spanish preferred) is also a bonus

What We Offer:

  • Remote-first company
  • Great compensation package with meaningful equity in a high growth, profitable company
  • Excellent benefits package that includes health, vision, and dental coverage for you, your spouse and dependents
  • Monthly grocery stipend and home internet reimbursement
  • 401K w/ a match after a grace period
  • Employee assistance program
  • Parental leave
  • 4 weeks paid vacation in addition to paid holidays
  • Home office budget for remote team members
  • Disability insurance

We're building a diverse and inclusive work environment where we learn from each other. We welcome and encourage people of diverse backgrounds, experiences, identities, abilities and perspectives to apply. We are an equal opportunity employer and a fun place to work.

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