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Enterprise Sales Director

Enterprise Sales Director

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Role Overview

We have an exciting opportunity for a Regional Sales Director during a unique time of significant growth. We are looking for a strategic sales leader who is passionate about growth, innovation and revolutionizing healthcare.  Reporting to the Vice President of Sales, this role will be responsible for the development and management of a designated region. This will include leading, directing and managing activities of Sales Representatives within a specific geographical area as well as leading his/her team to the achievement of established business objectives.

A Day in the Life

A Day in the life….

  • Lead, manage and develop the skill sets and overall performance of the sales representatives in his or her Regional Business.
  • Hire, train, develop and coach new and existing sales representatives.
  • Develop and implement approved business plans to contribute to overall sales success.
  • Achieve organizational objectives through effective leadership and forecasting of opportunities.
  • Effectively identify/monitor multiple local market conditions and build strong customer relationships.
  • Monitor all field activities to make certain all are within compliance guidelines.

Other accountabilities will involve:

  • Ensure appropriate delivery of marketing and sales tactics in Region.
  • Collaborate on development of goals and objectives at all levels and build appropriate measures to ensure achievement.
  • Oversee the recruiting, interviewing, hiring, training and staffing of the sales team.
  • Provide frequent and ongoing performance feedback to all direct reports and foster a team oriented and supportive working environment.
  • Establish performance expectations and oversee activity of direct reports, including adherence to policies.
  • Oversee performance management process for all team members and ensure fair, timely resolution of disciplinary issues.
  • Foster an environment that rewards accomplishment and encourages the advancement and retention of productive employees.

Demonstrated education, skills and experience to be successful in this role:

  • BA in a business or technical related area of study
  • Minimum 5 years of strategic selling experience
  • Minimum of 6-8 years of successful sales leadership experience
  • Experience selling complex, multi-stakeholder solutions. SaaS, health & welfare benefits, healthcare capital equipment, healthcare IT, health and welfare benefits outsourcing, human resources IT benefits software
  • Proven and established relationships with Executives (VP, C Level)
  • You should be a “hunter” with proven experience in running long, complex B2B sales cycle processes for large companies and proven track record of closing large complex deals. 
  • Ability to pass a background check


Values we admire:

  • We find joy and purpose in serving others.
    • Making a difference is what we do. We do the right thing for the right reasons – and we do it well, even when it’s hard.
    • You operate from a perspective of truly caring about our employees, clients, and customers and creating value for them.
  • We are strong individually and together, we’re powerful.
    • We believe in each other, in honesty, and in having fun. You won’t find egos or office walls here because we aren’t defined by titles – but by actions, behaviors and results.
  • We roll up our sleeves and get stuff done.
    • Being wildly successful is more than just a goal – it’s a serious commitment.
    • We’re disciplined, purpose-driven, and accountable for our results. Results motivate us. And we aren’t afraid of the hard work or tough decisions that get us there.
  • We’re boldly and relentlessly reinventing healthcare.
    • We are a company changing the world, one person at a time.
    • Super high expectations? Bring it on? Our curiosity drives us.
  • You understand our desire to be the best place to work and that trust is the foundation of that.

Who we Are

Where it all began…

Accolade is an on-demand healthcare concierge for employers, health plans, health systems and consumers. Our team of compassionate, exceptional professionals is supported by breakthrough science and technologies to guide people through the healthcare system in a deeply personalized manner. By taking the time to get to know each person, understand the context of their healthcare decisions, build trust and influence decisions, we deliver industry-leading engagement levels, satisfaction scores unseen in healthcare, better health outcomes, and cost savings of more than 10 percent.


Accolade has been recognized as one of the nation’s 25 most promising companies by Forbes magazine, the fastest-growing private healthcare company by Inc. 500 and a Top Workplace in Philadelphia for five consecutive years. For more information, visit

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