Vice President, Sales

Full-time; US office (remote)


HighRoads is the industry leader in sales-enabling health plan product management. Our cloud-based technology empowers our health plan clients to quickly configure and sell innovative compliant products that meet customer needs and differentiate them from the competition.

Position Summary/Scope

This role will report directly to the Senior Vice President, Sales, Tim Herlehy. The VP, Sales will be responsible for expanding HighRoads’ market share by selling new business to healthcare payers of all types and sizes. The primary success factors for this role are securing new payer logos and generating revenue for the company.

Responsibilities/Success Factors

Specifically, the VP, Sales will be expected to:

  • Build a pipeline of new opportunities within the healthcare payer market.
  • Secure new business within the healthcare payer market.
  • Generate revenue for the company.

Ideal Qualifications

  • A minimum of 5 years of a superior track record in new business sales execution within leading healthcare technology organizations, selling software and services to the senior management of payers.
  • Keen understanding of the art and science of selling as it relates to process, accountability, and forecasting; building and nurturing relationships; positively influencing decisions; and delivering and receiving feedback with both internal and external constituents.
  • A combination of large corporate and small rapid-growth company experience is highly preferred. Knowledge of sophisticated management and operational systems found in the larger, established health information and strategic consulting leaders, combined with the demonstrated ability to operate effectively in a smaller company. Experience in a fast moving, entrepreneurial environment during a period of rapid growth and expansion. Experience taking a technology solution to market and achieving its adoption and acceptance within the payer marketplace.
  • Ability to deal with the inevitable objections to the adoption of innovative solutions within client organizations. A proven and passionate driver of transformation.
  • A self-starter who can conceive of and drive the adoption of new initiatives up, down, and across large organizations. Ability and authority to gain the confidence of senior executives at the C-suite within the payer community. Confident with emphasis on building trust and enduring relationships.
  • Experience with missionary sales of cutting edge, technology driven products and services. Significant success in multi-level, cross-functional, enterprise-wide selling. Comfortable with technology – engineering or other technical background is a plus.
  • An optimistic and enthusiastic nature combined with a grounded, realistic and mature perspective and a reputation for integrity.

Ideal Personal Characteristics

  • A Focus on Execution. A self-starter with a bias for action. A non-political team player who can quickly establish himself/herself as a trusted member of the team and can be relied upon to get things done.
  • Company Focused. Someone who identifies closely with and is committed to the achievement of the Company’s mission while working in concert with other groups internally and externally.
  • Nimble in the Face of Ambiguity and Adversity. A hands-on, entrepreneurial executive able to seize upon moving windows of opportunity in evolving market segments. Grounded/pragmatic; someone who naturally adjusts to changing internal/external dynamics, priorities and challenges. Decisive optimist / “can-do” attitude; values people and focuses on “doing the right thing”.
  • Energetic and Optimistic. HighRoads is a dynamic, innovative company with a “can-do” culture. It wants leaders who continue to build on this culture.
  • “Equity” Mindset. The successful candidate will have a proven ability to pursue his/her objectives passionately with an ownership mentality and a focus on the overall success of the Company and increasing shareholder value. Able to function effectively in a high risk/reward scenario.
  • Maturity and Independence. Someone who speaks with authority and leads rather than follows. A highly ethical and intelligent professional with the executive presence and industry stature to effectively represent the company and its mission externally, and to bring enhanced credibility to the firm and its products. A thoroughly honest and forthright individual who is up-front and direct with subordinates, peers and top management executives.


Report to the corporate US office in Burlington, MA. Position can be remote.

Questions? Please email

Ready to Apply? Please submit your resume and cover letter to

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