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Vice President of Sales (Enterprise)

Function

Skills

Required

  • pricing strategy
  • contract structuring

Preferred

  • driving complex sales cycles

Function as the Vice President of Sales - Enterprise, where you will be responsible for acquiring and growing relationships with the largest employers in the country. This senior individual contributor role will involve driving complex, multi-stakeholder sales cycles across Fortune 500-scale organizations and leading benefits consulting firms. You will own the full lifecycle of the sales process, build and manage relationships with executive stakeholders, and partner cross-functionally to design optimized programs. Additionally, you will ensure successful enterprise rollout and activation, achieve quarterly and annual quotas, and operate with urgency and discipline in a fast-paced, high-growth environment.

Responsibilities

  • Acquiring and growing relationships with large employers, driving complex sales cycles.
  • Owning the full lifecycle of the sales process, from initial engagement to contract execution.

Requirements

  • Building and managing relationships with executive stakeholders, developing long-term strategic partnerships.

Highly collaborative, low ego, and team-oriented

  • Proven track record of closing large, complex deals with national or jumbo employers
  • Strong commercial acumen, including pricing strategy, negotiation, and contract structuring

Thrives in ambiguity and fast-paced environments

  • Ability to operate independently as a senior IC while partnering cross-functionally
  • Operates with urgency, accountability, and a high bar for excellence
  • High ownership mindset with a bias toward action and results
  • Experience working in high-growth or venture-backed environments
  • 10–12+ years of enterprise sales experience in benefits, healthcare, or HR technology

Mission-driven with a strong belief in transforming healthcare

  • Demonstrated success navigating multi-stakeholder, executive-level sales cycles
  • Deep relationships with major consulting firms (e.g., Marsh McLennan, Mercer, WTW, Aon, Gallagher)

Preferred

  • Experience selling preventative health, population health, or clinical programs is preferred
  • Background in B2B2C or employer-sponsored healthcare models