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Vice President (VP) of Sales – Enterprise (East & West)

United StatesRemote10+ YOE
Summary

Leads end-to-end sales cycles for enterprise employers (15,000+ employees), managing complex multi-stakeholder deals, executive relationships, and expansions in healthcare/benefits. Requires 10-12+ years experience closing large deals with Fortune 500-scale organizations.

About the role

Responsibilities

Enterprise Sales Ownership

  • Own the end-to-end sales cycle for national and jumbo employers (15,000+ employees).
  • Drive complex, multi-threaded deals across HR, Total Rewards, Clinical, and Finance stakeholders.
  • Lead RFP processes, pricing strategy, and contract negotiations.

Executive Relationship Management

  • Build and manage relationships with CHROs, Chief Medical Officers, CFOs, and senior decision-makers.
  • Develop long-term strategic partnerships aligned to employer health and wellbeing initiatives.
  • Navigate and influence key benefits consulting firms and broker relationships.

Program Design & Commercial Strategy

  • Partner cross-functionally to design clinically and financially optimized programs.
  • Structure multi-year agreements and full-population deployments.
  • Guide employers toward preventative-first, high-impact benefit models.

Enterprise Launch & Early Expansion

  • Partner with Customer Success to ensure successful enterprise rollout and activation.
  • Own expansion opportunities within the first 6–9 months post-launch.
  • Identify and close growth opportunities across geographies, populations, and product lines.

Performance & Quota

  • Achieve quarterly and annual quotas aligned to 3–4 new enterprise logos per year.
  • Manage pipeline, forecasting, and deal progression with high accuracy.
  • Operate with urgency and discipline in a fast-paced, high-growth environment.

Qualifications / Skills

  • 10–12+ years of enterprise sales experience in benefits, healthcare, or HR technology.
  • Proven track record of closing large, complex deals with national or jumbo employers.
  • Deep relationships with major consulting firms (e.g., Marsh McLennan, Mercer, WTW, Aon, Gallagher).
  • Demonstrated success navigating multi-stakeholder, executive-level sales cycles.
  • Strong commercial acumen, including pricing strategy, negotiation, and contract structuring.
  • Ability to operate independently as a senior IC while partnering cross-functionally.
  • High ownership mindset with a bias toward action and results.
  • Experience selling preventative health, population health, or clinical programs is preferred.
  • Background in B2B2C or employer-sponsored healthcare models.
  • Experience working in high-growth or venture-backed environments.
Skills
Enterprise SalesRFP ProcessesPricing StrategyContract NegotiationPipeline ManagementForecastingSalesforceHR TechnologyHealthcare SalesBenefits Sales