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