Vice President of Sales (Enterprise)

• The Vice President, Sales – Enterprise is responsible for acquiring and growing relationships with the largest employers in the country (15,000+ employees)
• This is a senior individual contributor role focused on driving complex, multi-stakeholder sales cycles across Fortune 500–scale organizations and leading benefits consulting firms
• You will own the full lifecycle—from initial engagement through contract execution and early expansion—while serving as a strategic partner to executive stakeholders
• This is one of Function’s most high-impact roles, directly shaping our enterprise growth trajectory and long-term market presence
• 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

Benefits

• 401k Match
• Health Insurance
• Choose your own holidays

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