Vice President of Commercial Sales

Who you are

• 5+ years of B2B sales experience with documented quota attainment in complex, long-cycle environments
• 10+ years specifically selling to HR/benefits decision-makers in enterprise accounts (1,000+ employees preferred)
• Proven track record closing multiple deals with annual contract values of $500K+ (must provide specific examples)
• Direct experience in one or more of these domains: healthcare/benefits sales (health plans, wellness programs, digital health), insurance/broker channel sales, or HR technology sales
• Demonstrated CRM proficiency (Salesforce or equivalent) with strong documentation discipline and forecast accuracy
• Experience managing 12+ month sales cycles with seasonal buying patterns and navigating complex procurement processes
• Ability to travel approximately 50% and authorization to work in the United States
• You're a market developer, not an order-taker: You've created non-traditional pipeline sources (like partnerships that generated 40%+ of opportunities), identified market triggers before competitors, and developed sophisticated territory strategies beyond basic segmentation
• You excel at stakeholder orchestration: You've successfully recovered deals after initial rejection by re-engaging through different stakeholders, and you naturally adapt your pitch for CFOs (financial impact), CHROs (employee experience), and clinical leaders (quality outcomes)
• You think like a consultant: You've built business cases that survived CFO scrutiny, designed creative deal structures to overcome obstacles, and uncovered non-obvious pain points through structured discovery—going far beyond surface-level cost concerns
• You're a collaborator who elevates the team: You document deals comprehensively so Finance, Legal, Operations, and Client Services have what they need; you bring back market intelligence from the field; and you've created playbooks or tools that improved team performance
• You bring existing relationships: You have an established network of benefits consultants, brokers, or enterprise contacts you can activate in this role

What the job involves

• Galileo is transforming how America's workforce experiences healthcare, and we need an exceptional enterprise sales leader to accelerate our expansion. This role owns the full sales cycle with mid-to-large employers (1,000+ employees), partnering with benefits consultants and brokers to replace fragmented, frustrating healthcare with our virtual-first primary care platform
• You'll be equal parts strategist, consultant, and closer—building a territory from the ground up while directly impacting how hundreds of thousands of employees access quality care
• You'll spend significant time developing your strategy—researching target accounts, mapping stakeholder landscapes, nurturing broker/consultant relationships, and orchestrating multi-threaded sales campaigns that position Galileo ahead of competitors
• Equally important is the consultative aspect of the role: you'll lead discovery conversations with CFOs, CHROs, and benefits teams to diagnose their healthcare challenges, architect custom solutions, and build business cases that survive executive scrutiny
• You'll balance independent pipeline development with intensive cross-functional collaboration—partnering with Finance on deal modeling, Legal on contract terms, and Operations on implementation planning—always connecting your work to transforming healthcare delivery for working families
• Own and build: Develop and execute a multi-year account acquisition strategy for your assigned region/vertical, creating multiple pipeline sources including direct outreach, broker/consultant partnerships, and market trigger identification
• Drive complex enterprise sales cycles: Manage 12+ month sales processes from initial contact through contract signature, orchestrating engagement across 5-10 stakeholders with competing priorities (C-suite, HR, finance, clinical teams)
• Build and leverage strategic partnerships: Cultivate relationships with benefits consultants, brokers, and industry influencers who generate recurring qualified opportunities and advocate for Galileo in competitive evaluations
• Deliver consultative solutions: Lead structured discovery to uncover employer pain points, translate clinical outcomes into financial ROI, and design deal structures that overcome budget and timing obstacles
• Forecast and report accurately: Maintain disciplined CRM hygiene in Salesforce, provide reliable monthly/quarterly revenue forecasts, and create comprehensive deal documentation that enables seamless cross-functional execution
• Contribute market intelligence: Serve as a feedback loop to product, marketing, and leadership on competitive dynamics, messaging effectiveness, and emerging customer needs based on frontline insights
• Ensure successful client launches: Partner with Operations, Finance, Legal, and Client Services throughout the deal lifecycle to align on implementation requirements, success KPIs, and long-term account strategy