Enterprise Sales Leader - Healthcare Transformation

About the Role

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.

A Day in the Life

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.

Key Responsibilities

• 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

Must-Have Qualifications

• 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

What Makes You Stand Out

• 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

Benefits & Why Join Us

What You'll Gain:

• Ownership: Build something from the ground up with entrepreneurial autonomy while backed by a proven platform
• Mission-driven impact: Every deal you close improves healthcare access for thousands of employees and their families
• Strategic influence: Your market insights will directly shape Galileo's product, positioning, and go-to-market strategy

Compensation: Competitive salary and benefits package.