Enterprise Sales Leader – Healthcare Solutions

About Us: Galileo is a team-based medical practice working to improve the quality and affordability of healthcare across 50 states. Operating with a data-driven, multi-specialty approach, Galileo provides high-touch, longitudinal care to diverse and complex patients—both virtually and in-person. Founded by Dr. Tom X. Lee, a pioneer behind One Medical and Epocrates, Galileo combines healthcare, technology, and human-centered design to transform society by solving its largest healthcare challenges while improving patient-provider relationships.

About the Role: Galileo is revolutionizing how America’s workforce experiences healthcare, and they are seeking an exceptional enterprise sales leader to accelerate their expansion. This role involves owning the full sales cycle with mid-to-large employers (1,000+ employees), collaborating with benefits consultants and brokers to replace fragmented healthcare solutions with their virtual-first primary care platform. You’ll act as a strategist, consultant, and closer, building a territory from the ground up and directly impacting the healthcare access of hundreds of thousands of employees.

A Day in the Life: Your responsibilities will include developing a strategic sales approach—researching target accounts, mapping stakeholder landscapes, nurturing broker/consultant relationships, and orchestrating multi-threaded sales campaigns. You’ll also lead consultative discovery conversations with CFOs, CHROs, and benefits teams to diagnose their healthcare challenges, design custom solutions, and build business cases that withstand executive scrutiny. Additionally, you’ll balance independent pipeline development with cross-functional collaboration, partnering with Finance, Legal, and Operations to ensure seamless implementation planning.

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, engaging 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 to 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 for seamless cross-functional execution.
• Contribute market intelligence: Provide feedback 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 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).
• A proven track record of 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, 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) and developed sophisticated territory strategies.
• You excel at stakeholder orchestration: You’ve successfully recovered deals after initial rejection by re-engaging through different stakeholders and adapt your pitch for CFOs, CHROs, and clinical leaders.
• You think like a consultant: You’ve built business cases that survived CFO scrutiny, designed creative deal structures, and uncovered non-obvious pain points.
• You’re a collaborator who elevates the team: You document deals comprehensively and bring back market intelligence from the field, creating playbooks or tools that improved team performance.
• You bring existing relationships: You have an established network of benefits consultants, brokers, or enterprise contacts.