[Hiring] VP, Commercial Sales @Galileo

Role Description

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:

• Develop your strategy—researching target accounts, mapping stakeholder landscapes, nurturing broker/consultant relationships, and orchestrating multi-threaded sales campaigns.
• Lead discovery conversations with CFOs, CHROs, and benefits teams to diagnose healthcare challenges, architect custom solutions, and build business cases.
• Balance independent pipeline development with intensive cross-functional collaboration—partnering with Finance, Legal, and Operations.

Key Responsibilities

• Own and build: Develop and execute a multi-year account acquisition strategy for your assigned region/vertical.
• Drive complex enterprise sales cycles: Manage 12+ month sales processes from initial contact through contract signature.
• Build and leverage strategic partnerships: Cultivate relationships with benefits consultants, brokers, and industry influencers.
• Deliver consultative solutions: Lead structured discovery to uncover employer pain points and design deal structures.
• Forecast and report accurately: Maintain disciplined CRM hygiene in Salesforce and provide reliable revenue forecasts.
• Contribute market intelligence: Serve as a feedback loop to product, marketing, and leadership on competitive dynamics.
• Ensure successful client launches: Partner with Operations, Finance, Legal, and Client Services throughout the deal lifecycle.

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+.
• Direct experience in healthcare/benefits sales, insurance/broker channel sales, or HR technology sales.
• Demonstrated CRM proficiency (Salesforce or equivalent) with strong documentation discipline.
• Experience managing 12+ month sales cycles with seasonal buying patterns.
• 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 excel at stakeholder orchestration.
• You think like a consultant.
• You're a collaborator who elevates the team.
• You bring existing relationships.

Benefits

• Ownership: Build something from the ground up with entrepreneurial autonomy.
• Mission-driven impact: Every deal you close improves healthcare access for thousands of employees.
• Strategic influence: Your market insights will directly shape Galileo's product and strategy.
• Compensation: $150,000 - $200,000 per year based on experience, with OTE of ~$350,000–$400,000.
• Comprehensive Benefits Package:
• Medical / Dental / Vision insurance
• Flexible Spending Account
• Health Savings Account + match
• Company paid STD/LTD, AD&D, and Life insurance
• Paid Family Leave
• 401K + match
• Paid Time Off