Castlight Health · 13 hours ago
Regional Director of Sales, Employer
United States
Full-time
Remote
Director/Executive
$171K/yr - $256K/yr
8+ years expCastlight Health is seeking a results-driven Regional Director of Sales with deep experience in healthcare technology and SaaS sales. The role involves driving new business sales across a multi-state region focused on large employers, managing a robust pipeline, and collaborating with internal teams to align client needs with product capabilities.
EnterpriseFitnessHealth CareInformation TechnologyWellness
Responsibilities
Drive new business sales across a multi-state region, focused on large employers with over 1,000 employees
Manage a robust pipeline and lead opportunities through a consultative and strategic sales process
Consistently exceed quota through high-impact prospecting, solution selling, and strategic territory planning
Develop and execute a territory strategy that leverages relationships with key stakeholders including benefit leaders, consultants, and strategic alliance partners
Collaborate closely with internal cross-functional teams including Marketing, Product, and Customer Success to align on client needs and product capabilities
Maintain expert-level knowledge of company solutions, including healthcare navigation and advocacy platforms
Build and nurture strategic relationships with benefits consultants, point solution partners, buying consortia, and other key influencers
Provide accurate forecasting and regular pipeline reporting to senior leadership
Represent the company at industry events, trade shows, and webinars as a thought leader and subject matter expert
Qualification
Required
Deep experience in healthcare technology and SaaS sales, particularly in selling into large employers (1,000+ employees)
Proven track record of success in healthcare navigation and advocacy solutions
Skilled at managing complex sales cycles involving multiple stakeholders
Record of successfully meeting and exceeding quota
Hunter mentality that can build top of funnel while driving opportunities to close
Drive new business sales across a multi-state region, focused on large employers with over 1,000 employees
Manage a robust pipeline and lead opportunities through a consultative and strategic sales process
Consistently exceed quota through high-impact prospecting, solution selling, and strategic territory planning
Develop and execute a territory strategy that leverages relationships with key stakeholders including benefit leaders, consultants, and strategic alliance partners
Collaborate closely with internal cross-functional teams including Marketing, Product, and Customer Success to align on client needs and product capabilities
Maintain expert-level knowledge of company solutions, including healthcare navigation and advocacy platforms
Build and nurture strategic relationships with benefits consultants, point solution partners, buying consortia, and other key influencers
Provide accurate forecasting and regular pipeline reporting to senior leadership
Represent the company at industry events, trade shows, and webinars as a thought leader and subject matter expert
Bachelor's degree required
Experience with enterprise sales cycles of 6-12+ months
Knowledge of healthcare benefits trends and employer-sponsored benefits strategies
Experience working with or selling alongside ecosystem partners such as TPAs, carriers, and digital health vendors
Preferred
8+ years of successful sales experience in healthcare technology or SaaS, with a focus on selling to large employers
Demonstrated success in selling healthcare navigation, advocacy, or related benefits solutions
Strong relationships and experience working with benefit consultants and other ecosystem partners
Track record of consistently meeting or exceeding sales quotas
Highly skilled in territory management, consultative selling, and strategic account planning
Exceptional communication, negotiation, and presentation skills
Comfortable navigating complex sales environments with multiple decision-makers
MBA or relevant advanced degree a plus
Benefits
This position is bonus eligible based on individual and company performance.
Company
Castlight Health
Castlight Health provides a healthcare navigation platform with resources for benefits, and vendors.
501-1000 employees
Funding
Current Stage
Public CompanyTotal Funding
$184.1MKey Investors
Maverick VenturesVenrock
2022-01-05Acquired
2015-06-25Post Ipo Equity· $3.1M
2014-03-14IPO
Leadership Team
Vijay Anand
Executive Vice President of R&D
Recent News
2026-01-05
2025-12-19
2025-12-09
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