Regional Director of Sales
Castlight Health
full-time
Posted on:
Location Type: Remote
Location: United States
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Salary
💰 $170,616 - $255,925 per year
Job Level
About the role
- 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.
Requirements
- 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.
- Bachelor’s degree required; MBA or relevant advanced degree a plus.
- 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.
Benefits
- This position is bonus eligible based on individual and company performance.
Applicant Tracking System Keywords
Tip: use these terms in your resume and cover letter to boost ATS matches.
Hard Skills & Tools
sales experiencehealthcare technologySaaShealthcare navigationadvocacy solutionsterritory managementconsultative sellingstrategic account planningpipeline reportingenterprise sales cycles
Soft Skills
communication skillsnegotiation skillspresentation skillsrelationship buildingstrategic thinkingconsultative approachcollaborationforecastingproblem-solvinginfluencing skills
Certifications
Bachelor's degreeMBA