Regional Director of Sales, Employer

Regional Director of Sales

We are seeking a results-driven regional director of sales with deep experience in healthcare technology and SaaS sales, particularly in selling into large employers (1,000+ employees). The ideal candidate has a proven track record of success in healthcare navigation and advocacy solutions and is skilled at managing complex sales cycles involving multiple stakeholders.

This is a remote position; however candidates located in Eastern or Central time zones are preferred.

Key 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.

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.

Requirements:

• 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.

Compensation range: $ to $