Director/Sr. Director of Employer Sales

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Director/Sr. Director of Employer Sales based in the United States.

This is a high-impact sales leadership opportunity focused on driving national employer growth in the digital healthcare space.
You’ll own a territory, revenue target, and the full enterprise sales cycle from prospecting through contract execution.
The role centers on building relationships with HR, Benefits, Total Rewards, and C-suite decision-makers.
You’ll leverage an established network of employers, brokers, consultants, and health plans to create and accelerate opportunities.
As a true hunter and closer, you’ll shape the employer sales strategy while personally driving complex deals to completion.
You’ll also bring market intelligence back to the organization and help refine scalable sales processes and playbooks.
The role offers significant autonomy, meaningful revenue ownership, and the opportunity to contribute to better healthcare for women in midlife.

• Own a national employer territory and revenue target, developing and executing a focused strategy to identify, engage, and convert ideal customer accounts.
• Build and maintain a high-quality pipeline through proactive prospecting, creative outreach, industry relationships, and targeted account development.
• Lead complex, multi-stakeholder sales cycles from initial engagement through executive presentations, negotiation, contracting, and close.
• Build trusted relationships with HR, Benefits, Total Rewards, and executive-level buyers while developing internal champions and navigating organizational decision-making.
• Leverage relationships across employers, brokers, benefits consultants, and health plans to create opportunities, accelerate sales cycles, and maximize deal value.
• Deliver consultative, compelling presentations that connect the organization’s value proposition to employer priorities, workforce needs, and the competitive landscape.
• Maintain rigorous sales discipline through accurate forecasting, CRM hygiene, follow-up, pipeline management, and detailed deal tracking in HubSpot.
• Share buyer, market, and competitive insights internally and collaborate cross-functionally to strengthen the employer sales motion and continuously improve sales playbooks.
• Represent the organization at relevant industry events and customer engagements, with approximately 20–25% travel expected.

Requirements

• 10+ years of experience in employer healthcare benefits sales, ideally within digital health, healthcare services, or another high-growth environment.
• Demonstrated success consistently meeting or exceeding sales quotas and personally closing complex employer healthcare or benefits deals.
• Established relationships across the HR and employee benefits ecosystem, including a strong network of employers, brokers, and consultants.
• Proven ability to originate opportunities, prospect effectively, build executive relationships, and personally drive enterprise deals through to close.
• Experience navigating complex organizations and influencing stakeholders from Director-level buyers through C-suite executives.
• Strong understanding of the employer benefits ecosystem and the roles played by employers, brokers, consultants, and health plans.
• Highly organized and commercially disciplined, with strong forecasting, CRM management, follow-up, and pipeline-management skills.
• Excellent written, verbal, presentation, negotiation, and relationship-building capabilities.
• Ability to work independently while collaborating effectively with cross-functional teams in a fast-paced, high-growth environment.
• Self-directed, resilient, resourceful, and motivated by ambitious goals and meaningful commercial outcomes.
• Passion for improving healthcare for women and enthusiasm for contributing to a mission-driven organization.
• Must be authorized to work in the United States without current or future visa sponsorship.

Benefits

• Base salary of $160,000–$225,000 per year, depending on experience, skills, and qualifications.
• Eligibility for additional variable compensation tied to performance.
• Meaningful equity participation and the opportunity to share in the company’s growth.
• Comprehensive benefits package.
• Remote work from anywhere in the United States.
• Mission-driven, high-ownership environment with a nationally distributed team.
• Opportunity to build a category-defining employer sales channel and directly influence meaningful revenue growth.
• Opportunity to help shape sales strategy, processes, and playbooks as the organization scales nationally.
• Approximately 20–25% travel for customer, industry, and business engagements.
• Inclusive workplace committed to equal opportunity and pay equity.
• Opportunity to contribute to improving healthcare for women navigating midlife health challenges.

We use an AI-powered matching process to ensure your application is reviewed quickly, objectively, and fairly against the role's core requirements. Our system identifies the top-fitting candidates, and this shortlist is then shared directly with the hiring company. The final decision and next steps (interviews, assessments) are managed by their internal team.

We appreciate your interest and wish you the best!

Why Apply Through Jobgether?

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