Enterprise Sales VP, Labor and Trust

About This Opportunity

We are representing a confidential healthcare technology client in their search for an Enterprise Sales VP, Labor and Trust. This is a remote, individual contributor role focused on expanding market share within large labor health and welfare funds across a defined national territory.

Our client partners with employers to improve healthcare outcomes through data-driven provider performance analytics. They work with over 2.5 million members and have achieved significant growth year-over-year. This role offers the opportunity to drive measurable impact in healthcare delivery while working with sophisticated institutional buyers.

Responsibilities

• Own the full sales cycle for a named book of private multiemployer Taft-Hartley funds and public-sector union funds (10,000 to 100,000 participants)
• Sell directly to boards of trustees by building fund office relationships and navigating joint labor-management board dynamics
• Win support from both labor and management sides in trustee environments
• Maintain current market knowledge and competitive intelligence to effectively communicate value propositions
• Develop strategic relationships with fund professionals including administrators, actuaries, legal counsel, and consultants
• Work the conference circuit (IFEBP and similar) to build and maintain industry presence
• Prepare and track against sales quotas with disciplined prospecting and pipeline management

What We're Looking For

• Bachelor's degree required
• 7+ years of sales experience in health benefits (medical, ancillary, or vendor solutions) selling via brokers, consultants, and insurers
• 5+ years selling into labor/Taft-Hartley funds strongly preferred, with demonstrated fluency in joint boards, collective bargaining linkage, and fund professional ecosystems
• Existing, reference-checkable relationships with trustees, fund administrators, and labor consultants
• Credibility and comfort presenting to union leadership
• Data literacy with ability to translate complex datasets into actionable insights
• Proven experience developing sales processes including playbooks, KPIs, and collateral
• Mission-driven mindset with accountability to measurable outcomes
• Comfort using AI tools as part of your sales approach

How We Work With You

When you apply through Get A Job.ai, our talent team will conduct an initial screening to understand your background and interest in this role. If there's a strong fit, we'll submit your profile to our client for consideration. Please do not contact the employer directly—all communication and coordination will flow through our recruiting team to ensure the best candidate experience.

This is a remote position with occasional travel to the client's headquarters in New York City. Please note that visa sponsorship is not available for this role.

Pay

Our client has indicated a target total compensation range of $425,000 - $475,000 (inclusive of base salary plus bonus), depending on qualifications and experience. The role also includes equity participation, flexible PTO, comprehensive medical/dental/vision coverage, 401(k) with company match, and additional benefits.

Get A Job.ai is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees and candidates.