Sr. Regional Sales Director, Labor Sales

This position is posted by Jobgether on behalf of a partner company. We are currently looking for a Sr. Regional Sales Director, Labor Sales in the United States.

This senior sales leadership role is focused on driving growth across complex labor and multi-employer healthcare markets, with a strong emphasis on unionized and Taft-Hartley benefit structures. You will be responsible for identifying, developing, and closing large-scale opportunities that help organizations reduce healthcare costs while improving outcomes across chronic care, mental health, and virtual health programs. The role requires deep expertise in navigating multi-stakeholder environments involving unions, trustees, benefits administrators, and healthcare partners. You will operate in a highly strategic, consultative sales capacity, combining relationship-building, market insight, and disciplined execution. This is a high-impact, remote-based role suited for a sales leader who thrives in complex healthcare ecosystems and is motivated by mission-driven outcomes.

• Drive revenue growth across employer and labor union (Taft-Hartley) markets by identifying and closing large-scale healthcare solution opportunities.
• Build and maintain strong relationships with HR leaders, benefits administrators, union representatives, and trust fund stakeholders.
• Develop strategic account plans, forecasting models, and operating cadences to guide execution and performance tracking.
• Prospect and expand market share by identifying new opportunities within assigned regions and accounts.
• Lead complex sales cycles involving multiple stakeholders, including boards of trustees, unions, consultants, and third-party administrators.
• Translate customer needs and market dynamics into tailored healthcare solutions across chronic care, mental health, and virtual health offerings.
• Collaborate with sales leadership to define and execute mid-market and enterprise growth strategies.
• Ensure high levels of customer satisfaction through proactive issue resolution and account management.
• Support onboarding and mentorship of new sales team members as needed.
• Maintain strong awareness of industry trends, payer/provider ecosystems, and competitive dynamics.
• Travel as required (up to 50%) to support client engagement and relationship development.

Requirements:

• Bachelor’s degree in Business, Marketing, Communications, Engineering, or related field.
• 3+ years of experience working with Taft-Hartley funds, labor unions, or multi-employer healthcare benefit structures.
• Proven success in complex, consultative sales within regulated healthcare or medical product environments.
• Strong understanding of union governance models, collectively bargained benefits, and multi-stakeholder decision-making processes.
• Demonstrated ability to manage and grow strategic accounts in highly complex buying environments.
• Excellent communication, presentation, and relationship-building skills across executive and trustee-level audiences.
• Strong analytical and strategic thinking skills with the ability to build structured account plans and forecasts.
• Experience navigating healthcare ecosystems including brokers, consultants, TPAs, and payers is highly preferred.
• Established network within labor union or Taft-Hartley markets is a strong advantage.
• Ability to influence, negotiate, and build trust across diverse stakeholder groups.
• Self-driven, results-oriented mindset with strong organizational and execution capabilities.

Benefits:

• Competitive base salary ranging from $150,000 to $160,000 USD
• Performance-based bonus eligibility
• Comprehensive benefits package including medical, dental, and vision coverage
• Paid time off, flexible vacation policy, and 80 hours of paid sick and caregiver leave annually
• Remote work flexibility across the United States (travel up to 50% as required)
• Inclusive and mission-driven culture focused on improving access to healthcare
• Career development opportunities within a high-growth, innovation-focused organization
• Employee wellbeing and family-centered support programs
• Exposure to complex, high-impact healthcare transformation initiatives.