TrueLearn is seeking an senior level Account Executive, Enterprise Sales & Strategic Partnerships to lead high-value, complex enterprise sales within the private-sector medical workforce management market. This role is designed for an experienced enterprise seller who excels at navigating long, consultative sales cycles, influencing senior decision-makers, and closing large, multi-year agreements with commercially oriented healthcare organizations.

The Director will own the enterprise sales motion end-to-end, from market strategy and executive engagement through negotiation, contracting, and long-term account expansion. This position will play a critical role in shaping TrueLearn’s enterprise go-to-market strategy and will evolve into a people-management role as enterprise revenue scales.

• Own and execute the enterprise sales strategy targeting private-sector healthcare and medical workforce organizations.

• Drive large-deal, multi-year enterprise contracts that generate meaningful ARR and long-term customer value.

• Manage complex, consultative sales cycles involving multiple stakeholders, cross-functional buying committees, and executive leadership.

• Build and maintain trusted relationships with C-suite executives, operations leaders, HR and workforce leaders, clinical leadership, and commercial decision-makers.

• Position TrueLearn as a strategic partner aligned to workforce performance, talent development, and operational outcomes.

• Expand enterprise accounts through land-and-expand strategies, upsell, and cross-sell initiatives.

• Help define and refine the enterprise GTM strategy for TrueLearn’s workforce-focused solutions.

• Identify, structure, and execute strategic partnerships that unlock enterprise distribution, bundled offerings, or new commercial channels.

• Collaborate closely with marketing, product, and leadership teams to ensure enterprise customer needs shape positioning and roadmap priorities.

• Own the full enterprise sales lifecycle: prospecting, discovery, solution design, executive presentations, pricing, negotiation, and close.

• Lead enterprise-level proposals, proofs of concept, and complex contract negotiations.

• Maintain accurate pipeline management, forecasting, and CRM reporting.

• Stay current on trends in medical workforce management, staffing, credentialing, professional development, and healthcare operations.

• Monitor competitive dynamics and buyer behavior to continuously optimize enterprise sales strategy.

• 8+ years of B2B sales experience, with a strong emphasis on enterprise-level, complex sales.

• Proven success closing large, multi-year deals with long sales cycles and sophisticated buyers.

• Experience selling into private-sector healthcare organizations, workforce management platforms, staffing firms, MSOs, or other commercial healthcare entities.

• Demonstrated ability to navigate multi-stakeholder buying environments and sell at the executive level.

• Strong contract negotiation and enterprise pricing experience.

• Proficiency with CRM platforms (Salesforce, HubSpot, or equivalent).

• Exceptional executive communication, presentation, and negotiation skills.

• Strategic, self-directed, and comfortable operating in a high-growth environment.