Head of Sales

This is a fully remote position, open to applicants in United States.

📋 Description

• Take ownership of and implement the comprehensive sales strategy across all market segments, including employer, health plan, broker/small group, client expansion, and labor.

• Define clear priorities, target segments, and operational mechanisms to foster sustainable revenue growth and expand market share.

• Ensure alignment between corporate strategy, go-to-market initiatives, and field execution.

• Act as a senior advisor to the executive team regarding market dynamics, competitive trends, and opportunities for growth.

• Lead and mentor senior sales leaders (VP/RVP level), ensuring clarity of roles, accountability, and consistent execution among teams.

• Drive pipeline generation, deal progression, forecasting discipline, and booking performance across various sales strategies.

• Balance strategies for acquiring new logos, expanding existing accounts, and retaining clients across the portfolio.

• Advocate for disciplined sales processes, metrics, and performance management to enhance predictability and outcomes.

• Build, lead, and maintain a high-performing, value-driven sales organization.

• Coach and develop leaders to operate at an enterprise scale—crafting strategy, managing complexity, and leading through influence.

• Foster a robust culture of accountability, collaboration, and continuous improvement.

• Develop and sustain executive-level relationships with key customers, benefit leaders, consultants, and strategic partners.

⛳️ Requirements

• A bachelor’s degree is required; an MBA or advanced degree is preferred.

• Over 12 years of progressive sales leadership experience, with a proven track record of leading large, multi-layered sales organizations.

• Experience in complex B2B sales environments; healthcare, health plan, employer, or regulated industry experience is highly preferred.

• Familiarity with various go-to-market motions (e.g., employer, payer, partners, consultants, labor, or enterprise clients).

• Demonstrated capability to lead senior leaders, manage through influence, and ensure alignment across distributed teams.

• Proven history of driving revenue growth, building scalable operating models, and cultivating high-impact leaders.

• Strong executive presence, excellent communication skills, and credibility with both internal and external stakeholders.

🏝️ Benefits

• Flexible Vacation Policy

• 80 hours of Paid Sick, Safe, and Caregiver Leave annually