Head of Sales

Teladoc Health•McCullom Lake, IL

10d•$270,000 - $310,000

About The Position

Join the team leading the next evolution of virtual care. At Teladoc Health, you are empowered to bring your true self to work while helping millions of people live their healthiest lives. Here you will be part of a high-performance culture where colleagues embrace challenges, drive transformative solutions, and create opportunities for growth. Together, we’re transforming how better health happens. Summary of Position The Head of Sales is a senior enterprise leader responsible for setting and executing Teladoc Health’s overall sales strategy across all commercial growth segments. This role provides unified leadership across employer, health plan, broker/small group, client expansion, and labor sales, ensuring coherence, accountability, and scalable execution in a complex, regulated healthcare environment. This leader is first and foremost a people and business leader—not a subject‑matter expert. Success in this role requires exceptional leadership capability, strong commercial judgment, and the ability to align diverse sales motions under a common strategy, operating cadence, and culture of performance. The Head of Sales partners closely with Product, Clinical, Finance, Marketing, Strategy, and Operations to translate market insight into executable growth plans and to serve as the executive voice of the market to company leadership.

Requirements

Bachelor’s degree required; MBA or advanced degree preferred.
12+ years of progressive sales leadership experience, with demonstrated success leading large, multi‑layered sales organizations.
Experience across complex B2B sales environments; healthcare, health plan, employer, or regulated industry experience strongly preferred.
Exposure to multiple go‑to‑market motions (e.g., employer, payer, partners, consultants, labor, or enterprise clients).
Proven ability to lead senior leaders, manage through influence, and align execution across distributed teams.
Track record of delivering revenue growth, building scalable operating models, and developing high‑impact leaders.
Strong executive presence, communication skills, and credibility with both internal and external stakeholders.
Applicants must be currently authorized to work in the United States without the need for visa sponsorship now or in the future.

Responsibilities

Own and execute the end‑to‑end sales strategy across all market segments, including employer, health plan, broker/small group, client expansion, and labor.
Establish clear priorities, target segments, and operating mechanisms to drive sustainable revenue growth and market share expansion.
Ensure alignment between corporate strategy, go‑to‑market plans, and field execution.
Serve as a senior advisor to the executive team on market dynamics, competitive trends, and growth opportunities.
Lead and develop senior sales leaders (VP/RVP level), ensuring clarity of roles, accountability, and consistent execution across teams.
Drive pipeline generation, deal progression, forecasting discipline, and booking performance across diverse sales motions.
Balance new logo acquisition, expansion, and retention strategies across the portfolio.
Champion disciplined sales processes, metrics, and performance management to improve predictability and results.
Build, lead, and retain a high‑performing, value-driven sales organization.
Coach and develop leaders to operate at enterprise scale—setting strategy, managing complexity, and leading through influence.
Establish a strong culture of accountability, collaboration, and continuous improvement.
Ensure succession planning and leadership bench strength across the commercial organization.
Partner closely with Product, Clinical, Finance, Marketing, Operations, Strategy, and HR to Shape offerings and pricing strategies, Improve sales enablement and productivity, Inform roadmap and investment decisions with real‑time market insight, Influence without authority in a matrixed environment, ensuring alignment and speed.
Build and maintain executive‑level relationships with key customers, benefit leaders, consultants, and strategic partners.
Represent Teladoc Health externally in high‑impact client engagements and industry forums as needed.
Ensure the sales organization delivers a high‑quality, consistent client experience that reflects Teladoc Health’s mission and brand.