Director of Sales - MDLive - Remote

Position Description
As the Director of Sales, you will be responsible for driving new logo acquisition and revenue growth across health plans, employers, TPAs, consultants, and health systems.

This is a true hunter role focused on identifying, developing, and closing strategic enterprise opportunities within a complex healthcare landscape.

The successful candidate will demonstrate a proven track record of exceeding sales quotas through proactive prospecting, executive relationship development, and disciplined execution of complex, multi-stakeholder sales processes.

This individual must be comfortable getting into the details of sophisticated healthcare benefit and virtual care solutions, working closely with internal business partners and external stakeholders to design solutions that meet client needs.

This position owns the entire customer acquisition lifecycle, from prospecting and opportunity development through contracting, implementation support, and formal transition to Client Success. Success requires close collaboration with Product, Clinical, Network, Operations, Finance, Legal, Implementation, Marketing, and Client Success teams to develop customized solutions and navigate complex organizational structures.

The ideal candidate is a highly motivated self-starter who thrives in a fast-paced environment, learns quickly, maintains a positive and team-oriented mindset, and has the persistence and resilience necessary to win highly competitive enterprise opportunities.

Essential Job Functions

• Drive net-new logo acquisition within an assigned territory through strategic prospecting, executive relationship development, and disciplined pipeline management to meet or exceed annual revenue quotas.
• Develop and execute territory and account strategies, buyer engagement plans, and opportunity-specific sales motions that create a clear path to close.
• Lead complex, consultative sales processes involving clinical, operational, financial, technology, procurement, legal, and executive stakeholders.
• Develop a deep understanding of prospect benefit strategies, plan designs, funding arrangements, member engagement challenges, and total cost of care objectives to position MDLive solutions effectively.
• Build and maintain executive-level relationships with health plans, employers, consultants, TPAs, health systems, brokers, and strategic partners.
• Partner closely with Product, Clinical, Network, Operations, Finance, Legal, Implementation, Marketing, and Client Success teams to develop customized solutions and ensure successful execution throughout the customer lifecycle.
• Coordinate and lead internal deal teams, driving alignment, accountability, and timely execution from opportunity development through contracting, implementation readiness, and transition to Client Success.
• Navigate complex organizational structures, procurement processes, stakeholder dynamics, and decision-making frameworks to advance opportunities and remove barriers to close.
• Maintain accurate pipeline, forecasting, and opportunity management within Salesforce while providing visibility into deal progress, risks, and growth opportunities.
• Develop pricing strategies, financial proposals, and business cases that align customer needs with MDLive's growth objectives.
• Monitor competitive activity, market trends, virtual care innovations, and healthcare benefit developments to refine positioning and strengthen sales strategies.
• Provide market feedback and customer insights to influence product development, pricing strategies, and go-to-market initiatives.
• Manage and develop assigned direct reports, including coaching, performance management, and professional development.
• Other duties as assigned.

Required Knowledge/Skills/Abilities

• Demonstrated success meeting and exceeding enterprise sales quotas in healthcare, digital health, benefits, or virtual care markets.
• Proven track record of acquiring net-new logos and building pipeline through proactive business development efforts.
• Deep understanding of healthcare benefits, plan design, funding arrangements, and employer and health plan buying processes.
• Strong knowledge of the virtual care, digital health, and healthcare benefits ecosystem.
• Ability to manage complex, detail-oriented sales cycles involving multiple stakeholders and extended purchasing timelines.
• Experience collaborating with cross-functional teams to develop customized client solutions and navigate operational, clinical, technical, and contractual requirements.
• Established executive-level relationships within health plans, employers, consultants, TPAs, and healthcare organizations.
• Strong executive presence with demonstrated success engaging C-suite decision makers.
• Exceptional organizational, analytical, and project management skills with the ability to manage multiple priorities simultaneously.
• Ability to rapidly learn new products, market dynamics, and healthcare trends.
• Positive, collaborative, team-first mindset with a strong work ethic and high degree of accountability.
• Strong negotiation, communication, presentation, and relationship management skills.
• Experience utilizing Salesforce and related sales technologies to maintain accurate forecasting and pipeline visibility.
• Experience in utilizing AI tools on a day-to-day basis to support workflows and to create efficiencies.
• Ability to work effectively across complex organizations and influence outcomes without direct authority.

Education and Experience

• Bachelor's degree preferred.
• 10+ years of enterprise healthcare sales experience, preferably within virtual care, digital health, health plans, healthcare benefits, or employer solutions.
• Demonstrated success selling to health plans, large employers, consultants, TPAs, and healthcare organizations.
• Proven history of achieving or exceeding annual sales quotas and revenue targets.
• Experience selling solutions that require coordination across clinical, operational, financial, technology, and executive stakeholder groups.
• Experience with provider network strategy or network contracting is strongly preferred.
• Experience managing opportunities through implementation and client transition processes preferred.

Travel Requirements

Up to 40%

If you will be working at home occasionally or permanently, the internet connection must be obtained through a cable broadband or fiber optic internet service provider with speeds of at least 10Mbps download/5Mbps upload.

About Evernorth Health Services

Evernorth Health Services, a division of The Cigna Group, creates pharmacy, care and benefit solutions to improve health and increase vitality. We relentlessly innovate to make the prediction, prevention and treatment of illness and disease more accessible to millions of people. Join us in driving growth and improving lives.

Qualified applicants will be considered without regard to race, color, age, disability, sex, childbirth (including pregnancy) or related medical conditions including but not limited to lactation, sexual orientation, gender identity or expression, veteran or military status, religion, national origin, ancestry, marital or familial status, genetic information, status with regard to public assistance, citizenship status or any other characteristic protected by applicable equal employment opportunity laws.

If you need a reasonable accommodation to complete the online application process, please email View email address on click.appcast.io for assistance. Please note that this email inbox is dedicated to accommodation requests only and cannot provide application updates or accept resumes.

The Cigna Group has a tobacco-free policy and reserves the right not to hire tobacco/nicotine users in states where that is legally permissible. Candidates in such states who use tobacco/nicotine will not be considered for employment unless they enter a qualifying smoking cessation program prior to the start of their employment. These states include: Alabama, Alaska, Arizona, Arkansas, Delaware, Florida, Georgia, Hawaii, Idaho, Iowa, Kansas, Maryland, Massachusetts, Michigan, Nebraska, Ohio, Pennsylvania, Texas, Utah, Vermont, and Washington State.

Qualified applicants with criminal histories will be considered for employment in a manner consistent with all federal, state and local ordinances.