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 buil