Director of Sales (Health Systems)

Description Join Us at TailorMed – Transforming Healthcare Affordability Awarded Best in Class in Health Equity 2025 At TailorMed, we’re on a mission to eliminate barriers across the entire medication journey—from affordability to access and adherence. As a pioneering force in healthcare, we’re building a new category that transforms how patients, providers, pharmacies, life sciences, and payers collaborate to ensure every patient receives the treatment they need without delay. TailorMed is the medication success platform removing every barrier across the patient journey, from access and affordability through adherence and ongoing care. Through a connected network spanning 945+ hospitals, 4,700+ clinics, 3,100+ pharmacies, 100+ life sciences programs, and 6,000+ support programs, TailorMed has supported over 75 million patients and secured more than $7.4 billion in financial assistance since 2020. TailorMed's platform, including TailorMed Core, TailorMed Connect, TailorMed Complete, TailorMed Amplify, and TailorMed Alliance, connects patients, providers, pharmacies, and life sciences companies through one coordinated network designed to reach every patient at every step of their medication journey. Learn more at tailormed.co Are you a proven sales leader with a track record in enterprise healthcare SaaS sales? We’re seeking a Director of Sales to drive growth and expand our impact across health systems, IDNs, oncology networks, and specialty pharmacies. In this strategic role, you’ll own a portfolio of enterprise accounts while relentlessly pursuing new business opportunities in the digital health, patient access, and affordability solutions space. You’ll thrive here if you’re energized by purpose-driven work, skilled at navigating complex healthcare organizations, and motivated by the challenge of exceeding quotas in long-cycle, high-value sales environments. Join our fast-growing team and help shape the future of patient affordability in healthcare. Responsibilities: Identify and cultivate new sales opportunities and convert relationships into long-term partnerships Develop comprehensive business plans to achieve and exceed sales targets and quotas Engage clients to understand project scope, budgets, and timelines Own the entire sales cycle, from prospecting and lead generation through closing the deal Lead negotiations and oversee contracts while maintaining accurate sales records Partner with executives to align on client objectives and deliver measurable results Strengthen customer loyalty and build lasting trust with exceptional post-sale support and follow-through Communicate proactively and consistently with clients to anticipate and meet their evolving needs Requirements: Demonstrated success in enterprise-level, B2B healthcare SaaS sales, preferably in areas such as patient support services, specialty pharmacy, care coordination, or financial assistance platforms—where navigating clinical and administrative workflows is essential Proven track record selling into complex healthcare organizations, including health systems, IDNs, oncology departments, specialty pharmacies, and/or community oncology centers, with experience managing long sales cycles and engaging cross-functional stakeholders Understanding of the patient affordability landscape, including exposure to copay assistance programs, foundation support, free drug programs, or reimbursement navigation—ideally through direct collaboration with access, financial navigation, or specialty pharmacy teams Exceptional relationship-building, communication, and presentation skills Ability and desire to target and develop cold leads and build pipeline Knowledge of industry-relevant market research, sales, and negotiating principles Strong planning, closing, and multitasking skills Ability to learn and adapt quickly Enthusiastic with a positive attitude, resilience, and perseverance Willing to travel 30-50% of the time What We Offer Competitive salary + equity Premium medical, dental, and vision insurance plans, a wide range of voluntary and supplemental benefits, and 24/7 benefits access and support - all effective from your first day of work 401(k) plan with a 4% employer match Paid holidays, vacation, and sick leave Six weeks of paid parental leave Company-paid life insurance New MacBook, plus all of the equipment and technology you’ll need to be successful in your role The opportunity to help shape the future of healthcare TailorMed is proud to be an equal opportunity employer. TailorMed prohibits discrimination and harassment of any type and affords equal employment opportunities to employees and applicants without regard to race, color, religion, sex, sexual orientation, gender identity or expression, pregnancy, age, national origin, disability status, genetic information, protected veteran status, or any other characteristic protected by law. Due to the sensitive nature of the data that TailorMed handles, finalist candidates must complete a successful background and reference check. At this time, TailorMed is unable to provide sponsorship for employment. In order to be considered for employment, applicants must be currently legally authorized to work in the United States and not require future sponsorship in order to continue working in the United States.