Director of Sales (Health Systems)

Join Us at TailorMed – Transforming Healthcare Affordability

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.

Our enterprise solution streamlines the full lifecycle of patient support programs, reducing the cost of care and driving better outcomes. With the nation's largest Affordability Network—deployed across 800+ hospitals, 1,300 clinics, and 650 pharmacies—we’re reshaping healthcare with innovative automation and industry-leading partnerships.

If you’re passionate about making healthcare more accessible and impactful, we’d love to have you on our team. Join us and help redefine what’s possible. Learn more at tailormed.co.

The Director of Sales will build and oversee a portfolio of accounts, ensuring high levels of client satisfaction and retention while actively pursuing and securing new business opportunities. The ideal candidate will have a proven history of generating new business and achieving sales targets, with a strong ability to excel in outbound prospecting within a competitive landscape.

Success in this role requires experience selling technology solutions within complex healthcare settings, where you have navigated multiple stakeholders from end users to C-suite executives. At TailorMed, you will be expected to be relationship-driven and revenue-focused. A self-starter with meticulous attention to detail, you should excel in a dynamic, fast-paced start-up environment.

Responsibilities:

• Develop comprehensive business plans to achieve sales targets and quotas
• Engage with clients to understand project scope, budgets, and timelines
• Oversee the complete sales cycle, from lead generation to deal closure
• Identify and cultivate new sales opportunities through networking and converting relationships into long-term partnerships
• Negotiate agreements and maintain detailed sales records
• Collaborate with executives to align on clients’ project objectives and track progress
• Provide professional and exceptional after-sales support to enhance the customers’ dedication
• Maintain regular communication with clients to anticipate and meet their needs
  
  

Requirements:

• Proven success in an enterprise-level, B2B healthcare SaaS sales role, with experience in verticals such as healthcare IT, pharmacy solutions, revenue cycle, EMRs, etc.
• Experience selling to health systems, IDNs, oncology departments, and community oncology centers
• Exceptional relationship-building, communication, and presentation skills
• Ability and desire to target and develop cold leads and build pipeline
• Skilled in managing deals with multiple stakeholders in large enterprises
• Knowledge of industry-relevant market research, sales, and negotiating principles
• Experience with CRM software - we’re using Salesforce
• Strong planning, closing, and multitasking skills
• Ability to learn and adapt quickly
• Experience in budget management
• Familiarity with sales techniques and account management
• 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.