Director of Sales (Health Systems)

About The Position

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.

About the Role:

We’re looking for a high-performing Director of Sales to drive growth and expand our impact across the healthcare and provider landscape. In this strategic role, you’ll own a portfolio of accounts while relentlessly pursuing new business opportunities. Your ability to build trust with stakeholders—ranging from clinical users to the C-suite—will be key to your success.

We’re seeking a proven sales leader with experience selling technology solutions in complex healthcare environments. If you’re energized by purpose-driven work, thrive in fast-moving startups, and have a strong track record of exceeding sales targets, we’d love to hear from you. This is your chance to join a passionate, forward-thinking team—and help shape the future of patient affordability in healthcare.

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

• 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 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
• 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.