Enterprise Sales Executive

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. Our connected network spans 945+ hospitals, 4,700+ clinics, 3,100+ pharmacies, 100+ life sciences programs with a reach of 75 million patients and has secured more than $7.4 billion in financial assistance since 2020 tapping into an asset of 6000+ support programs.

Learn more at tailormed.com

Are you an emerging sales leader with experience in healthcare SaaS and a strong desire to grow into a strategic enterprise role? We’re seeking an Enterprise Sales Executive to help drive growth and expand our impact across health systems, IDNs, oncology networks, and specialty pharmacies. In this role, you’ll manage a portfolio of enterprise accounts while building 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, eager to deepen your experience navigating complex healthcare organizations, and motivated to grow your skills 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 business plans to achieve and exceed sales targets and quotas
• Engage clients to understand project scope, budgets, and timelines
• Own the full sales cycle, with support and collaboration as needed, from prospecting through closing
• Participate in negotiations and support contract execution while maintaining accurate sales records
• Partner closely with internal stakeholders, including senior team members, to align on client objectives and deliver results
• Build strong client relationships and support post-sale success and follow-through
• Communicate proactively with clients to anticipate and meet evolving needs

Requirements:

Experience in B2B healthcare SaaS sales, with exposure to enterprise or complex sales environments

• Some experience selling into healthcare organizations such as health systems, IDNs, oncology departments, or specialty pharmacies, with a desire to deepen this expertise
• Familiarity with the patient affordability landscape (e.g., copay assistance, foundation support, reimbursement navigation) is a plus, but not required
• Strong relationship-building, communication, and presentation skills
• Demonstrated ability or strong interest in building pipeline, including sourcing and developing new opportunities
• Solid foundation in sales and negotiation principles, with a willingness to learn and grow
• Strong planning, organization, and multitasking skills
• Ability to learn quickly, take feedback, and adapt in a fast-paced environment
• High motivation, resilience, and a growth mindset
• Willingness to travel 30–50% of the time

• 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.