Director of Sales – Health Systems

TailorMed

full-time

Posted on: 3/31/2026

Location Type: Remote

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About the role

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

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

Benefits

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

Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools

B2B salesSaaS salessales cycle managementnegotiationpipeline developmentmarket researchsales principlesclosing skillsmultitasking

Soft Skills

relationship-buildingcommunication skillspresentation skillsplanningadaptabilitypositive attituderesilienceperseverance