Director of Sales (Health Systems)

TailorMed

$150K — $180K *
Healthcare
5 - 7 years of experience
Job Overview by Ladders

Qualifications

  • 5-7 years of enterprise-level, B2B healthcare SaaS sales experience
  • Proven success selling to complex healthcare organizations
  • Familiarity with the patient affordability landscape
  • Outstanding relationship-building and communication skills
  • Ability to target and develop cold leads
  • Strong multitasking and closing skills
  • Willingness to travel 30-50% of the time

Responsibilities

  • Identify and convert new sales opportunities into long-term partnerships
  • Develop business plans to achieve and exceed sales targets
  • Engage clients to define project scope, budgets, and timelines
  • Own the entire sales cycle from lead generation to closing
  • Negotiate and oversee contracts while maintaining sales records
  • Collaborate with executives on client objectives for measurable outcomes
  • Enhance customer loyalty through exceptional post-sale support

Benefits

  • Premium medical, dental, and vision insurance effective from day one
  • 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 and necessary equipment for success
  • Opportunity to impact the future of healthcare
Full Job Description
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

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