Director of Sales, Health Systems

100% remote & full-time | South/Midwest (TX, Southeast) preferred | Individual Contributor Our client TailorMed has connected patients across 945+ hospitals to over $7.4 billion in financial assistance since 2020 — and they're just getting started. They're seeking a proven enterprise healthcare SaaS sales leader to drive growth across health systems, IDNs, oncology networks, and specialty pharmacies. You'll own strategic accounts, develop new business in the patient access and affordability space, and thrive in a high-impact role selling complex solutions into healthcare organizations. This is a true enterprise role. You'll own a territory, build your own pipeline, navigate complex health system organizations, and close long-cycle deals — and you'll do it with full conviction because the ROI story is real and the mission is genuine. The fit: 5+ years in enterprise B2B healthcare SaaS — specifically into health systems, IDNs, or oncology networks Comfortable calling on Chief Pharmacy Officers, VP Revenue Cycle, and CFO-level stakeholders Can hunt, not just farm — BDR support is coming but you can't wait for it Comfortable with 30–50% travel Startup-minded: energized by building, not by process The deal: ~$300–$350K OTE (50% base, 50% commission, uncapped) Fully remote | territory: South/Midwest (TX, Southeast) Mentorship from a VP who's been there, done that, and genuinely invests in her team Premium medical, dental, and vision insurance — effective day one 401(k) with 4% employer match Paid holidays, vacation, and sick leave Six weeks paid parental leave Company-paid life insurance All the equipment and technology you need to be successful Widger Talent LLC is a boutique recruiting agency. We represent TailorMed directly but non-exclusively for this search.