Description
We are seeking an entrepreneurial, highly autonomous Director of Healthcare Sales to serve as our founding sales leader. This is a rare opportunity for an elite enterprise healthcare sales professional who thrives in a high-ownership, builder environment and wants a direct path to executive leadership.
Initially, you will operate as a high-impact individual contributor—owning the full enterprise sales cycle end-to-end and directly closing net-new business with hospitals and health systems. At the outset, you will be provided sales leads generated from previous conferences and there will not be a marketing department feeding you inbound leads; instead, you will generate your own pipeline using existing relationships deep account targeting, and fully funded attendance at major national healthcare conferences.
While you will have full access to internal resources and technical support for sales calls and deep-dive demonstrations early on, you will be expected to rapidly build proficiency in CareWare and the broader competitive landscape.
The Growth Path: As you create and validate the sales playbook and scale CareWare’s enterprise footprint, you will have the mandate and support transition into a leadership role—building, recruiting, and managing our sales team from the ground up.
Mandatory Requirement
Candidates must have a minimum of 4+ years of direct, quota-carrying experience selling enterprise software (SaaS) into acute care hospitals and health systems. Examples include learning management systems, credential management software, analytics software, EHR, Applicantswithout a verifiable background in healthcare technology sales will not be considered.
Key Responsibilities
- Own the Enterprise Revenue Engine: Independently drive the full enterprise sales cycle from cold outbound prospecting and initial discovery to technical solution demonstrations, RFP navigation, and contract execution.
- Master the Product & Market: Take proactive ownership of becoming deeply proficient in CareWare’s software offering, core value propositions, and competitive positioning.
- Leverage Internal Expertise: Strategically utilize internal resources, technical specialists, and team members to support and validate early-stage sales calls, architecture reviews, and product demonstrations while building your own technical fluency.
- Generate Pipeline Without Inbound Support: Build and manage a strategic outbound pipeline using account-based prospecting methods. You must be comfortable working as a self-sufficient hunter without an active lead-generation or inbound marketing engine.
- Maximize National Conference ROI: Represent Care Systems as the primary face of the company at key national healthcare conferences. Independently manage pre-conference outreach, execute high-impact on-site networking, and handle rigorous post-event deal follow-up.
- Navigate Complex Buying Committees: Build champions and multi-thread effectively across clinical, operational, and financial hospital executives (e.g., Chief Nursing Officers, COOs, CIOs, and VPs of Workforce/Operations).
- Author the Sales Playbook: Document successful strategies, build out repeatable discovery frameworks, and establish scalable workflows that will serve as the foundation for future sales hires.
- Prepare for Team Expansion: Act as a strategic advisor to executive leadership on pricing, product-market fit, and market trends, laying the organizational groundwork to recruit and manage a team of AEs and SDRs down the line.
Minimum Qualifications
- Experience: 6+ years of total B2B SaaS sales experience, with at least 4+ years specifically selling software into hospital networks or acute care facilities.
- Builder Mindset: Proven experience working as a founding salesperson, early-stage hire, or highly independent remote rep who successfully built a territory from scratch.
- Track Record: Documented history of consistently meeting or exceeding an enterprise quota (e.g., $1M+ annual target) with average contract values exceeding $100,000.
- Healthcare Domain Expertise: Deep familiarity with hospital purchasing dynamics, operational metrics, and multi-month procurement and legal cycles.
- Executive Presence: Exceptional presentation and value-based selling skills, with the ability to confidently pitch complex software solutions to hospital C-suite executives.
- Travel: Willingness to travel as needed to achieve sales targets
Preferred Qualifications (Premium Compensation Tier)
- Direct experience selling workforce management, scheduling, time and attendance, or clinical HRIS solutions to healthcare networks (Experience with specialized provider or staff scheduling solutions qualify for a premium starting base pay).
- An active, warm network of hospital administrative and nursing leadership (CNOs, VPs of Nursing, Chief HR Officers).
- Prior experience as a team lead, sales mentor, or player-coach with a desire to transition into formal sales management.
Target Base Pay: $130,000+ (Base pay is negotiable based on experience; a premium base salary tier is explicitly reserved for candidates with direct scheduling software experience. 50/50 uncapped commission structure
Pay: $130,000.00 - $300,000.00 per year
Benefits:
- Health insurance
- Paid time off
Application Question(s):
- Do you have experience selling to hospitals or health systems?
Work Location: Remote
