Enterprise Healthcare Sales Executive
Role Overview
This is a senior-level Enterprise Healthcare Sales Executive role on the B2B sales team, responsible for managing the full sales cycle from prospecting to closing deals with large healthcare systems and hospital networks. The role involves building relationships with HR, L&D, and operational leaders, navigating multi-stakeholder buying committees, and positioning Stepful as a strategic partner to address workforce challenges. The hire will have a significant impact by driving revenue growth and expanding Stepful's footprint in the healthcare ecosystem.
Perks & Benefits
The role is fully remote with 15 work-from-anywhere days, an open vacation policy including 15 days PTO annually, and 10 public holidays observed for 2025. Benefits include a meaningful equity stake, subsidized medical, dental, and vision insurance, 401(k), FSA, HSA, commuter benefits, and a learning stipend. The culture emphasizes a fast-paced, mission-driven environment with core values like care first, learning quickly, building together, and owning it, supporting career growth in a startup setting.
Full Job Description
About Stepful:
Stepful is reimagining allied healthcare training by offering affordable, online, instructor-led, and AI-supported programs that help learners—especially those from underserved communities—launch high-demand healthcare careers.
In addition to our direct-to-consumer training, Stepful partners with leading healthcare institutions to build talent pipelines and address the growing shortage of allied health workers. Our graduates, including Medical Assistants, Pharmacy Technicians and more, go on to work at major employers like CVS, NY-Presbyterian, and Walgreens.
Stepful is backed by Y Combinator, Reach Capital, and AlleyCorp, with a recent $31.5M Series B led by Oak HC/FT. Additionally, we were named the #1 EdTech company in the U.S. by TIME for 2025 and to GSV's 150 Most Transformational Growth Companies in Digital Learning.
We’re unlocking the full potential of the global workforce—improving access to quality healthcare for everyone, everywhere.
Our values:
We credit much of our success to our exceptional team. We’re looking for mission-driven individuals who thrive in fast-paced, sometimes ambiguous environments, and embody our four core values:
Care first: We do whatever it takes for our students to succeed.
Learn quickly: We test, learn with data, and iterate.
Build together: We win when we rely on each other.
Own it: We show up, take initiative, and show pride.
The opportunity:
We’re looking for a driven, enterprise-minded seller to join our growing B2B sales team. In this role, you’ll lead new business development with large healthcare systems and hospital networks—building relationships with HR, L&D, and operational leaders, uncovering complex workforce challenges, and positioning Stepful as a strategic partner in developing and retaining clinical talent.
This is a quota-carrying role with full ownership of the sales cycle, from outbound prospecting through close. You’ll navigate multi-stakeholder buying committees, partner closely with sales leadership on deal strategy, and help expand Stepful’s footprint across the healthcare ecosystem.
This role reports to the VP of Sales.
What you'll do:
Manage the full sales cycle from outreach to close, with a focus on healthcare providers and systems
Build and execute a strategic plan to achieve and exceed revenue targets
Cultivate a strong sales pipeline through a combination of outbound prospecting and inbound lead conversion
Lead consultative conversations with VP- and C-level executives, helping them solve workforce and capacity challenges with Stepful programs
Create tailored presentations, proposals, and supporting sales materials to guide prospects through the buying process
Collaborate cross-functionally with Customer Success, Program Operations, Solutions Architects, and RevOps to ensure a seamless handoff and long-term customer success
Represent Stepful at conferences, onsite meetings, and local events to deepen engagement with customers and prospects
What you'll bring:
5+ years of sales experience, preferably in healthcare, education, or workforce development
Experience closing complex deals ($100K–$1M+) with senior stakeholders
Familiarity with the provider-side healthcare industry and selling into talent acquisition, HR, or operations teams
A strong ability to build rapport, tell compelling stories, and drive urgency in the sales process
A data-driven, self-starter mindset with a bias toward execution
Comfort navigating fast-paced, startup environments with evolving processes
Bonus points if:
You've sold directly to healthcare systems or hospitals
You have experience selling into healthcare-focused HR and talent acquisition teams
Interview Process:
Intro Call with Talent Team
Interview with Hiring Manager
Virtual Mock Discovery Meeting
Virtual Panel Interview
Final Interview
Benefits and Compensation:
Meaningful Equity Stake
Subsidized Medical, Dental, and Vision insurance plan options
401(k)
FSA, HSA and commuter benefits
Learning stipend
Open vacation policy, including:
Guidance of 15 days PTO annually
Stepful closed the last week of December
15 work-from-anywhere days
10 public holidays observed for 2025
The target base salary range for this opportunity is $120,000 - $160,000, and is part of a competitive total rewards package including equity and benefits. Individual pay may vary from the target range and is determined by a number of factors including experience, internal pay equity and other relevant business considerations.
Stepful is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex, marital status, ancestry, disability, genetic information, veteran status, gender identity or expression, sexual orientation, pregnancy, or other applicable legally protected characteristic.
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