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 and experienced Enterprise Account Executive to join our Sales team. You’ll be responsible for generating new business by building meaningful relationships with healthcare organizations, identifying their workforce needs, and positioning Stepful as a strategic solution.
You’ll own the full sales cycle—from prospecting through close—and play a key role in expanding Stepful’s footprint across the healthcare ecosystem.
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
Interview with cross-functional Leader
Virtual Panel Interview + Presentation
Final Interview
Benefits and Compensation:
Meaningful Equity Stake
Subsidized Medical, Dental, and Vision insurance plan options
401(k)
FSA, HSA and commuter benefits
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.
What We Do
Stepful unlocks the full potential of the global workforce, improving access to quality healthcare for everyone, everywhere.
Our platform is designed for working adults, particularly from historically underserved communities, providing virtual instructor-led courses that include live, cohort-based learning sessions and one-on-one coaching for those looking for entry-level positions in hospitals and healthcare settings.
Stepful graduates, primarily from underrepresented communities, go on to work at leading healthcare institutions such as CVS, Walgreens & NY Presbyterian Hospital. Stepful is backed by Y Combinator, Reach Capital and AlleyCorp and recently closed a round led by Oak HC/FT.
Why Work With Us
At Stepful, we’re on a mission to transform lives. We’ve grown to 20K+ students in just a few years, helping people launch healthcare careers they never thought possible. We use cutting-edge AI to scale human connection—and we don’t wait for opportunity. We create it, together.
Gallery
Stepful Offices
Hybrid Workspace
Employees engage in a combination of remote and on-site work.
At Stepful, we balance flexibility with in person connection. We're hybrid in-office Tues-Thurs to collaborate, with 15 work from anywhere days annually, a week off between Christmas & New Year’s, and open vacation—because rest fuels impact.
