Enterprise Healthcare Sales Executive

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.