Senior Account Executive, Healthcare

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. We were named the #1 EdTech company in the U.S. by TIME for 2025.

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:
As a Senior Account Executive, you'll own and strategically navigate the full sales cycle for high-value, complex deals—from sophisticated prospecting and executive-level engagement through negotiation and close. You'll not only contribute directly to revenue targets but also play a critical role in shaping our go-to-market strategy, refining sales processes, and mentoring emerging talent within the team. This is an opportunity to make a substantial impact in a fast-paced, mission-driven startup at the forefront of healthcare workforce transformation.

What you'll do:

• Lead and strategically manage the full sales cycle for enterprise-level healthcare providers and systems, consistently exceeding aggressive revenue targets.

• Develop and execute a comprehensive strategic account plan to penetrate target organizations, identify key decision-makers (VP- and C-level executives in HR, Talent Acquisition, Operations, and Nursing Leadership), and uncover their most pressing workforce challenges.

• Cultivate a robust, self-generated sales pipeline through expert outbound prospecting, strategic networking, and highly effective inbound lead conversion.

• Drive deeply consultative conversations with senior leadership, diagnosing complex workforce and capacity challenges and crafting bespoke Stepful solutions that deliver significant ROI and long-term value.

• Architect and present tailored proposals, sophisticated business cases, and compelling presentations that resonate at an executive level and guide prospects through intricate buying processes.

• Forge strong, collaborative relationships cross-functionally with Customer Success, Program Operations, Solutions Architects, and RevOps to ensure seamless client onboarding, successful program implementation, and sustained customer advocacy.

• Act as a market expert, representing Stepful at industry conferences, high-level onsite meetings, and strategic events to deepen engagement, gather market intelligence, and expand our footprint.

• Contribute to the evolution of Stepful's sales strategy and processes, sharing best practices, identifying areas for improvement, and potentially mentoring junior Account Executives.

What you'll bring:

• 10+ years of progressive sales experience, with a proven track record of consistently exceeding large quotas ($1M+ ARR focus) in healthcare, education, or workforce development.

• Extensive experience closing complex, multi-stakeholder deals ($250K–$1M+) with VP- and C-level executives in enterprise healthcare systems or hospitals.

• Deep familiarity with the provider-side healthcare industry, including a nuanced understanding of their talent acquisition, human resources, and operations teams' pain points and strategic objectives.

• Exceptional ability to build rapport, tell highly compelling stories, and skillfully drive urgency and decision-making within a complex sales cycle.

• A highly data-driven, strategic self-starter mindset with a relentless bias toward execution and problem-solving.

• Demonstrated ability to thrive and lead in fast-paced, ambiguous startup environments with evolving processes, taking initiative and driving clarity.

• Strong mentorship capabilities or a desire to contribute to the growth and development of a sales team.

Bonus points if:

• Have directly sold SaaS solutions into large healthcare systems or hospital networks.

• Possess a strong network within healthcare HR, Talent Acquisition, Workforce Development, and Learning & Development leadership.

• Have experience influencing product or go-to-market strategy based on customer insights.

Interview Process

1. Intro Call with Talent Team

2. Interview with Hiring Manager

3. Mock Discovery call

4. Virtual Panel Interview w/ Cross-functional Partners

5. Final Interview w/ Co-Founder

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

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.