Senior Account Executive, Healthcare

About Stepful:

At Stepful, we’re on a mission to reimagine allied healthcare training by providing affordable, online, instructor-led and AI-enabled education to help learners - especially from underserved communities - launch high-demand healthcare careers on their own terms. In addition to our direct-to-consumer training model, Stepful partners with healthcare institutions to build talent pipelines and career pathways in an effort to mitigate the increasing allied health employee shortage. Our graduates - inclusive of Medical Assistants, Pharmacy Technicians and more - go on to work for leading institutions such as CVS, NY-Presbyterian and Walgreens.

Stepful is backed by Y Combinator, Reach Capital and AlleyCorp, and we recently closed a $31.5M Series B round led by Oak HC/FT. Additionally, TIME named Stepful the #1 EdTech company in the U.S. for 2025.

Stepful unlocks the full potential of the global workforce, improving access to quality healthcare for everyone, everywhere.

Our values:

At Stepful, we attribute much of our success to the high caliber of our team. To that end, we seek to onboard mission-driven individuals who thrive in a fast-paced environment, don’t shy away from ambiguity and demonstrate our four company 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.

About the Role
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.

You're a Great Fit If You Have

• 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 You

• 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

Stepful is an equal opportunity employer. We welcome applicants from all backgrounds and are committed to creating an inclusive workplace.

At Stepful, we're an equal opportunity employer and value diversity at our company. We do not discriminate based on race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.