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