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.
Responsibilities
- 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.
Requirements
- 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.
Nice to 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.
