Enterprise Healthcare Sales Executive

Stepful • New York, NY

3d • $120,000 - $160,000

About The Position

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.

Requirements

• 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

Nice To Haves

• You've sold directly to healthcare systems or hospitals
• You have experience selling into healthcare-focused HR and talent acquisition teams

Responsibilities

• 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

Benefits

• 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.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed
• Number of Employees: 11-50 employees