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Job description
Head of Enterprise Sales – Healthcare RCM
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Location : Remote – United States
Compensation : $165K–$195K base | $330K–$390K OTE + equit
About the Company
TwentyAI has partnered with a fast-growing, venture-backed healthcare technology company transforming revenue cycle management through AI-driven automation. Its platform helps healthcare providers automate RCM workflows, accelerate cash flow, reduce administrative burden, and modernize the patient financial experience.
The company is hiring a Head of Enterprise Sales to lead and strengthen its enterprise revenue organization during its next stage of growth
The Opportunity
This is a hands-on leadership role managing experienced Enterprise Account Executives selling complex, six- and seven-figure solutions to healthcare organizations.
The ideal candidate brings direct healthcare RCM sales experience, a proven record of closing enterprise deals, and experience managing and developing sellers. This person will remain actively involved in strategic opportunities—joining customer calls, shaping deal strategy, coaching discovery, and helping move complex deals through close.
This is not a passive forecasting role. The company needs a leader who can improve sales execution while driving predictable revenue performance.
What You’ll Be Doing
Lead, coach, and develop a team of Enterprise and Strategic Account Executives.
Drive revenue across complex, six- and seven-figure healthcare RCM opportunities.
Improve discovery, workflow diagnosis, executive engagement, and value articulation.
Coach sellers on multi-threading, business-case development, competitive positioning, and closing strategy.
Establish disciplined pipeline reviews, deal strategy, forecasting, and performance management.
Strengthen outbound accountability, pipeline coverage, and opportunity creation.
Partner with Sales Development, Marketing, Partnerships, and leadership to improve pipeline and win rates.
Use conversion data to identify performance gaps and guide coaching.
What We’re Looking
For7+ years of B2B SaaS sales experience, including significant enterprise selling exposure.
Direct experience selling RCM technology or services to healthcare providers.
A track record of personally closing complex, six- and seven-figure enterprise deals.
Experience managing and coaching Enterprise Account Executives.
Strong knowledge of healthcare revenue cycle workflows, buyers, and financial outcomes.
Ability to engage senior leaders across revenue cycle, finance, operations, and technology.
Experience with methodologies such as MEDDPICC, Challenger, or GAP Selling.
Consistent success against revenue and pipeline-generation targets.
A data-driven, hands-on leadership style suited to a fast-moving startup.
Preferred Experience
Experience selling AI, automation, or workflow technology within healthcare.
Leadership experience at an early-stage or high-growth SaaS company. xhqgsiq
Experience building or improving an enterprise sales operating cadence.
Worksite address
united, PA, 15689, US
Who can apply
Review the original listing for work authorization, qualifications and employer requirements.