twentyAI · 1 week ago
Enterprise Account Executive - TWE43773
TwentyAI has partnered with a rapidly scaling healthcare technology organization that’s reinventing how providers manage patient billing, financial engagement, and revenue operations. They are seeking a seasoned Enterprise Account Executive who thrives in full-cycle selling and can win complex, six-figure deals with major healthcare providers.
Responsibilities
Run the full sales motion: prospecting, discovery, demos, negotiation, and closing
Build and manage a targeted territory using multi-channel outbound strategies
Sell directly to senior operational and financial leaders within health systems and large medical groups
Deliver highly tailored demos that solve real financial and workflow challenges
Partner closely with sales leadership to sharpen ICP, messaging, and GTM strategy
Use tools like Salesforce, LinkedIn Sales Navigator, Gong, and AI platforms to accelerate deals
Bring field insights back to the product and GTM teams
Consistently exceed quota and pipeline creation goals
Qualification
Required
4+ years of closing experience in SaaS (healthtech, fintech, or startup background is ideal)
A true hunter — you know how to build pipeline from scratch and run sophisticated outbound motions
Strong discovery and storytelling abilities; comfortable selling to VP and C-suite stakeholders
Experience with multi-threaded, mid-market/enterprise deals
Highly adaptable, curious, and energized by fast-moving environments
Must be based in the SF Bay Area and willing to be in-office three days a week
Benefits
Unlimited PTO
Fully-paid medical, dental, and vision for you + dependents
401(k) w/ company match
Student loan assistance