Enterprise Account Executive (Healthcare OR Retail)
Flip•New York, NY
•$125,000 - $200,000•Hybrid
About The Position
Flip is seeking a driven Enterprise Account Executive to join their AI rocketship. This role is crucial for expanding Flip's go-to-market strategy, targeting either the Retail (eCommerce & Consumer Brands) or Healthcare (Urgent Cares & Healthcare Providers) sectors. The ideal candidate is a "mercenary of CX" who thrives in a fast-paced startup environment and is passionate about driving net-new revenue and dismantling outdated systems with AI-powered solutions. This position reports directly to the Chief Customer Officer.
Requirements
- Experience in startup tech sales (B2B SaaS, AI/ML, cloud, etc.) preferred
- Proven success in enterprise, multi-threaded sales cycles (ideally $500K+ ACV)
- A natural-born closer who destroys quota
- Sells solutions, not features
- Deeply understands stakeholder pain and uses it to build trust fast
- Thrives in chaos, moves fast, and outworks the market
Responsibilities
- Drive net-new revenue across MM and Enterprise accounts ($50K–$250K+ deals and beyond)
- Build trust with senior stakeholders and earn the right to own mission-critical customer interactions
- Partner closely with Product, Engineering, and Customer Success to shape the platform through real customer insight
- Move fast, challenge legacy processes, and help build a world-class GTM engine
- Target elite retail and ecommerce brands, protecting and enhancing brand voice and customer experience at scale
- Navigate organizations where CX is deeply tied to revenue, loyalty, and conversion
- Build relationships with CX, Digital, and Ecommerce leaders in the retail sector
- Position Flip as a competitive advantage in a crowded, high-expectation market
- Target leading healthcare systems and provider groups
- Replace legacy communication systems with AI-driven patient engagement
- Navigate complex buying groups with compliance, IT, and clinical stakeholders in the healthcare sector
- Build trust in HIPAA-compliant, mission-critical workflows
- Position Flip as infrastructure for modern patient communication
Benefits
- Comprehensive healthcare
- Unlimited vacation
- Mandatory half week off for everyone over July 4th
- Full week off at the end of the year
- Bonus and/or commission
- Equity, in accordance with company policy, and subject to board approval
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What This Job Offers
Job Type
Full-time
Career Level
Senior
Education Level
No Education Listed
