Enterprise Account Executive (Healthcare OR Retail)

Flip•Los Angeles, CA

5h•$70,000 - $100,000•Onsite

About The Position

Flip is seeking "mercenaries of CX" to join their AI rocketship as Account Executives, specializing in either the Healthcare or Retail sectors. This role reports directly to the Chief Customer Officer and is crucial for leading Go-To-Market expansion to dismantle outdated systems. The ideal candidate will thrive in a high-velocity AI transformation environment and contribute to building a world-class Go-To-Market engine. The company emphasizes a strong team culture, hard work, and innovation, with offices in NYC, LA, and the UK. Flip's AI technology integrates directly into a company's tech stack to personalize interactions and resolve complex issues, offering advanced solutions for both retail customer engagement and HIPAA-compliant healthcare communication.

Requirements

Experience in startup tech sales (B2B SaaS, AI/ML, cloud, etc.) preferred
Proven success in complex, multi-threaded sales cycles (ideally $500K+ ACV)
You sell solutions, retail or provider wins, not features
You deeply understand stakeholder pain and use it to build trust fast
You thrive in chaos, move fast, and outwork the market
Operate with uncompromising integrity

Nice To Haves

You don’t hit quota—you destroy it
You are a natural-born closer

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 (Retail focus)
Protect and enhance brand voice and customer experience at scale (Retail focus)
Navigate orgs where CX is deeply tied to revenue, loyalty, and conversion (Retail focus)
Build relationships with CX, Digital, and Ecommerce leaders (Retail focus)
Position Flip as a competitive advantage in a crowded, high-expectation market (Retail focus)
Target leading healthcare systems and provider groups (Healthcare focus)
Replace legacy communication systems with AI-driven patient engagement (Healthcare focus)
Navigate complex buying groups with compliance, IT, and clinical stakeholders (Healthcare focus)
Build trust in HIPAA-compliant, mission-critical workflows (Healthcare focus)
Position Flip as infrastructure—not a tool—for modern patient communication (Healthcare focus)