Enterprise Account Executive (Healthcare OR Retail)

New York Reporting to: Vice President of Sales Who Is Flip? Ever call your favorite eCommerce brand or healthcare provider, and have a crazy good VoiceAI answer? That’s Flip. Hundreds of brands from Under Armour and Tory Burch in retail to Experity and Fast Pace Health in healthcare trust Flip to have millions of phone calls with their customers every month. We’ve built our company on the idea that the best way to grow is to have a reference list as long as our customer list, and a constant belief that the team is the best thing we’ve built. Both are true today and increasingly so every day. Many on our team would tell you this is their favorite place they’ve ever worked, and the hardest they’ve ever worked. It’s ideal for people who want to go all‑in, do the work, ride the rollercoaster, and have a great time doing it. We’re a small and mighty team of 50 today with offices in NYC, LA, and the UK. The Tech Behind the Revolution Flip doesn’t just "answer phones." We embed directly into a company’s tech stack to personalize every interaction and resolve complex issues in seconds. In Retail , we power high-volume, brand-sensitive customer interactions—protecting voice, driving conversions, and elevating CX at scale. In Healthcare , we deliver HIPAA‑compliant, clinically reliable AI that manages patient communication, scheduling, and inquiries with precision and empathy. Our AI evolves through millions of real‑world conversations—delivering human‑level empathy, operational efficiency, and outcomes that legacy systems simply can’t match. The Role: Join the AI Rocketship We just secured our Series raise. The engines are primed. The launchpad is clear. We’re not hiring traditional "Account Executives." We’re hiring mercenaries of CX. Reporting directly to our Chief Customer Officer, you’ll help lead a GTM expansion designed to dismantle outdated systems across the Retail or Healthcare business sectors. If you want your career tied to a high‑velocity AI transformation, this is your seat. Core Responsibilities - Across the board for all our Account Executives Hunt Without Mercy : Drive net‑new revenue across MM and Enterprise accounts ($50K–$250K+ deals and beyond) Earn the Keys to the Kingdom : Build trust with senior stakeholders and earn the right to own mission‑critical customer interactions Bridge the Gap to Greatness : Partner closely with Product, Engineering, and Customer Success to shape the platform through real customer insight Burn the Playbook : Move fast, challenge legacy processes, and help build a world‑class GTM engine Vertical Focus: Where You’ll Specialize - Retail OR Healthcare Retail (Ecommerce & Consumer Brands) Target elite retail and ecommerce brands Protect and enhance brand voice and customer experience at scale Navigate orgs where CX is deeply tied to revenue, loyalty, and conversion Build relationships with CX, Digital, and Ecommerce leaders Position Flip as a competitive advantage in a crowded, high‑expectation market Healthcare 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 Build trust in HIPAA‑compliant, mission‑critical workflows Position Flip as infrastructure—not a tool—for modern patient communication Who You Are Product Obsessed : You sell solutions, retail or provider wins, not features Customer‑First : You deeply understand stakeholder pain and use it to build trust fast Startup Warrior : You thrive in chaos, move fast, and outwork the market Experience in startup tech sales (B2B SaaS, AI/ML, cloud, etc.) preferred Proven success in enterprise, multi‑threaded sales cycles (ideally $500K+ ACV) Benefits International presence spanning the US, UK, and Canada Comprehensive healthcare coverage and unlimited vacation, including a mandatory half‑week for everyone over July 4, and a full week off at the end of the year Final compensation may vary based on location, experience, and qualifications. This role is also eligible for bonus and/or commission as well as equity, in accordance with company policy, and subject to board approval. Compensation Range: $125,000 - $200,000 USD Flip is committed to providing equal employment opportunities for all employees, applicants, and covered individuals regardless of protected characteristics. We want our company to be as diverse and inclusive as our customers. #J-18808-Ljbffr Flip.to