TITLE: Enterprise Account Executive (Healthcare OR Retail)

REPORTING TO: Vice President of Sales

Who Is Flip?

Ever call your favorite eCommerce brand or healthcare provider, and have a crazy good Voice AI 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 roller coaster, and have a great Flippin 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 Reporting directly to our Chief Customer Officer, you’ll help lead a GTM expansion designed to dismantle outdated systems across the Retail or Healthcare business sectors.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

What makes Retail unique: Speed, volume, and brand sensitivity. You’re selling into environments where every interaction impacts revenue and perception instantly.

• Healthcare (Urgent Cares & Healthcare Providers):
• 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

What makes Healthcare unique: Trust, compliance, and precision. You’re selling into environments where every interaction impacts patients and operational integrity.

Who You Are: You’re not just an AE—you’re a force of nature.

• A Natural-Born Closer: You don’t hit quota—you destroy it
• 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)

More About Us

• We're international, spanning the US, UK, and Canada
• We’ve raised +$30M to date including our recent $20M Series A - backed by Ridge, Next Coast, ScOp, Bullpen Capital, Data Point and Forum Ventures, as well as founders & executives from Amazon Alexa, Ada, Attentive, and Simon Data
• Comprehensive healthcare and unlimited vacation, including a mandatory half week for everyone over July 4, and a full week off at the end of the year