Account Executive (Healthcare OR Retail)

Flip; New York (NY); On-site; USD 70,000 - 100,000; Full time

Benefits offered by this job

Comprehensive healthcare

Unlimited vacation

Mandatory time off in July and December

Job summary

Flip is hiring an Account Executive to lead a go-to-market expansion in the Retail and Healthcare sectors. This role demands driving net-new revenue and building critical customer relationships while ensuring service excellence.

The ideal candidate excels in startup leadership and has a track record of exceeding sales goals, particularly in tech-focused environments. The position offers a salary range of $70,000 – $100,000 along with eligibility for bonus and equity.

Qualifications

• Preferably experienced in startup tech sales with proven success in complex, multi-threaded sales cycles.
• Natural-born closer; able to exceed sales quotas.
• Product-oriented with a deep understanding of stakeholder pain points.

Responsibilities

• Drive new revenue across major and enterprise accounts.
• Build trust with senior stakeholders to manage customer interactions.
• Collaborate with cross-functional teams to shape the platform using real customer insights.

Skills

B2B SaaS sales experience

AI/ML knowledge

Strong closing skills

Customer relationship management

Job description

Title

Account Executive (Healthcare OR Retail)

Reporting to

Chief Customer Officer

Location

Marina del Rey, CA OR Brooklyn, NY (Onsite Monday - Friday)

Who Is Flip?

Flip delivers Voice AI solutions that answer customer calls for eCommerce brands and healthcare providers, handling millions of conversations monthly.

The Tech Behind the Revolution

Our platform embeds into a company’s tech stack to personalize interactions and resolve issues in seconds.

• Retail: we power high‑volume, brand‑sensitive customer interactions, protecting voice, driving conversions, and elevating CX at scale.
• Healthcare: we deliver HIPAA‑compliant, clinically reliable AI that manages patient communication, scheduling, and inquiries with precision and empathy.

The Role: Join the AI Rocketship

Reporting directly to the Chief Customer Officer, you will lead a GTM expansion that dismantles outdated systems across the Retail or Healthcare sectors, driving high‑velocity AI transformation.

Core Responsibilities

• Drive net‑new revenue across MM and Enterprise accounts ($50K–$250K+ deals and beyond)
• Build trust with senior stakeholders and earn ownership of 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

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 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 (Urgent Care & 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

Who You Are

• A Natural‑Born Closer: you don’t hit quota—you destroy it
• Product Obsessed: you sell solutions, 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 complex, multi‑threaded sales cycles (ideally $500K+ ACV)

More About Us

• We’re international: United States, United Kingdom, and Canada
• We’ve raised $30M+ to date, including a recent $20M Series A
• We offer 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
• In‑office 5 days per week across NYC, LA, and UK offices

Compensation

Salary range: $70,000 USD – $100,000 USD. Role is eligible for bonus, commission, and equity per company policy and board approval.

Equal Employment Opportunity

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.