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Enterprise Account Executive

New York

LOCATION: New York, New York (Onsite M-F)

Who The Flip Is Flip?

Flip is leading the next wave of innovation in customer support—AI-powered call automation. While it’s clear that automating support calls is inevitable and imminent, current market adoption remains under 1%. Flip is ahead of the curve, emerging as the category leader across eCommerce/Retail, Healthcare and Transportation.

Flip integrates with a client's tech stack to personalize every call and resolve issues quickly, creating a seamless, branded experience that enhances customer satisfaction and loyalty.Flip continuously evolves through millions of real customer conversations, delivering human-level understanding and handling with exceptional precision.

We are in-office, with spaces in NYC, LA, and the UK. If you enjoy being an owner-operator, solving and/or reverse hacking hurdles and hold a high level of integrity for product quality and service then this is the place for you. 

#FlippinLegend

What You Will Do

We’re looking for a high-performing Enterprise Account Executive to drive significant revenue growth within our established Retail & Consumer vertical. This is a critical, high-impact role responsible for converting existing pipeline opportunities and building net-new enterprise relationships from the ground up. You’ll act as a key driver of business development—owning the full sales cycle for complex, high-value deals and shaping how major retail and consumer brands adopt our SaaS solutions.

As a true sales hunter, you’ll bring exceptional prospecting skills, strategic deal management, and the ability to navigate enterprise sales cycles with multiple stakeholders. This role is suited for someone who thrives on building and closing, and who is energized by the opportunity to grow our enterprise footprint while helping define what success looks like in this vertical.

Key Responsibilities 

  • Identify, prospect, and close new enterprise-level B2B sales opportunities in the retail and consumer goods sectors.
  • Lead end-to-end sales cycles from discovery and solutioning to proposal, negotiation, and close.
  • Navigate complex buying groups, often involving multiple stakeholders (Marketing, Ops, Tech, CX, C-Suite).
  • Partner with Engineering, Product, and Customer Success teams to tailor offerings and ensure successful hand-offs.
  • Represent the company at key industry events, helping build our brand within target segments.
  • Own the entire sales cycle—from outbound and qualification to demo, proposal, and close—with minimal support.

Critical Success Factors 

To drive high-impact outcomes in a fast-moving, high-opportunity vertical, the Enterprise Account Executive will be expected to demonstrate agility, ownership, and consistent performance from the start. Y1 success in this role is defined by:

  • Successfully convert 40–50% of qualified opportunities in the pipeline within the first 6 months.
  • Source and progress 10–20 new high-value enterprise opportunities Y1.
  • Maintain flawless CRM hygiene, logging all activities and stage movements in real time.
  • Deliver 95%+ forecast accuracy on deals in commit and best-case categories.
  • Consistently update pipeline with clear next steps, decision criteria, and stakeholder mapping.
  • Serve as a trusted advisor in the retail/consumer space, bringing deep understanding of customer pain points.
  • Share feedback with Product and Marketing to shape positioning, messaging, and roadmap priorities.
  • Represent the company at key industry events, helping build our brand within target segments.

Experience and Professional Qualifications

  • 5–8+ years of SaaS sales experience, with a strong track record of success in enterprise-level B2B sales.
  • 2+ years of experience closing high-value deals (minimum $250K+) with large retail and/or consumer brand.
  • Demonstrated ability to own full sales cycles end-to-end, from self-prospecting to close, in a high-velocity environment.
  • Experience navigating and influencing multi-stakeholder buying groups, including VP and C-suite decision-makers with executive-level value articulation.
  • Proven success in fast-paced, high-growth, or startup SaaS environments.
  • Strong understanding of the retail/consumer ecosystem, and how technology influences CX, operations, and revenue.
  • Excellent communication, presentation, and negotiation skills.
  • Comfortable operating in a fast-paced, high-growth environment.

Bonuses

  • You understand what it looks like to work at a startup, and have an entrepreneurial drive
  • Experience working in the eCommerce/Customer Experience industry is a plus

More About Us

  • We're international, spanning the US, UK, and Canada, Australia
  • Our sales tech stack includes Hubspot, Avoma, LinkedIn, and Omni
  • We are backed by ScOp Venture Capital, Bullpen Capital, and Forum Ventures, as well as founders & executives from Amazon Alexa, Ada, Attentive, and Simon
  • 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

Our customers span the globe, and so do our offices. 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.

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