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Enterprise Account Executive



Sales & Business Development
New York, NY, USA
Posted on Saturday, March 30, 2024

Stop searching and start Saileing → Sailes is sales, with AI

Sailes envisions a world where technology creates the space for us all to be more human. Our mission is to help every sales team unlock potential and act on possibilities.

Today, we elevate the world’s leading sales executives with Sailebots that eliminate manual prospecting tasks in favor of high-value, high-return sales activities.

For the Fortune 500 and beyond, our unique Sailebots automate the entire prospecting lifecycle. This Digital Labor™ process helps companies triple their pipeline at a 5X cost reduction from manual prospecting. Join us to be a part of the exciting world of AI-driven sales solutions.

Role Description

As an Enterprise Account Executive at Sailes, you will play a pivotal role in managing full-life cycle sales strategies to acquire new accounts (500 employees and up) while maintaining customer relationships within the first year. Your primary responsibility is to lead the entire sales process, from researching and prospecting to advising, negotiating contracts, and closing deals.

Performance Requirements

  • Alongside your very own Sailebot, you will consistently practice your inherent prospecting abilities via the channels of your choice
  • Conduct discovery calls to uncover and address business challenges that Sailes can solve
  • Demonstrate how Sailes provides tailored solutions to meet prospect's key outcomes
  • Collaborate effectively with cross-departmental teams and Dir of Sales on emerging vertices and strategies
  • Negotiate contracts ranging from five to mid-six figure annual contracts
  • Exceed quarterly revenue targets, building consistent down-stream pipeline
  • Understand prospect’s needs to develop accurate scoping and success criteria for successful implementation
  • Own customer expansions within the first 12 months, providing an exceptional account management experience to customers, including account performance reviews
  • Consistently demonstrate a willingness to learn more and sell innovative solutions that are being created today


  • Minimum of two years of sales lifecycle management experience, preferably in a SaaS environment
  • Ability to manage and navigate complex sales cycles averaging 3-9 months with contract values starting at 5 figures upwards
  • Proven experience in selling disruptive, complex solutions into medium to large organizations
  • A thought leader in sales technologies and GTM processes
  • Strong written and spoken communication and the ability to communicate abstract value into tangible results
  • Ability to build and cultivate strong, trusting relationships and partnerships
  • Strong pipeline management and negotiation skills


  • Unlimited, commission-driven compensation with base salary, accelerators, and zero earnings cap