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Head of Customer Success



Customer Service, Sales & Business Development
Kansas City, KS, USA
Posted on Friday, June 7, 2024

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.

Your Mission:

As the Head of Success, you’ll be responsible for building and managing a Customer Success team that proactively drives a world class customer experience. Customer Success is the face of Sailes and is tasked with ensuring customer satisfaction, retention, and expansion. You will play a critical role in shaping our customer experience strategy as well as the evolution and growth of our customers.

  • Customer Experience Expert: Understands the full lifecycle of the customer experience and can identify when executed poorly or at a high level. Can deliver sound tactics to prevent churn and deliver exceptional experiences across entire customer base.
  • Skilled Communicator: Exceptional communication skills, both written and verbal. Ability to communicate directly and with empathy to customer, especially through listening and subsequent action.
  • Logical & Analytic: You hate misleading statements, sloppy thinking, circular reasoning, logical fallacies, and other abominations. Able to structure and process qualitative or quantitative data and draw insightful conclusions from it. Exhibits a probing mind and achieves penetrating insights.
  • Team Builder: Source, select, and sell great people to join our company team. Once on board, coach the team in their current roles to improve performance, and prepare them for future roles.
  • Organization & Planning: Scopes, plans, organizes, schedules, and budgets in an efficient, productive manner. Focuses on key priorities.
  • Commitment to Deep Research: Understands that the source of our high-quality content comes from the sheer amount of research we are willing to do.
  • High Standards: Expect personal and team performance to be nothing short of their best
  • Attention to Detail: Does not let important details slip through the cracks or derail a project
  • Honest/Integrity: Does not cut corners ethically. Earn trust and maintains confidences. Does what is right, not just what is politically expedient. Speaks plainly and truthfully.
  • Self Aware: When you don’t know something, you’re very good at learning it, even from primary resources. When you lack an understanding, you don’t delude yourself into thinking you are an expert.
  • Retention Expert: Has previous experience driving positive retention through proven strategies and tactics


  • 5+ years of experience leading customer-facing organizations
  • Ability to manage influence through persuasion, negotiation, and consensus building.
  • Ideally combined background of post-sale and sales experience
  • Strong empathy for customers AND passion for revenue and growth
  • Deep understanding of value drivers in recurring revenue business models
  • Demonstrated desire for continuous learning and improvement.
  • Enthusiastic and creative leader with the ability to inspire others
  • Excellent communication and presentation skills
  • Previous success in a fast-paced, startup environment preferred.
  • “Change the future” work ethic
  • Desire to develop, plan, and implement new processes and strategies to continually improve the customer experience.
  • Good listener and great question-asker with a knack for translating customer feedback into actionable items for our customers and the Product team.