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About This Role:

  • Own the full commercial surface area on our existing customer base.
  • Plant seeds for cross-sell during renewal calls and hand warm opportunities to the sales team.
  • Be the person on the call, doing the math, proposing the structure, and getting it signed.

What You Will Do:

  • Run commercial calls with existing customers; draft contracts; own Stripe-related billing issues.
  • Partner with CSMs on account health signals; plant seeds for cross-sell; maintain records of contract terms.

What We Are Looking For:

  • Real direct customer-facing commercial experience and contract/billing fluency.
  • Ability to do proration and package comparison math live on a call, with composure under pressure.
  • Strong written English and ambition to grow into a broader commercial or revenue operations role.

Whippy

Whippy is a fast-growing AI communication platform helping some of the largest staffing and workforce companies in the United States replace manual workflows with intelligent AI agents across voice, SMS, chat, and automation. The company is at $6M ARR, bootstrapped, and scaling fast; they value people with commercial instinct and contract literacy.

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