About the job
About Whippy
Whippy builds AI-powered communication tools for some of the largest staffing and workforce companies in the U. S. Our platform helps these organizations automate voice, SMS, chat, and other workflows, replacing manual processes with intelligent agents. With $6M in annual recurring revenue, Whippy is a bootstrapped company growing quickly.
Important Note Before Applying
This is not a billing administrator, call center, or paperwork processing role. The Commercial Renewal and Expansion Specialist manages all commercial conversations with established customers. Expect to join daily live Zoom calls to discuss pricing, overages, upgrades, and contract terms. Comfort with proration math during these discussions is essential. Candidates looking for a purely administrative or behind-the-scenes position will not find this role a fit.
Role Overview
The Commercial Renewal and Expansion Specialist leads commercial conversations with Whippy’s current customers. This includes handling renewals, upgrades, downgrades, expansions, proration math, contract creation, Stripe billing issues, and MSA paperwork. When a Customer Success Manager identifies an account needing a commercial discussion, this specialist steps in. The role also involves surfacing cross-sell opportunities during renewal talks and providing warm leads to the sales team. This is not a new business development or post-sale paperwork job. The specialist runs the call, handles calculations in real time, proposes contract structures, and secures signatures.
Success requires strong commercial judgment, a solid grasp of contracts, calm under pressure, and the ability to work through numbers on the spot. Those who struggle with frustrated customers, contract math during calls, or tend to escalate rather than resolve issues will find this role challenging.
Key Responsibilities
- Lead commercial calls with existing customers, covering renewals, upgrades, downgrades, expansions, and billing topics.
- Work through contract math live on customer calls: proration, package comparisons, overage calculations, and credit reconciliations.
- Prepare and send contracts for current customers, including amendments, renewals, and supersession agreements with prorated credits.
- Resolve Stripe billing issues for existing customers.
Location
This is a remote position open to candidates based in Latin America.

