Renewal and Expansion Specialist (LATAM, Remote)
About 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. We are at $6M ARR, bootstrapped, and scaling fast.
Read this before applying.
This is NOT a billing admin role. It is NOT a renewals processing role. It is NOT a call center role. This is a commercial specialist seat that owns every dollars-and-contracts conversation across our existing customer base. You will be on live Zoom calls with customers discussing pricing, overages, upgrades, and contract terms daily. If you cannot do proration math live on a call while holding a conversation, this role is not for you.
About This Role
At Whippy, our Customer Success Managers are technical operators. They configure AI agents, build workflows, and drive adoption. They do not run commercial conversations. That is your job.
You own the full commercial surface area on our existing customer base. Renewals, upgrades, downgrades, expansions, proration math, contract creation, Stripe billing issues, and MSA paperwork. You take the call when a CSM flags an account for a commercial conversation. You plant seeds for cross-sell during renewal calls and hand warm opportunities to the sales team. You are not hunting new logos and you are not processing paperwork after someone else closes. You are the person on the call, doing the math, proposing the structure, and getting it signed.
This role requires commercial instinct, contract literacy, composure under pressure, and the ability to reason through numbers in real time. Candidates who panic when a customer is frustrated, who cannot do contract math live, or whose default is to escalate will not succeed here.
What You Will Do
Run commercial calls with existing customers including renewals, upgrades, downgrades, expansions, and billing conversations
Do contract math live on customer calls including proration, package comparisons, overage analysis, and credit reconciliation
Draft and send contracts for existing customers including amendments, renewals, and supersession agreements with prorated credits
Own Stripe-related billing issues for existing accounts including invoice disputes, subscription changes, refunds, and payment method updates
Partner with CSMs on account health signals and take the call when they flag an account for a commercial conversation
Plant seeds for cross-sell and new products during renewal calls and hand qualified opportunities to the sales team
Maintain accurate records of contract terms, renewal dates, and commercial commitments across the customer base
What We Are Looking For
Real direct customer-facing commercial experience, you have negotiated renewals, upgrades, or contract terms with customers personally, not just processed paperwork after someone else closed
Ability to do proration and package comparison math live on a call without freezing or going silent
Composure under pressure, customers on these calls are often frustrated and you must absorb that, stay calm, propose something fair, and close the conversation cleanly
Contract and billing fluency, you have drafted or amended real contracts and understand proration, credits, term resets, and supersession
Experience with Stripe or a similar billing platform
Strong written English, every commercial call ends in a follow-up email that summarizes terms and sends the contract
Ambition to grow into a broader commercial or revenue operations role over time
Not a Fit
If you have only worked in billing operations, accounts receivable, or scripted support without direct customer-facing commercial conversations, do not apply. If your most recent role was at a BPO or call center, do not apply. If you are a hunter looking to close new logos, this is not that role.
Location
Open to candidates anywhere in Latin America. Candidates based in Buenos Aires, Argentina are strongly preferred as we have a WeWork office in Vicente Lopez. EST hours required. Full English fluency required.
Compensation
Competitive compensation based on experience, including monthly performance bonuses tied to net revenue retention and expansion, WeWork membership, and more.