Whippy

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.

• Personally own a portfolio of Whippy's most strategically important enterprise accounts • Manage and develop a team of CSMs and Deployment Engineers across LATAM • Build CS playbooks, onboarding frameworks, health scoring, and team standards from scratch • Act as the escalation point for complex and high-stakes customer situations • Run QBRs, account reviews, and executive-level conversations with enterprise customers • Partner directly with the CEO and CTO on team performance, customer health, and product direction • Support hiring and onboarding as the team scales • Be the bridge between our US customer base and our LATAM execution team

• Own a portfolio of assigned customer accounts end to end • Run daily Zoom calls including onboarding, training, troubleshooting, and check-ins • Help customers configure and use the Whippy platform correctly • Troubleshoot issues and coordinate with the Deployment Engineer when needed • Guide customers on best practices, AI agent setup, campaign logic, and workflow design • Proactively monitor customer usage and reach out before customers tell you something is wrong • Identify expansion opportunities and surface them to the team

• Own and enforce structured onboarding, documentation quality, meeting discipline, and success planning standards across all accounts. • Review calls, provide feedback, and hold CSMs accountable to preparation, follow through, and architectural integrity. • Personally manage a small portfolio of high impact accounts, ensuring strong retention, clear success metrics, and expansion awareness. • Create visibility into onboarding timelines, account health, risk signals, and expansion opportunities. • Partner with Product and Engineering to surface patterns and ensure scalable, durable solution design.