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Whippy
Whippy
11 – 50 Employees
RecruitmentSaaS
Whippy is a SaaS company building an omnichannel AI communications platform for businesses. Its cloud-based tools combine SMS, voice and VoIP, chatbots, campaigns, workflow automations, and integrations to help teams manage recruiting, sales, customer support, and reception workflows. Whippy’s AI assistants support candidate outreach, lead qualification, and customer conversations across languages and communication channels, including around-the-clock interactions.
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Head of Operations - Remote United States

Lead billing, contracts, recruiting, compliance, and operational systems at Whippy, an AI communications platform. Build the operations team and processes needed to support scale.

USUnited StatesRemoteFull-timeLeadEnglish RequiredOperations
ERP

Description

  • Lead revenue operations across billing, collections, payments, quote-to-cash, sales operations, commissions, deal desk support, HubSpot administration, and account changes.
  • Manage contracts with company templates, including order forms, MSAs, NDAs, and partner agreements.
  • Oversee vendors and SaaS tools, covering renewals, usage audits, seat counts, and spending.
  • Administer partner revenue sharing, payments, records, pipeline management, and co-marketing logistics.
  • Run recruiting operations for open positions through the process up to final interviews.
  • Manage sourcing, outreach, scheduling, the Ashby pipeline, offers, Deel, onboarding, offboarding, PTO, expenses, and review cycles.
  • Hire and manage an Operations Associate.
  • Create documented processes that junior employees can execute independently.
  • Own enterprise security and data review materials while advancing SOC 2 readiness.
  • Manage access controls, security during offboarding, and tools that reduce financial or data leakage risk.
  • Advance the company’s operating cadence, partner strategy and enablement, pricing and deal modeling, and industry expansion research.
  • Reconcile systems, resolve overdue invoices, and shift operational ownership from the CEO.

Requirements

  • Experience establishing an operations function from the ground up.
  • Practical experience with billing, collections, contracts, and business systems.
  • Experience managing people and creating processes that others can run independently.
  • Experience handling important matters involving partners, vendors, and customers.
  • Willingness to remain hands-on during the first six months.
  • Highly organized, with clear written communication and the confidence to be direct with a founder.
  • Fluent written and spoken English.
  • Ability to work US Eastern hours.
  • Experience working at a SaaS company.
  • Staffing or HR technology experience is helpful but not required.
  • The application requests experience personally administering tools such as Stripe, HubSpot, Salesforce, an ERP, PandaDoc or DocuSign, Deel, or an ATS.

Benefits

  • Join a bootstrapped, profitable company.
  • Work remotely.
  • Build and lead the operations function.
  • Take on a broadening scope in a high-growth environment.
  • Gain exposure to operating cadence, partner strategy, pricing, deal modeling, and industry expansion research.
  • Choose a flexible location across Latin America or the United States.
  • Access a WeWork office in Buenos Aires.

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