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Director of Customer Success

WhippyRemote - Worldwide
Remote Full-time

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Experience Level

Mid to Senior

Qualifications

Candidates should possess a strong technical background with hands-on experience in engineering roles such as Solutions Engineer, Deployment Engineer, or Technical Implementation Consultant before transitioning into customer success. Experience leading teams in a technical environment is essential.

About the job

About Whippy

Whippy builds AI-powered communication tools for major staffing and workforce companies across the United States. Our platform connects voice, SMS, chat, and automation to help businesses run more efficiently. We are bootstrapped, growing quickly, and have reached $6M in annual recurring revenue. Our post-sales team is essential for customer retention and expansion, making this leadership hire a key priority.

Important Application Requirement

This role requires a strong engineering or technical implementation background. Candidates must have hands-on experience as a Solutions Engineer, Deployment Engineer, Technical Implementation Consultant, or a similar technical role before moving into customer success leadership. We cannot consider applicants with only customer success or account management backgrounds. The Director will oversee Deployment Engineers who write production code, so technical credibility and the ability to engage with CTOs is required.

Role Overview

This is a player-coach position. The Director of Customer Success manages Whippy's most important enterprise accounts directly and leads a team of Customer Success Managers and Deployment Engineers based in LATAM. The role involves setting standards, building playbooks, and ensuring technical conversations are accurate and productive. When customer issues arise, this leader is the primary escalation point.

This is a rare chance to shape the customer success function at a fast-growing, founder-led AI company. There is a clear path to advance to Head of Customer Success and eventually VP as Whippy continues to scale.

Key Responsibilities

  • Own a portfolio of Whippy's most critical enterprise accounts
  • Lead and mentor Customer Success Managers and Deployment Engineers across LATAM
  • Build customer success playbooks, onboarding frameworks, health scoring metrics, and team standards from scratch
  • Act as the escalation point for complex and high-stakes customer situations
  • Conduct Quarterly Business Reviews, account assessments, and executive-level meetings with enterprise clients
  • Work directly with the CEO and CTO to monitor team performance, customer satisfaction, and influence product direction
  • Support hiring and onboarding as the team grows
  • Serve as a bridge between US-based customers and the LATAM execution team

Location

This is a remote role open to candidates worldwide.

About Whippy

Whippy is at the forefront of AI communication solutions, assisting major staffing and workforce companies in the U. S. to replace outdated manual processes with innovative AI technologies. Our commitment to customer satisfaction and operational excellence drives our rapid growth, and we are proud to be a bootstrapped company with ambitious goals.

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