Head of Customer Success

About the Company

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.

Responsibilities

• 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

Requirements

• Engineering or technical implementation background (Solutions Engineer, Deployment Engineer, or Implementation Consultant)
• Direct management experience including hiring, coaching, and performance management
• Hands-on understanding of APIs, webhooks, and integrations
• Proven ownership of complex enterprise customer relationships
• Builder mentality with experience creating processes from scratch
• Strong English communication skills for enterprise calls and executive reporting
• Ability to work EST or CST hours

Benefits

• Competitive compensation based on experience
• Performance bonus
• Equity
• WeWork membership