Head of Customer Success

Head of Customer Success

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. Our post-sales team is the reason customers stay and grow and this hire is the most important one we are making right now.

Read this before applying.

This role requires an engineering or technical implementation background. MUST have previously worked as a Solutions Engineer, Deployment Engineer, Technical Implementation Consultant, or in a similar hands-on technical role before moving into customer success leadership. Pure CS or account management profiles will not be considered regardless of seniority. You will be managing Deployment Engineers who write production code. You must be technically credible enough to evaluate their work and hold your own on a call with a CTO.

About This Role

This is a player-coach role. You will personally own Whippy's most strategically important customer accounts while building and leading a mixed team of CSMs and Deployment Engineers across LATAM. You are the person we call when something goes wrong with a customer. You are the person who builds the playbooks, sets the standard, and makes sure Jack is not the only technical person on every call.

This is a ground-floor leadership opportunity at a bootstrapped AI company growing fast with no VC overhead. The person who executes well in this role grows into Head of CS and eventually VP as we scale.

What You Will Do

• 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

What We Are Looking For

• Engineering or technical implementation background, this is required not preferred. Previous role as a Solutions Engineer, Deployment Engineer, Implementation Consultant, or similar before moving into CS leadership

• Direct management experience, you have hired, coached, given feedback, and handled underperformance

• Hands-on understanding of APIs, webhooks, and integrations from real experience, not just conceptual awareness

• Proven ownership of complex enterprise customer relationships end to end

• Builder mentality, you have created playbooks, frameworks, and processes from a blank page not just followed them

• Strong English communication, written and spoken, for daily enterprise Zoom calls and direct CEO reporting

Location

Open globally. LATAM candidates based in Buenos Aires or Mexico City are strongly preferred. US-based candidates will be considered for the right profile. EST or CST hours required. Full English fluency required.

Compensation

Competitive compensation based on experience, including performance bonus, equity, WeWork membership, and more.