About Whippy

Whippy is leading the way in AI-powered business communication, helping companies replace manual workflows with intelligent AI agents across voice, chat, and messaging. We work closely with enterprise staffing and workforce organizations, embedding AI agents and automation directly into their ATS and CRM systems.

As Whippy adoption grows, the quality of onboarding, workflow design, and long-term account ownership directly impacts retention and expansion. We are building a Customer Success function that is structured, scalable, and independent from founder oversight.

This role is remote and must overlap with U.S. Eastern Time while supporting U.S.-based customers.

Role Overview

Whippy is hiring a Head of Customer Success to own Net Revenue Retention, customer architecture, and Customer Success team performance.

You will lead and elevate our CSM team while designing the systems, standards, and guardrails that ensure scalable solutioning across accounts.

You will design the operating system for Customer Success at Whippy and reduce founder involvement in day-to-day account execution.

You will operate as a player-coach, personally owning a small portfolio of strategic accounts while building a high-performance team around you.

Core Responsibilities

Own Net Revenue Retention

You will own retention performance across the customer base.
You will implement structured health scoring, renewal forecasting, and risk identification systems.
You will build frameworks that surface expansion signals early and reduce churn before it materializes.
You will define what “healthy account ownership” looks like across the team.

Architect Customer Success Systems

You will design and standardize onboarding frameworks and implementation workflows.
You will define solutioning guardrails to ensure AI agent configurations and automations are scalable and not fragile.
You will codify best practices for embedding Whippy into ATS and CRM environments.
You will ensure implementation quality holds up at scale across enterprise staffing customers.
You will identify where processes are breaking and redesign them.

Lead and Elevate the CSM Team

You will manage and develop Customer Success Managers responsible for ongoing customer relationships.
You will set clear standards for account ownership, documentation quality, follow-through, and judgment.
You will review calls and provide direct feedback on execution quality and pushback discipline.
You will coach CSMs to balance flexibility with architectural integrity.
You will hold the team accountable to retention and expansion outcomes.

Strategic Account Ownership

You will personally own a small portfolio of high-impact, complex accounts.
These accounts will typically represent our largest customers or those requiring architectural judgment and executive alignment.
You will protect long-term solution design, guide renewal strategy, and ensure scalable implementation standards.
You will not operate as a high-volume CSM. Your ownership will focus on strategic revenue protection and architectural integrity.

Own Escalation Structure

You will serve as the senior escalation point when architectural judgment or executive presence is required.
You will resolve escalations with structural fixes rather than short-term patches.
You will define when issues require engineering involvement versus process adjustment.

Cross Functional Alignment

You will partner closely with Product and Engineering to surface patterns across customers.
You will translate customer complexity into structured feedback that informs product decisions.
You will ensure Customer Success and Product remain tightly aligned as complexity grows.

Reduce Founder Dependency

You will build a Customer Success organization that operates independently from founder oversight.
You will create systems that allow leadership to focus on product and growth rather than daily account decisions.
Success in this role means the founders are no longer required in routine customer escalations.

What We’re Looking For

Experience building or scaling Customer Success at a high-growth B2B SaaS company.
Direct ownership of retention, churn reduction, or expansion metrics.
Experience managing and elevating Customer Success Managers.
Strong systems thinking and comfort designing onboarding frameworks and workflow standards.
Experience working with integrations, APIs, automations, or complex SaaS implementations.
Ability to evaluate solution architecture without being an engineer.
Comfort giving direct feedback and holding teams accountable.
Executive presence with U.S.-based enterprise customers.
Bias toward structured execution, scalable systems, and long-term retention.

Nice to Have

Experience working with staffing, workforce, or ATS platforms.

Experience building Customer Success operations from early stage to scale.

Background in Technical Account Management, Solutions Architecture, or Customer Success Operations.

What Success Looks Like in the First 6 Months

A clearly defined onboarding and implementation framework adopted across all accounts.
Standardized documentation and escalation processes.
A measurable improvement in churn visibility and renewal forecasting.
Reduced founder involvement in day-to-day account decisions.
Stronger pushback discipline and solution consistency across the CSM team.

Compensation

Compensation will reflect senior-level ownership of Net Revenue Retention and Customer Success performance. Base salary and variable structure will align with responsibility for retention outcomes and team performance.

Whippy

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Head of Customer Success