CSM Team Lead

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, execution quality, strong account ownership, and scalable processes are critical to retention and expansion.

This role is remote and requires full English fluency while supporting U.S. customers on Eastern Standard Time.

Role Overview

Whippy is seeking a Customer Success Manager Lead to oversee and elevate our Customer Success Managers responsible for ongoing account ownership.

You will manage CSMs who own complex, long-term customer relationships. Your focus is ensuring consistent execution, strong judgment, early risk identification, and scalable solutioning across accounts. You will also act as an escalation point when needed.

This role requires strong people management, process ownership, and enough technical fluency to coach CSMs on how to customize Whippy for customer operations without creating fragile or unscalable solutions.

⚡ What You’ll Do

• Lead Customer Success Managers

  • Manage and develop Customer Success Managers responsible for ongoing customer relationships.

  • Set expectations for account ownership, cadence, documentation, and follow-through.

  • Review account plans, notes, and activity to ensure consistent execution.

• Coach on Account Strategy and Judgment

  • Coach CSMs on identifying churn risk, expansion signals, and misaligned requests.

  • Help CSMs improve how they push back, frame tradeoffs, and guide customers.

  • Review calls and provide direct feedback on execution quality and decision-making.

• Own Process Quality for Customer Success

  • Ensure success plans, check-in cadences, and documentation are created and maintained.

  • Identify where processes are breaking and fix them.

  • Balance structure with flexibility as customer complexity grows.

• Act as Escalation and Support on Key Accounts

  • Join customer calls when needed for escalations, renewals, or strategic reviews.

  • Support complex solutioning conversations without owning day-to-day execution.

  • Ensure escalations are resolved with long-term outcomes in mind.

• Support Technical Solutioning Standards

  • Ensure CSMs are designing scalable workflows and AI agent configurations.

  • Evaluate whether solutions will hold up at scale or create long-term issues.

  • Know when to involve engineering versus adjusting process or configuration.

🎯 What We’re Looking For

• Experience managing or mentoring Customer Success Managers.

• Strong ownership mindset around process, quality, and outcomes.

• Comfort giving direct feedback and holding teams accountable.

• Experience overseeing complex or long-term customer relationships.

• Technical fluency with SaaS platforms, workflows, automations, or integrations.

• Ability to evaluate solutions without deep engineering expertise.

• Excellent English communication with U.S. customers.

• Bias toward proactive execution and long-term retention.

🙌 What We Offer

• Competitive compensation with performance-based leveling

• Clear ownership over Customer Success execution and team quality

• Direct collaboration with founders and senior leadership

• A fast-growing AI company with real customer complexity

• The opportunity to reduce founder involvement in day-to-day accounts