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Rippling's Escalation Team Traces Root Causes

by Matt McGinnis on December 28, 2025

Situation

  • Rippling, a rapidly growing business software platform valued at over $16 billion with 5,000+ employees, needed a systematic approach to handle customer-reported issues
  • The company was experiencing the typical challenges of scaling quickly while maintaining product quality
  • Traditional support approaches were resolving surface-level problems but not addressing deeper systemic issues
  • Matt McGinnis, as CPO (formerly COO), recognized that simply fixing individual bugs wasn't enough to maintain product excellence at scale

Actions

Created a Dedicated Escalations Team

  • Formed a specialized team specifically focused on handling escalated customer issues
  • Selected team members who were "particularly skilled at pistol whipping other people in the company to get to real root causes"
  • Positioned the team to have authority to drive cross-functional investigations

Implemented a Multi-Level Root Cause Analysis Process

  • Rejected superficial fixes that merely addressed symptoms ("we fixed the data error and shut the ticket down")
  • Required tracing issues through multiple layers: from customer-facing problems to underlying software issues
  • Mandated identifying the "system that created the software that created the data error"
  • Ensured complete resolution by addressing all levels of the problem chain

Established an Escalation-Friendly Culture

  • McGinnis personally championed the value of escalations, calling them "a gift"
  • Encouraged customers (including founders of companies they'd invested in) to escalate issues directly
  • Maintained a personal queue of reported issues to take directly to product teams
  • Created public feedback channels where executives openly discussed product issues

Results

  • Created a system that not only fixed individual issues but improved the underlying processes
  • Established a mechanism to "iterate on the processes so that the system that builds the system can get better"
  • Developed institutional knowledge about failure patterns that could be addressed systematically
  • Maintained product quality while scaling rapidly in a complex business software environment
  • Contributed to Rippling's ability to expand beyond its initial HR/payroll focus into a comprehensive business platform

Key Lessons

  • Treat escalations as gifts: "There's no greater gift to me as a product executive than receiving an escalation from a customer."
  • Pursue true root causes: Don't stop at fixing the immediate issue; trace problems back to their systemic origins.
  • Create specialized expertise: Some people excel specifically at driving deep problem-solving across organizational boundaries.
  • Solve at multiple levels: Address both the immediate customer issue and the underlying systems that created it.
  • Make escalation frictionless: When leaders treat feedback as valuable rather than burdensome, they receive more actionable intelligence.
  • Use public channels: Sharing issues openly creates learning opportunities for the entire organization.
  • Maintain a personal connection: Even as CPO, McGinnis maintained a personal queue of customer issues to ensure executive visibility.