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.