Project Context
Rippling is launching automated payroll tax filing for Canada to expand its payroll product beyond the US. The project has been running for 10 weeks with a 20-person cross-functional team, but an executive review shows the launch is now 5 weeks behind against a fixed regulatory deadline tied to the start of the new tax quarter. If the team misses the date, Rippling will lose an estimated $1.8M in near-term ARR and delay signed customer commitments.
Key Stakeholders
The GM of Payroll wants the full feature set launched on the original date because Sales has already committed to 25 mid-market customers. The Head of Compliance will not approve launch without province-level filing accuracy and audit logs. The Engineering Manager is concerned that two senior engineers are split across this project and a production reliability initiative, while Customer Success wants enough lead time for training and migration support.
Constraints
- Deadline: 8 weeks remaining until quarter start; no extension possible
- Budget: $220,000 remaining; no new full-time headcount approved
- Team: 12 engineers, 2 designers, 2 QA, 2 compliance specialists, 1 PM, 1 data analyst
- Dependencies: external tax filing vendor certification, legal sign-off, customer migration tooling
- Current status: 37% of planned scope complete; integration testing has not started
Complications
- The external filing vendor changed its API spec 3 weeks ago, creating rework for the tax calculation service.
- Three large enterprise customers are requesting custom reporting that was not in the original MVP.
- Defect rates in the last two sprints are 40% above forecast, and QA says requirements are still changing.
Your Task
- Identify how you would determine the root causes of the schedule slip within the first week.
- Build a recovery plan that gets the project back on track or proposes a credible phased launch.
- Recommend scope trade-offs and explain how you would align stakeholders with competing priorities.
- Define the milestones, owners, and decision points for the remaining 8 weeks.
- Describe the key risks, mitigations, and launch-readiness criteria you would use.
