Launch ChatGPT Insights Pilot

Project Background

OpenAI wants to launch a new ChatGPT Insights pilot for enterprise customers: a lightweight analytics surface that summarizes workspace usage, common prompt themes, and admin-level adoption trends. The feature is intended to support renewals for Q4 enterprise contracts, so leadership wants an initial pilot live in 10 weeks.

You are the program owner coordinating a 12-person cross-functional team across product, engineering, data science, design, legal, and GTM. The project is high-visibility because Sales has already identified 8 design-partner customers who want access this quarter, while Legal is still reviewing what usage data can be surfaced safely.

Key Stakeholders

The Head of Enterprise wants a pilot in market quickly to support renewals. Legal and Privacy want conservative data exposure rules and may delay launch if controls are unclear. Engineering wants to avoid building custom reporting pipelines that will create long-term maintenance burden. Sales wants the broadest possible feature set for the 8 design partners, even if that increases scope.

Constraints

Timeline: 10 weeks to pilot launch
Budget: $180,000 for vendor support, analytics tooling, and user research
Team: 12 people; no additional headcount approved
Dependency 1: Privacy review must be completed by end of Week 4
Dependency 2: Admin event logging quality is currently only 92% complete, but launch requires at least 98% coverage for pilot metrics
Dependency 3: Design partner onboarding materials must be ready 2 weeks before launch

Complications

In Week 2, Sales asks to add team-level benchmarking between customer workspaces, which Legal flags as higher risk.
In Week 5, the data engineering lead reports that event logging remediation will take 2 extra weeks unless scope is reduced.
One of the 8 design partners expects access by Week 8 due to a renewal deadline.

Your Task

Build a 10-week execution plan with milestones, owners, and dependency management.
Recommend how you would handle the added benchmarking request and the Week 8 customer pressure.
Define launch scope for an MVP versus deferred items.
Identify the top risks, mitigations, and rollback criteria.
Specify success metrics for the pilot's first 30 days.

Project Background

Key Stakeholders

Constraints

Timeline: 10 weeks to pilot launch

Budget: $180,000 for vendor support, analytics tooling, and user research

Team: 12 people; no additional headcount approved

Dependency 1: Privacy review must be completed by end of Week 4

Dependency 2: Admin event logging quality is currently only 92% complete, but launch requires at least 98% coverage for pilot metrics

Dependency 3: Design partner onboarding materials must be ready 2 weeks before launch

Complications

In Week 2, Sales asks to add team-level benchmarking between customer workspaces, which Legal flags as higher risk.

In Week 5, the data engineering lead reports that event logging remediation will take 2 extra weeks unless scope is reduced.

One of the 8 design partners expects access by Week 8 due to a renewal deadline.

Your Task

Build a 10-week execution plan with milestones, owners, and dependency management.

Recommend how you would handle the added benchmarking request and the Week 8 customer pressure.

Define launch scope for an MVP versus deferred items.

Identify the top risks, mitigations, and rollback criteria.

Specify success metrics for the pilot's first 30 days.

Problem

Project Background

Key Stakeholders

Constraints

Complications

Your Task

Launch ChatGPT Insights Pilot

Problem

Project Background

Key Stakeholders

Constraints

Complications

Your Task