Agile Replatforming for Checkout Launch

Project Background

ShopWave, a mid-market ecommerce platform, is replacing its legacy checkout service with a new modular checkout stack to support faster feature delivery and reduce payment failures. You are the program manager leading execution across engineering, product, QA, and go-to-market. The team uses Agile today, but delivery has been inconsistent: sprint commitments are missed, dependencies are discovered late, and stakeholders want more predictable launch planning.

The project team includes 10 engineers, 2 QA engineers, 1 designer, 1 product manager, and you. Leadership wants the first production launch in 14 weeks because the current checkout failure rate is affecting holiday revenue forecasts. The migration matters because checkout drives 38% of company revenue and the legacy system takes 3 weeks to release even small changes.

Key Stakeholders

The VP of Product wants visible customer-facing improvements by the end of the quarter. The Engineering Director wants the team to maintain sustainable Agile practices and avoid cutting core reliability work. Sales is pushing for a promotional launch date tied to a major merchant conference. Customer Support wants better internal tooling before rollout because they handle payment issue escalations.

Constraints

• Timeline: 14 weeks to launch an MVP
• Budget: $180,000 remaining for vendor support, testing tools, and contractor QA
• Team capacity: 14 core team members; no additional full-time headcount
• Dependency: payment gateway certification requires 3 weeks and can only begin after end-to-end test readiness
• Scope: MVP must support card payments, promo codes, and order confirmation emails

Complications

1. Two senior backend engineers are each allocated 25% to production support on the legacy checkout.
2. Marketing has already announced a conference demo in Week 10, four weeks before the target launch.
3. A critical fraud rules API owned by another team has no committed delivery date.

Your Task

1. Create an Agile execution plan for the 14-week delivery, including sprint structure and milestones.
2. Explain how you would manage scope trade-offs while protecting the MVP launch date.
3. Define stakeholder communication and decision-making cadences.
4. Identify the top delivery risks and mitigation plans.
5. Specify launch readiness criteria, rollback planning, and post-launch success metrics.