Project Context

You are the program manager for ShopFlow, a B2B e-commerce and logistics platform that powers order capture, inventory allocation, and fulfillment for mid-to-large retailers. One of your largest customers, NorthPeak Outfitters (≈$1.2B annual revenue, 380 stores in the US/Canada, ~22M monthly web sessions), is running on ShopFlow’s legacy Order Management System (OMS v1). OMS v1 is stable but increasingly expensive to maintain and lacks modern capabilities NorthPeak needs: split-ship optimization, real-time inventory promises, and better fraud hooks.

ShopFlow has built OMS v2, which improves allocation accuracy (expected +1.5–2.0% reduction in cancellations), supports same-day fulfillment routing, and reduces operational toil via automated exception handling. Internally, leadership wants NorthPeak migrated before the holiday peak because OMS v1 has a known scaling risk under high promotion traffic. However, NorthPeak’s Store Operations leadership is openly resistant: they’ve trained 2,400 associates on the current workflows, fear disruption, and believe “the old system works.”

You have 10 weeks to execute a migration plan that includes change management, training, and a safe launch. There is a hard change freeze starting Week 9 (peak-season readiness) during which NorthPeak will not accept any production changes that could affect store fulfillment.

Stakeholder Landscape

NorthPeak stakeholders are not aligned:

• VP Store Operations (NorthPeak): Strongly resistant to change. Measured on store productivity and fulfillment SLA. Believes new workflows will slow associates and increase mis-picks.
• Director of E-commerce (NorthPeak): Wants OMS v2 for better delivery promises and fewer cancellations; pushing for aggressive rollout.
• NorthPeak IT Applications Manager: Concerned about integration risk with their ERP and WMS; wants extensive testing and clear rollback.
• ShopFlow Sales Director: Has renewal negotiations in 4 months; wants a “success story” and is worried resistance will jeopardize the relationship.
• ShopFlow Engineering Manager (OMS v2): Has a roadmap commitment to two other customers and can only allocate limited engineering time for bespoke migration support.

Constraints

Deliverables (What you must produce)

1. A stakeholder and change-management plan specifically addressing Store Ops resistance (messaging, incentives, training approach, and decision forums).
2. A week-by-week execution plan (10 weeks) including milestones, dependencies, and a go/no-go framework before the freeze.
3. A launch strategy (e.g., pilot stores, phased rollout, parallel run, feature flags) and a rollback plan that NorthPeak IT will sign off.
4. A trade-off proposal: what you would cut, defer, or simplify to hit the deadline without compromising safety (be explicit about scope).
5. Success criteria and monitoring for the first 30 days post-migration (operational and business metrics).

Complications

1. Union training rules: Store associates can only be trained in 2-hour blocks, and training must be scheduled 2 weeks in advance. Store Ops refuses “extra” training time during peak staffing constraints.
2. Integration instability: In early testing, OMS v2 occasionally produces a different allocation decision than OMS v1 for ~0.8% of orders due to new optimization logic. E-commerce loves it; Store Ops calls it “unpredictable.”
3. Resource squeeze: Two of the six ShopFlow engineers are on an on-call rotation for another customer’s Black Friday readiness and can’t commit to nights/weekends.

Your interviewer will evaluate how you drive alignment, handle a resistant client stakeholder, make credible trade-offs, and execute a safe launch under a hard freeze date.