Project Context

HubSpot's internal revenue systems team is replacing a legacy CRM workflow used by 180 sales reps with a new lead-routing and account assignment process before the start of Q4. You are the program manager leading a 9-person cross-functional team: 4 engineers, 1 data analyst, 1 designer, 1 QA lead, 1 sales operations manager, and 1 product manager. The project is urgent because the current workflow causes duplicate account ownership and delayed lead follow-up, costing an estimated $420K per quarter.

One senior engineer, who owns the legacy routing service, is technically strong but difficult to work with. He frequently dismisses planning meetings, challenges scope decisions in front of stakeholders, and refuses to document dependencies unless asked repeatedly. His work is critical because 60% of the migration depends on his service knowledge.

Key Stakeholders

The VP of Sales wants the new workflow live by September 25 to support Q4 pipeline generation. The Engineering Manager wants to avoid burnout and does not want the difficult engineer overloaded. The Head of Sales Operations wants zero disruption to lead assignment during the cutover. Finance supports the project only if it stays within the approved budget.

Constraints

• Deadline: 10 weeks, with launch required by September 25
• Budget: $95,000 remaining for contractor QA, training, and change management
• Team capacity: No additional full-time headcount approved
• Dependency: Legacy routing documentation is incomplete; only one engineer fully understands fallback logic
• Cutover limit: Maximum 2 hours of lead-routing downtime

Complications

1. The difficult engineer has already said the deadline is unrealistic and is pushing for a 4-week delay.
2. Sales leadership has promised regional managers there will be no changes to territory rules, but the current design requires 3 rule changes to reduce duplicates.
3. QA found that 8% of test leads are being assigned to the wrong owner in staging.

Deliverables

1. Create a 10-week execution plan with milestones, owners, and dependency management.
2. Explain how you would work with the difficult engineer while keeping the project on track.
3. Recommend trade-offs on scope, timeline, or rollout approach.
4. Define launch readiness criteria, rollback conditions, and post-launch monitoring.
5. Identify the top risks and mitigation actions you would communicate to stakeholders.