Company Context

TaskFlow is a B2B workflow automation SaaS company serving 12,000 small and mid-sized businesses. The product has strong adoption among operations teams, but customer satisfaction has stalled as engineering output has increased.

Problem

Over the last two quarters, TaskFlow shipped 18 roadmap items, yet NPS stayed flat at 24 and support tickets about "basic usability issues" rose 22%. In customer interviews, users say the product is powerful but frustrating: setup is confusing, error messages are vague, and common workflows require too many steps. Engineering leaders believe they are moving quickly, but PM leadership suspects the team does not deeply understand customer pain points and is optimizing for feature delivery over user outcomes.

You are the product manager for TaskFlow's core workflow builder. Your VP asks you to create a repeatable approach to ensure the engineering team understands real customer pain points and uses that understanding in day-to-day product decisions.

Deliverables

1. Define how you would diagnose whether engineering truly understands customer pain points today.
2. Propose a system, rituals, and artifacts that connect engineers directly to customer insight.
3. Explain how you would prioritize which pain points the team should focus on first.
4. Define how you would measure whether this approach is improving product decisions and customer outcomes.
5. Identify key trade-offs and risks in exposing engineers more directly to customer feedback.

Constraints

• You have one design lead, eight engineers, and one user researcher shared across three product squads.
• The team must continue delivering committed roadmap work for the next quarter; you cannot pause feature development.
• Customer-facing teams already complain about too many ad hoc requests for interviews.
• Any new process should be lightweight enough to sustain beyond one quarter.