Strategy question
Imagine your top 5 enterprise prospects each require a different long-tail connector to buy, while current customers are pushing for richer integrations with systems like Slack, Jira, and Salesforce. How would you collect and weight customer signals, segment the opportunity, and turn that into a 12-month connectors roadmap that leadership, engineering, and go-to-market teams will support?
- Glean
- Strategy
- Hard
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What this question tests
Tests turning conflicting connector signals, from top prospects and existing customers, into a defensible 12-month roadmap that leadership, engineering, and go-to-market can commit to.
How to approach it
- Collect signal systematically: revenue tied to each top-5 prospect's required long-tail connector, and ticket or request volume from existing customers for Slack, Jira, and Salesforce depth.
- Segment the opportunity into two tracks: deal-driven connectors, narrow but high revenue certainty if closed, and platform-driven connectors, broader reach across the existing base.
- Weight platform-driven connectors, Slack, Jira, Salesforce, higher for sustained roadmap investment, since they compound value across current and future customers, not just one deal.
- Weight deal-driven long-tail connectors case by case, only committing engineering time when the deal size and probability of closing justify the dedicated build.
- Build the 12-month roadmap in two parallel tracks with clear checkpoints, quarterly reviews of deal-driven builds against actual deal progress, and phased delivery of the platform connectors.
- Present the roadmap to leadership with the weighting logic explicit, so future one-off prospect requests get evaluated against the same framework instead of relitigating priorities.
What a strong answer includes
- Splits the roadmap into two explicit tracks, deal-driven and platform-driven, rather than one flat prioritized list.
- Weights platform connectors like Slack, Jira, and Salesforce higher by default, since they serve the existing base and future prospects alike.
- Builds a checkpoint into deal-driven connector commitments, tied to actual deal progress, avoiding sunk investment if a deal stalls.
- Presents a reusable weighting framework to leadership, so future prospect requests don't require re-litigating the whole roadmap.
Common mistakes
- Committing full engineering time to a prospect's requested connector before the deal has meaningfully progressed.
- Treating all customer requests as equally strategic without separating one-off from broadly reusable connectors.
- Building a roadmap with no checkpoints, so a stalled deal wastes months of dedicated engineering work.
Likely follow-up questions
- How would you handle it if a top prospect's deal collapses mid-build?
- What would move a request from platform-driven to a fast-tracked exception?
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Learn the skill behind it
Chapters of the AI PM course that teach what this question tests.
- Chapter 4: Discovery and strategy for AI products
- Chapter 9: Prove it paid off: outcomes, economics, and pricing
- Chapter 14: Get the job: the AI PM interview loop