Autopilot Relationship Prioritization & Proactive Insights (Top 100 Contacts)

Details:

For users with large networks (e.g., 3,000+ contacts), the biggest challenge is prioritization, not data entry or chat-based querying. Users can realistically maintain meaningful relationships with only a subset (e.g., ~100 contacts), but Dex does not currently help surface who those people should be or how to deepen those relationships over time.

Request to evolve Dex from a reactive tool into a proactive relationship engine that works on the user’s behalf.

Key ideas:

Automatically identify a user’s most important contacts based on signals like interaction frequency, recency, notes, meetings, messages, and relationship history

Continuously re-rank and adapt this list as relationships change

Proactively surface insights such as:

“These 5 important people are overdue for a check-in”

“Someone in your top contacts is in town”

“You’ve been interacting less with this previously important relationship”

Reduce reliance on chatbot prompts — insights should appear automatically, not require daily manual queries

Improve UI to surface these priorities clearly, since the current interface becomes a bottleneck at scale