Maintaining Context in Long-Running GPT-4o API Conversations for Executive Desktop Application?

Hello OpenAI Community,

We’re developing a desktop application targeting C-suite executives that uses the GPT-4o API for ongoing contextual assistance. Our application needs to maintain conversation context across multiple sessions while being mindful of token usage and response quality.

Specifically, we need advice on:

  1. What’s the optimal approach for managing conversation history with GPT-4o when executives may have intermittent conversations spanning days or weeks?
  2. Are there recommended token management strategies to balance context retention with cost efficiency? (Currently considering window-based truncation and summary techniques)
  3. What’s the best way to handle topic transitions within the same conversation thread without losing relevant context?
  4. Has anyone implemented effective context persistence techniques that don’t rely solely on passing the full conversation history each time?
  5. Are there specific prompt engineering approaches that work well with GPT-4o to help it retrieve relevant information from earlier in the conversation?

Any insights from those who’ve built similar executive-facing tools would be much appreciated.