Work happens across Slack, Notion, Linear, GitHub, meetings, and the desktop. The problem is not a lack of tools. It is the context lost between them.

In this episode, Nik Singh sits down with Parris Khachi to explore Highlight's approach to proactive workplace AI. Parris explains why the next AI interface may not be a chat box and how Highlight uses screen, meeting, and integration context to make assistance more proactive.

The conversation also covers privacy and user control, individual versus team context, model economics, product-led adoption, competition with incumbents, and why teams should automate coordination without outsourcing judgment.

Highlight AI: https://highlightai.com/
Parris Khachi: https://www.linkedin.com/in/parris-k-7928b011/
Terminal Value: https://www.youtube.com/@Terminal-Value-Podcast

Chapters
00:00 Cold open
00:56 Introduction
01:31 Where context gets lost across work tools
05:03 Highlight's mission and the coordination tax
06:04 The AI intern that follows the work
13:01 Screen context, privacy, and user control
18:18 Choosing models across capability, speed, and cost
21:43 Ideal users, deployment, and adoption
27:28 How AI could change team structure
29:32 Competition and the interface after chat
33:51 Highlight's long-term vision
36:10 Closing takeaways

Disclaimer: For information and education only; not investment advice or a recommendation to buy or sell securities. Views are the speakers' own.