CEO OS

Gokul Rajaram — AI and Deal Velocity

Source: @gokulr on X


Two Complications for AI-First Product Sales

1. AI Committees

Many enterprises are drafting AI policies right now. Deals go into AI committee reviews, causing delays. Sometimes the deal changes the policy, which further lengthens the timeline.

2. Category Creation / Land and Expand

Many AI products — even when significantly valuable — are not an established need yet. They're creating a new category.

  • Deals start smaller. The motion is land and expand.
  • A deal that would eventually be $150K will start as a $30K land in 3 months, then take another 3-9 months to expand to $150K.

Advice

Be patient. Deals taking longer than ideal is normal and natural due to AI reviews and category creation. Don't slavishly apply a framework — use first principles thinking.

Connected (1)

Private. Behind Cloudflare Access. © Karthik Kamalakannan.