Value Proposition & Positioning~20 min
Positioning: Pick the Fight You Can Win
You built a lightweight project tracker for two-person design studios. Demos go great — until the prospect says: "So it's like Jira?"
You say "sort of, but simpler," and watch the deal die. Against Jira you have fewer features, fewer integrations, and no enterprise security page. Against Jira, you lose every time.
Here's the twist: half your paying customers weren't using Jira before you. They were using a shared Google Doc and vibes.
What actually killed the demo?