Common early stage trap: always chasing The Biggest Deal Yet. "We closed a $20k deal, $40k is next!" "$40k closed, $60k is next!" "$60k closed, $90k is next!" Most companies hit a ceiling and struggle to break through instead of focusing on medium-sized deals that close easily.
The best gut heuristic I've heard for this is: If you close a deal for $(x), and want to move up market to n(x), close n contracts at $(x) before moving up. Repeat until time to close hits some threshold
