+1000 from my end. The moment you end up helping bigger Sales teams, this becomes a pain, and you have to build intricate workflows to cater for all the needs.
If it helps, I've set this up by creating a territory list for each reps territory, using custom properties to indicate the territory element I need. Then I use a workflow to automatically assign new contacts and companies to the right rep based on the territory information. All of our forms request the mandatory information to make this work as well (geography, industry zones, etc.). It would be great if HS came up with a native process for this, but there are definitely ways to make this work right now.
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