Hi Luke,
I would prioritize the "quick wins" first. Relatively quick to deploy, and has a high impact. Some criteria I look at is if it is high volume, repetitive, frequent, and impacts several users. You also have to build in some X-Factor where the team that screams the loudest or has the most pain gets a slight edge in priority.
I've also seen some companies implement a Winshuttle steering committee. They get an Executive sponsor and nominate some key users. Then, they participate in a monthly meeting to discuss all things Winshuttle and review the priority list together.
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Yoon Chung | SE
Winshuttle North America
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