Hi Ben,
You can't modify the sidebar in Cockpit to add Success Plans, it only includes List, Reports and Playbooks. However, you can do two other things to bring visibility to Success Plans.
1) Users can create a custom Cockpit View which only includes Success Plans Objective CTAs and Group that View by Customer. This will give them a succinct View of the Objectives for each customer. Let me know if you want to go this route, and I will email you concise directions you can send to them - it's very easy. Here is the link to the article on creating Customer Cockpit Views:
https://support.gainsight.com/Product_Documentation/CTAS_Tasks_and_Playbooks/User_Guides/04_Create_C...
2) You can move Success Plans up toward the top of the Customer360. I would suggest placing it right under the Cockpit section in the C360, so users can easily choose to view/work on Success Plan Objectives or other CTAs in the Cockpit. To reorder the C360 sections, go to Administration, then C360 Layouts. From there you can choose the sections you want in the C360 Layout (you can create different ones for different groups!) and drag and drop them to be in the order you like. Here's a link on how to create and modify C360 Layouts:
https://support.gainsight.com/Product_Documentation/Customers_and_Relationships/Admin_Configuration/...
Tracy