Didn’t find a solution to this known problem - but will really love to find one! 

great question! this certainly is a challenge when leveraging role hierarchy because under the role hierarchy structure, opportunities are assigned to a specific user. sounds like you’ve explored the capabilities of territory hierarchy, which would naturally support your ask since opportunities are assigned to a territory instead of a user. however, transitioning from role to territory hierarchy shouldn’t be taken lightly.

an option we’ve had some customers in the same situation explore is creating a custom user reference field and stamping that with the manager at close. this method is more beneficial than rolling up historicals on the sales rep because typically the first line manager is more stable in terms of movement than reps. 

from there you’d create a new mode within Clari Studio’s Field Config with the owner field being the custom user reference field and subsequently leverage this new mode across Clari to view historicals. something to keep in mind is you wouldn’t be rolling up on sales reps anymore but given your issue is the result of sales reps transitioning this should alleviate the issue as long as first line managers aren’t transitioning nearly as often.