Automated Tax Calculations in Bulk

Hi everyone,

We have a requirement where US sales tax needs to be calculated in bulk over Opportunities and Billings that are auto generated in a yearly cycle on subscription renewal.

Given that there are thousands of records that are automatically generated and sent we can't have someone press the 'calculate tax' button on each record individually.

We're having trouble getting clear answers on how to achieve this with either the native solution or with Avalara.  Has anyone else met this requirement?

Ideally we would trigger the tax calculation using a trigger or automation once the records are created.