Management chain human task approval doesn't work

Content

My use case: 

Everyone in my organization has a manager, and every management chain ends with our CEO / President (one person/role).  I want to build an approval, using one human task (can have multiple stages), that starts with the manager of the creator and goes all the way up to the CEO (but excludes the CEO), and instead ends with our Senior Vice President of Human Resources (a role we have).

So let's say we have the following management chain

Chris - Customer Service Rep

Jen - Customer Service Manager

Scott - Director of Customer Service

Tim - COO