I'd set it up like this:
BA => (rqTimeoutMsg) => GDA => TM (waits) => BA => (confirmation) => TM => GDA
BA = your business actor
GDA = a guaranteed delivery actor (Akka.Persistence)
TM = timeoutManager
BA sends a 'timeout' request to the 'GDA' which forwards it to the Timeout manager. It waits until time X (using Scheduler, I'd suggest) then sends the 'timeout' to BA, which should confirm it back to TM or directly to GDA.
The GDA and TM together form a persistent TimeoutManager, so they could/should be wrapped together in one Actor, which is the one the BA talks to (requestTimeout, and upon receiving 'timeout', confirmReceptionOfTimeout).
Question however: how do you plan to make sure the BA is there after a (crash+)restart?