restart a program based on repeated errors in it's log file

Hi :)

how would one approach to automatically restart a windows software on a pulseway managed windows client on repeated error messages that it writes to a log file in it's directory?

What I'd like to achieve is for example

for: C:\examplesoftware\program.exe
that writes a log C:\examplesoftware\log.txt
on the e.g. 3rd appearance of e.g. "Session Timeout to server"
exit C:\examplesoftware\program.exe
wait e.g. 30 seconds
run C:\examplesoftware\program.exe again
and continue monitoring C:\examplesoftware\log.txt

Would this be possible? I didn't find a windows based software that could do this so my hope would be that maybe pulseway can :)
Thanks in advance for any helpful suggestions