At first, you need to find out, why the Pulseway service fails to start when you reboot your system. Please look into the Windows event log -> Application to find out what is the error? If the error is, that service failed to start in 30 seconds, then at first try to set the service startup as Automatic (delayed start), but if that doesn't help, then you can try to increase the startup timeout by running built-in script 'Increase Windows Service Timeout at Startup' (If required, then you can adjust the timeout interval. In this script, it is set to 60000ms [60 seconds]. Our customers get the best results if they set the timeout to 90000ms [90 seconds], but you will need to test it).
Also please check other windows event log logs, whether there are no other event entries related to the Pulseway service at the startup.
In order to edit this script you will need to open the Pulseway WebApp -> Automation -> Built-in, then copy the script 'Increase Windows Service Timeout at Startup' and edit it.
In order to run this script you will need to go to the Systems tab -> Systems -> select the required system -> Scripts -> Built-in -> select the script 'Increase Windows Service Timeout at Startup' and run it.