So far, one must re-authenticate every time its browser or PC is restarted, for security. The result is not a fancy User Experience.
I guess many users have a "trusted" PCs or laptops for a day-to-day work. Many online services offer to skip authentication (or make less frequent) if on a trusted client. Trust is an opt-in choice, possibly gained by IT permission or using more secure authentication methods, like 2-factor. Authentication remains required on a one-time client, for example when login from someone else's laptop.
AFAIK, Google Suite does this.
Thank you for sharing this feedback. Given that Aha! is used to store both strategic and tactical product information, we have implemented security best practices to ensure your data is always protected. So whenever a browser is completely closed or a computer is restarted, we require reauthentication. You can read more about our security practices here. At this time, we are unlikely to change this behavior.