I booked flights using Chase UR points I earned on my Chase Sapphire Reserve via the Chase UR Travel Portal
We are supposed to leave next Tuesday but just heard that my grandfather passed away this morning. Will the Sapphire Reserve trip cancellation insurance cover this? It's not clear to me as I paid entirely using points and nothing was charged to my card for the airfare
Have been on hold with them for 15+ mins now
Yes. They'll either pay you the $ value of the ticket, or $0.01 per UR point.
Also note that many airlines allow for refunds even on non-refundable tickets in the case of a death of a close family member. Read the Contract of Carriage for the airline you bought the ticket from to see, or try googling.
Make sure you cancel your itinerary before departure time, if you want to think about going the airline refund route. They can probably reinstate your ticket for a death in the family but it's additional hassle.