Once you make it up the gondala to Little Hell in Aspen, you will encounter a woman in a wheelchair named The Gift, with Pizepi in the room with her. Be respectful and courteous in your conversation with The Gift, and she will let Pizepi go.
If you talk to Pizepi in the hallway after the conversation, she will say she needs time to recover and to come talk to her after everything is over. Once you've dealt with Victory Buchanan, she will be at the entrance to the ski loft on your way out and will offer to join you. Accept her offer and the achievement will pop.