This document proposes a new platform called NightCap that matches junior illustrators with clients like art directors. It notes the challenges junior illustrators face in getting work through current methods like Instagram which only yield a 5% response rate. NightCap would allow illustrators and clients to create profiles, be matched based on project needs and location, and message each other directly to schedule interviews. Statistics are provided on the number of junior illustrators and art directors in the US to estimate the potential market size of such a platform. Different interface styles are suggested and user testing is proposed to ensure the needs of art directors are met.