Partonic scatterings with large momentum transfer occur before the formation of the quark-gluon plasma (QGP) in heavy-ion collisions, resulting in collimated collections of hadrons known as jets. As a jet traverses and interacts with the QGP medium, it loses energy via collisional and radiative processes, known as jet quenching. The path-length dependence of jet quenching processes can be studied by measuring the azimuthal anisotropy of jet yields relative to the event plane, quantified by the second-order Fourier coefficient $v_2$. A finite jet $v_2$ is expected in mid-central heavy-ion collisions where a highly ellipsoidal QGP medium is formed, resulting in jets traversing in-plane interacting with less medium than those out-of-plane. In these proceedings, we report measurements of charged jet $v_2$ in isobar collisions spanning multiple jet resolutions. Ongoing work to use event shape engineering to more precisely control the path length of the initiating partons will also be discussed.