Of the more than 3000 radio pulsars currently known, only ∼300 are in binary systems, and only five of these consist of young pulsars with massive nondegenerate companions. We present the discovery and initial timing, accomplished using the Canadian Hydrogen Intensity Mapping Experiment (CHIME) telescope, of the sixth such binary pulsar, PSR J2108+4516, a 0.577 s radio pulsar in a 269 day orbit of eccentricity 0.09 with a companion of minimum mass 11 M ⊙. Notably, the pulsar undergoes periods of substantial eclipse, disappearing from the CHIME 400–800 MHz observing band for a large fraction of its orbit, and displays significant dispersion measure and scattering variations throughout its orbit, pointing to the possibility of a circumstellar disk or very dense stellar wind associated with the companion star. Subarcsecond resolution imaging with the Karl G. Jansky Very Large Array unambiguously demonstrates that the companion is a bright, V ≃ 11 OBe star, EM* UHA 138, located at a distance of 3.26(14) kpc. Archival optical observations of EM* UHA 138 approximately suggest a companion mass ranging from 17.5 M ⊙ < M c < 23 M ⊙, in turn constraining the orbital inclination angle to 50.°3 ≲ i ≲ 58.°3. With further multiwavelength follow-up, PSR J2108+4516 promises to serve as another rare laboratory for the exploration of companion winds, circumstellar disks, and short-term evolution through extended-body orbital dynamics.