We report on the validation of two planets orbiting the nearby (36 pc) M2 dwarf TOI-1266 observed by the TESS mission. This system is one of a few M dwarf multiplanet systems with close-in planets where the inner planet is substantially larger than the outer planet. The inner planet is sub-Neptune-sized (R = 2.46 ± 0.08 R⊕) with an orbital period of 10.9 days, while the outer planet has a radius of 1.67-0.11+0.09 R⊕ and resides in the exoplanet radius Valley-the transition region between rocky and gaseous planets. With an orbital period of 18.8 days, the outer planet receives an insolation flux of 2.4 times that of Earth, similar to the insolation of Venus. Using precision near-infrared radial velocities with the Habitable-zone Planet Finder Spectrograph, we place upper mass limits of 15.9 and 6.4 M⊕ at 95% confidence for the inner and outer planet, respectively. A more precise mass constraint of both planets, achievable with current radial velocity instruments given the host star brightness (V = 12.9, J = 9.7), will yield further insights into the dominant processes sculpting the exoplanet radius valley.