Abstract The Transiting Exoplanet Survey Satellite (TESS) continues to increase dramatically the number of known transiting exoplanets, and is optimal for monitoring bright stars amenable to radial velocity (RV) and atmospheric follow-up observations. TOI-1386 is a solar-type (G5V) star that was detected via TESS photometry to exhibit transit signatures in three sectors with a period of 25.84 days. We conducted follow-up RV observations using Keck/High Resolution Echelle Spectrometer (HIRES) as part of the TESS–Keck Survey, collecting 64 RV measurements of TOI-1386 with the HIRES spectrograph over 2.5 yr. Our combined fit of the TOI-1386 photometry and RV data confirm the planetary nature of the detected TESS signal, and provide a mass and radius for planet b of 0.148 ± 0.019 M _J and 0.540 ± 0.017 R _J, respectively, marking TOI-1386 b as a warm sub-Saturn planet. Our RV data further reveal an additional outer companion, TOI-1386 c, with an estimated orbital period of 227.6 days and a minimum mass of 0.309 ± 0.038 M _J. The dynamical modeling of the system shows that the measured system architecture is long-term stable, although there may be substantial eccentricity oscillations of the inner planet due to the dynamical influence of the outer planet.