Abstract We present photometric and spectroscopic observations of SN 2020bio, a double-peaked Type IIb supernova (SN) discovered within a day of explosion, primarily obtained by Las Cumbres Observatory and Swift. SN 2020bio displays a rapid and long-lasting initial decline throughout the first week of its light curve, similarly to other well-studied Type IIb SNe. This early-time emission is thought to originate from the cooling of the extended outer hydrogen-rich (H-rich) envelope of the progenitor star that is shock heated by the SN explosion. We compare SN 2020bio to a sample of other double-peaked Type IIb SNe in order to investigate its progenitor properties. Analytical model fits to the early-time emission give progenitor radius (≈100–1500 R _⊙) and H-rich envelope mass (≈0.01–0.5 M _⊙) estimates that are consistent with other Type IIb SNe. However, SN 2020bio displays several peculiarities, including (1) weak H spectral features indicating a greater amount of mass loss than other Type IIb progenitors; (2) an underluminous secondary light-curve peak that implies a small amount of synthesized ⁵⁶Ni (M _Ni ≈0.02 M _⊙); and (3) low-luminosity nebular [O i] and interaction-powered nebular features. These observations are more consistent with a lower-mass progenitor (M _ZAMS ≈ 12 M _⊙) that was stripped of most of its H-rich envelope before exploding. This study adds to the growing diversity in the observed properties of Type IIb SNe and their progenitors.