  We present spatially resolved Keck Cosmic Web Imager stellar spectroscopy of
the Virgo cluster dwarf galaxies VCC 9 and VCC 1448. These galaxies have
similar stellar masses and large half-light radii but very different globular
cluster (GC) system richness ($\sim$25 vs. $\sim$99 GCs). Using the KCWI data,
we spectroscopically confirm 10 GCs associated with VCC 1448 and one GC
associated with VCC 9. We make two measurements of dynamical mass for VCC 1448
based on the stellar and GC velocities respectively. VCC 1448's mass
measurements suggest that it resides in a halo in better agreement with the
expectation of the stellar mass -- halo mass relationship than the expectation
from its large GC counts. For VCC 9, the dynamical mass we measure agrees with
the expected halo mass from both relationships. We compare VCC 1448 and VCC 9
to the GC-rich galaxy Dragonfly 44 ($\sim74$ GCs), which is similar in size but
has $\sim 1$ dex less stellar mass than either Virgo galaxy. In dynamical mass
-- GC number space, Dragonfly 44 and VCC 1448 exhibit richer GC systems given
their dynamical mass than that of VCC 9 and other `normal' galaxies. We also
place the galaxies in kinematics -- ellipticity space finding evidence of an
anticorrelation between rotational support and the fraction of a galaxy's
stellar mass in its GC system. i.e., VCC 9 is more rotationally supported than
VCC 1448, which is more rotationally supported than Dragonfly 44. This trend
may be expected if a galaxy's GC content depends on its natal gas properties at
formation.
