We consider generation of dark matter mass via radiative electroweak symmetry breaking in an extension of the conformal Standard Model containing a singlet scalar field with a Higgs portal interaction. Generating the mass from a sequential process of radiative electroweak symmetry breaking followed by a conventional Higgs mechanism can account for less than 35% of the cosmological dark matter abundance for dark matter mass $M_s>80 GeV$. However in a dynamical approach where both Higgs and scalar singlet masses are generated via radiative electroweak symmetry breaking we obtain much higher levels of dark matter abundance. At one-loop level we find abundances of 10%--100% with $106 GeV<M_s<120 GeV$. However, when the higher-order effects needed for consistency with a $125 GeV$ Higgs mass are estimated, the abundance becomes 10%--80% for $80 GeV<M_s<96 GeV$, representing a significant decrease in the dark matter mass. The dynamical approach also predicts a small scalar-singlet self-coupling, providing a natural explanation for the astrophysical observations that place upper bounds on dark matter self-interaction. The predictions in all three approaches are within the $M_s>80 GeV$ detection region of the next generation XENON experiment.