The theory of finite-rank perturbations allows for the determination of spectral information for broad classes of operators using the tools of analytic function theory. In this work, finite-rank perturbations are applied to powers of the derivative operator, providing a full account from self-adjoint boundary conditions to computing aspects of the operators' matrix-valued spectral measures. In particular, the support and weights of the Clark (spectral) measures are computed via the connection between matrix-valued contractive analytic functions and matrix-valued nonnegative measures through the Herglotz Representation Theorem. For several powers of the derivative operator, explicit expressions are included. While eigenfunctions and eigenvalues for these operators with fixed boundary conditions can often be computed using direct methods from ordinary differential equations, this approach provides a more complete picture of the spectral information.