We introduce an extended class of cross-Toeplitz operators which act between Fock–Segal–Bargmann spaces with different weights. It is natural to consider these operators in the framework of representation theory of the Heisenberg group. Our main technique is representation of cross-Toeplitz by two-sided relative convolutions from the Heisenberg group. In turn, two-sided convolutions are reduced to usual (one-sided) convolutions on the Heisenberg group of the doubled dimensionality. This allows us to utilise the powerful group-representation technique of coherent states, co- and contra-variant transforms, twisted convolutions, symplectic Fourier transform, etc. We discuss connections of (cross-)Toeplitz operators with pseudo-differential operators, localisation operators in time–frequency analysis, and characterisation of kernels in terms of ladder operators. The paper is written in a detailed and reasonably self-contained manner to be suitable as an introduction into group-theoretical methods in phase space and time–frequency operator theory.