Sequence-defined macromolecules have gained increasing interest due to the recognition of the sequence-structure-property relationship. Over the past decade, the Alabi research group has achieved the novel design and synthesis of oligothioetheramides (oligoTEA). These oligomers are highly valued for their demonstrated biological applications as antimicrobial and cell-delivery agents. Synthesized via alternating thiol-Michael addition and thiol-ene reactions of N-allylacrylamide and dithiol monomers covalently bound to a fluorous support, this synthetic approach is rapid and efficient. However, intrinsic to the use of fluorous tags, rigorous purification and scalability pose as major production challenges. As a result, in this work, we focus on the design of a solid-phase synthesis (SPS) approach for oligoTEA production as a facile, economical alternative. Specifically, this work explores the use of various resins and linkers, and elucidates the design of a submonomer approach using three key reaction classes in an iterative fashion, to achieve a full oligomeric sequence, namely: i. thiol-Michael addition, ii. reductive amination, and iii. acylation. In compatibility with this approach, this work further explores the use of various commercially available primary amines and dithiol building blocks and cleavage conditions to achieve chain extension and customizability to the final oligoTEA composition.