The CTO must build durable working relationships across Operations, Engineering, Maintenance & Construction (EM&C), System Safety, Transit Police, Legal, Human Resources, Customer Experience, and the rest of the Finance Division - and externally with the SEPTA Board, Commonwealth stakeholders such as PennDOT, Federal stakeholders such as FTA, and local stakeholders such as the City of Philadelphia and the four suburban counties, DVRPC, and technology and systems-integration partners. Lead assessment, disposition, and migration of legacy on-premises workloads - ERP/financials, asset and maintenance management (EAM), scheduling and workforce systems, CAD/AVL and operations data, and reporting platforms - using the appropriate rehost, replatform, refactor, or replace path for each.