Technical Project Manager – TCC
Employer: Webhead (Web-Hed Technologies, LLC) Client: Education Service Center, Region 20 (ESC-20) Location: San Antonio, Texas – On-site at client location Employment Type: Full-time, W-2, contract-based assignment Initial Assignment: 12 months, with potential for renewal Annual Base Salary: $90,000–$96,000, commensurate with qualifications and experience Worksite: Hybrid, three days in the office, two days work from home. Reports To: Designated Client Administrator, with Webhead management oversight Position Summary osition Summary Webhead is seeking an experienced Technical Project Manager to support the modernization and continued operation of the ASCENDER product suite for Education Service Center, Region 20 (ESC-20). This highly collaborative, client-facing role will serve as the primary liaison between ESC-20 leadership, its internal technical and operational teams, and an external software development partner. The Technical Project Manager will bridge traditional operational practices with modern software development methodologies, ensuring that modernization initiatives respect existing business requirements while advancing the organization's digital transformation objectives. The successful candidate must demonstrate strong stakeholder management, diplomacy, technical understanding, and the ability to facilitate alignment among teams with different working styles, priorities, and levels of technical maturity. Beyond managing project schedules and deliverables, the TPM will support organizational change, encourage collaboration, manage competing expectations, and help translate executive priorities into measurable improvements in technology delivery, customer experience, and opportunities for growth across the education community served by ESC-20. Position Duration and Work Location This is a full-time W-2 employment opportunity with Webhead supporting a client engagement at ESC-20 in San Antonio, Texas. The initial client assignment is expected to last 12 months, with the possibility of renewal based on client requirements, contract funding, performance, and continued business needs. Renewal is not guaranteed. The selected candidate will work on-site at the designated client location and must be able to comply with applicable client workplace policies, schedules, and security requirements. Key ResponsibilitiesTechnical Project Management Develop and maintain integrated project plans, schedules, milestones, budgets, and deliverables. Coordinate multiple workstreams involving software development, modernization, and ongoing application operations. Monitor project execution, dependencies, risks, resource utilization, and delivery performance. Maintain project documentation, status reports, risk registers, and action items. Ensure project activities remain aligned with approved scope, schedules, and contractual requirements. Provide regular project updates and recommendations to ESC-20 leadership and Webhead management, as appropriate. Software Modernization and Technical Coordination Coordinate modernization initiatives involving legacy application architecture, system integration, data migration, and cloud technologies. Conduct and facilitate business process and technical gap analyses between existing ASCENDER workflows and proposed modernized solutions. Translate business requirements into actionable user stories, technical acceptance criteria, and implementation plans. Coordinate phased modernization activities, testing, deployment planning, and legacy system transitions. Monitor technical debt and support prioritization of improvements to system reliability, security, and maintainability. Help ensure existing application services remain operational throughout modernization efforts. Agile Delivery and Software Development Lifecycle Facilitate Agile ceremonies, including sprint planning, backlog refinement, sprint reviews, and retrospectives. Coordinate software development activities across internal teams and external technology partners. Monitor sprint progress, velocity, blockers, defects, and delivery quality. Coordinate release schedules, CI/CD activities, and deployment readiness with technical teams. Track software testing, defect resolution, and acceptance criteria. Promote consistent software development and project delivery practices. Vendor and Contract Management Serve as a primary coordination point for external software development partners and technology vendors. Track vendor deliverables against Statements of Work (SOWs), schedules, and contractual requirements. Monitor vendor performance, delivery quality, and service commitments. Coordinate resolution of vendor-related risks, dependencies, and issues. Support change control, scope management, and deliverable acceptance processes. Maintain visibility into vendor responsibilities and project dependencies. Application Operations and Performance Coordinate ongoing operational support for the ASCENDER product suite. Monitor application availability, performance, and service metrics. Track Service Level Agreements (SLAs) and Service Level Objectives (SLOs). Coordinate operational issues, incident resolution, and technical improvements with responsible teams. Help minimize service disruptions during modernization and release activities. Support continuous improvement in application reliability and operational processes. Stakeholder Engagement and Communication Maintain effective working relationships with ESC-20 leadership, Center staff, regional education clients, technical teams, and external partners. Facilitate project meetings, stakeholder reviews, and technical planning sessions. Communicate technical risks, dependencies, and architectural considerations in clear business terms. Manage stakeholder expectations regarding schedules, scope, deliverables, and operational impacts. Provide timely reporting and recommendations to support informed decisions. Promote collaboration and accountability across participating teams. Budget and Resource Management Track project expenditures, vendor costs, resource allocations, and cloud infrastructure expenses. Assist with project budgets, forecasts, and cost estimates. Identify potential cost overruns, resource constraints, and opportunities for improvement. Maintain accurate project documentation and supporting records. Ensure project-related recommendations comply with applicable ESC-20 policies and funding requirements.
Required Qualifications
Minimum three years of technical project management experience involving enterprise software development, application modernization, or IT operations. Bachelor's degree in Computer Science, Information Systems, Business, Project Management, or a related field preferred. Demonstrated experience coordinating software development teams and external technology vendors. Strong understanding of Agile methodologies and the Software Development Life Cycle (SDLC). Experience managing complex projects involving multiple stakeholders, technical dependencies, and contractual deliverables. Experience with business process analysis, requirements gathering, and technical gap assessments. Working knowledge of modern software architectures, APIs, system integration, and cloud environments. Familiarity with CI/CD practices, release management, and software quality assurance. Experience tracking SOWs, SLAs, vendor performance, and technical deliverables. Strong organizational, analytical, written communication, and stakeholder management skills. Proficiency with project management and collaboration tools, reporting applications, and Microsoft Office. Project Management Professional (PMP) and/or Certified ScrumMaster (CSM) certification required. Exceptions to qualification requirements may be considered for candidates demonstrating exemplary relevant experience, training, and a record of successful project delivery, consistent with client requirements.
Preferred Qualifications
Five or more years of experience managing enterprise software development or modernization projects. Experience with education-sector technology, public-sector systems, or enterprise administrative software. Familiarity with ERP, finance, payroll, human resources, or student information systems. Experience coordinating legacy-to-cloud modernization initiatives. Experience managing geographically distributed development teams and multiple technology vendors. Familiarity with DevOps, automated testing, and cloud cost management. Experience supporting phased modernization while maintaining production operations. Core Competencies Technical project leadership and accountability. Strong organizational and time management skills. Ability to manage multiple priorities and technical workstreams. Excellent written, verbal, and executive-level communication. Analytical thinking and practical problem-solving. Ability to influence teams and vendors without direct supervisory authority. Effective facilitation, negotiation, and conflict resolution. Customer service and stakeholder relationship management. Adaptability and sound judgment in changing technical environments. Professionalism and discretion when handling confidential information. Expected Outcomes The Technical Project Manager will be expected to: Maintain an integrated delivery plan covering ASCENDER operations and modernization initiatives. Provide accurate reporting on project schedules, milestones, budgets, risks, and vendor performance. Coordinate software releases and modernization activities with minimal operational disruption. Maintain visibility into technical debt, system performance, and modernization dependencies. Ensure vendor deliverables are reviewed against contractual requirements and acceptance criteria. Support effective communication and alignment among ESC-20 leadership, clients, and technical partners. Identify operational improvements and opportunities that support continued development of TCC products and services. Supervision and Work Requirements This position has no direct staff supervisory responsibility but requires coordination across internal teams, external vendors, and client stakeholders. The selected candidate must be able to work independently, manage competing priorities, and maintain professional communication in a dynamic technical environment. The role may require occasional extended or irregular hours, regional travel, and limited statewide or national travel. Candidates must be able to perform standard office and computer-based responsibilities and comply with applicable client policies, confidentiality requirements, and workplace standards. Compensation and Employment Terms Annual Base Salary: $90,000–$96,000, based on qualifications and relevant experience. Employment Classification: Full-time, W-2 employee of Webhead. Assignment Duration: Initial 12-month client engagement, with potential for renewal. Any extension is contingent upon client requirements, continued contract funding, performance, and business needs. Work Location: On-site at ESC-20's designated client location in San Antonio, Texas. Equal Employment Opportunity: Webhead is an equal opportunity employer. Employment decisions are made based on qualifications, merit, and business needs, consistent with applicable law. Pay: $90,000.00 - $96,000.00 per year
Benefits
Dental insurance Health insurance Health savings account Life insurance Paid time off Vision insurance Application Question(s): Stakeholder Alignment and Change Management. Describe a project where you had to align a traditional internal IT or operations team with an external development team using modern Agile practices. How did you address resistance to change, manage competing expectations, and build collaboration? Enterprise Software Modernization. Describe your experience managing enterprise software modernization while maintaining existing operations. How did you coordinate technical r Employment Requirements. Are you willing to accept a full-time W-2 position with Webhead, working on-site at ESC-20 in San Antonio for an initial 12-month assignment, with potential renewal, at an annual base salary of $90,000–$96,000? Yes No Work Location: Hybrid remote in San Antonio, TX 78208