Software Delivery Lead (Senior)

DecisionPoint | Cortek•Chicago, IL

2d•Remote

About The Position

DecisionPoint seeks a senior Software Delivery Lead to direct software architecture, secure engineering, technical delivery, and release readiness for the USMEPCOM ENLIST program. The role provides technical and delivery leadership across multiple Agile teams responsible for designing, developing, integrating, testing, modernizing, deploying, and sustaining secure enterprise software. The Lead establishes technical direction, facilitates architecture and design reviews, manages cross-team dependencies, and ensures software increments meet approved functional, security, quality, configuration, documentation, and operational-readiness requirements. The role coordinates delivery from requirements development through production deployment and post-release validation. The Lead works closely with Government product and mission stakeholders, architects, developers, testers, cybersecurity personnel, configuration managers, infrastructure and cloud engineers, operations teams, trainers, and program leadership. The position is remote, with Chicago-area candidates preferred. Occasional travel or after-hours support may be required for planning sessions, release activities, production deployments, or critical incident response. Applicants acknowledge and consent to having their resumes included in an active competitive government contract bid.

Requirements

Active Secret clearance or higher.
Bachelor’s degree in computer science, information technology, software engineering, or a related field, or equivalent professional experience where permitted by the applicable labor category.
At least 10 years of relevant experience in software engineering, systems engineering, software architecture, technical delivery, application development, or a related discipline.
Experience managing or coordinating multiple Agile software-development teams.
Experience leading software delivery for Federal programs or customers.
Experience leading software architecture, system design, technical reviews, secure engineering, and release-readiness activities.
Experience directing software delivery across requirements, design, development, integration, testing, deployment, and sustainment.
Experience applying Agile, DevSecOps, configuration-management, and secure software-development practices.
Experience managing cross-team dependencies, technical risks, delivery schedules, release criteria, and stakeholder expectations.
Experience coordinating software-development, testing, cybersecurity, infrastructure, cloud, operations, and Government teams.
Experience evaluating test results, defects, security findings, documentation, deployment plans, and rollback readiness before release.
Experience developing or reviewing architecture, system-design, interface, requirements-traceability, or release documents, or comparable technical artifacts.
Ability to translate complex technical information into clear recommendations, briefings, status reports, and delivery decisions.
Strong leadership, facilitation, communication, analytical, organizational, and technical problem-solving skills.

Nice To Haves

Project Management Professional certification.
PMI Agile Certified Practitioner certification.
Certified ScrumMaster, Advanced Certified ScrumMaster, or Certified Scrum Professional certification.
SAFe Agilist, Release Train Engineer, or comparable scaled-Agile certification.
Certified Scrum Product Owner or comparable product-management certification.
DevSecOps, secure software-development, cloud, architecture, or systems-engineering certification.
ITIL v4 Foundation or higher certification.
Experience leading software delivery within Department of Defense environments.
Experience with Federal and DoD software, cybersecurity, accessibility, configuration-management, and documentation standards.
Experience managing several concurrent releases, products, or technical workstreams.
Experience with automated build, test, security-scanning, deployment, and release pipelines.
Experience supporting cloud-native, containerized, microservices, API-based, data-intensive, or hybrid enterprise solutions.
Experience supporting production deployment, operational transition, and post-release stabilization.
Experience conducting technical trade studies and developing concepts of operations or rough-order-of-magnitude estimates.

Responsibilities

Lead technical delivery across multiple Agile software-development teams.
Establish and communicate software architecture, engineering, integration, testing, deployment, and release expectations.
Facilitate architecture, system-design, interface, code-quality, security, and release-readiness reviews.
Ensure solutions are secure, scalable, extensible, supportable, testable, and aligned with current and target enterprise architectures, validated requirements, approved baselines, Government standards, and operational priorities.
Identify architectural risks, technical debt, integration concerns, capacity limitations, and operational dependencies, and develop or oversee corrective plans.
Manage dependencies and technical decisions across software, data, infrastructure, cloud, network, cybersecurity, testing, training, and operations teams; document decisions, assumptions, constraints, and impacts.
Lead software engineering across requirements analysis, design, development, integration, verification, validation, deployment, and sustainment, applying software- and systems-engineering, Agile, DevSecOps, and secure-development practices.
Oversee requirements gathering, analysis, decomposition, estimation, prioritization, and documentation; ensure requirements are clear, actionable, measurable, testable, traceable, and sufficiently detailed.
Oversee technical user stories, acceptance criteria, traceability records, interface requirements, and system-design documentation.
Support trade studies involving commercial, Government, custom-developed, cloud, data, software, and infrastructure alternatives; develop or oversee technical recommendations, concepts of operations, architecture options, implementation approaches, and rough-order-of-magnitude estimates.
Direct the establishment and use of development, integration, test, staging, and other preproduction environments; coordinate availability, configuration, test data, tools, licenses, access, and dependencies while maintaining appropriate separation from operational environments.
Lead release and Sprint planning across multiple Agile teams, including recommendations on frequency, duration, sequencing, dependencies, and milestones for Government approval.
Coordinate team structures, environments, delivery methods, mission interaction, and technical processes; facilitate or oversee Sprint planning, backlog refinement, daily coordination, reviews, demonstrations, and retrospectives.
Ensure Sprint backlogs reflect approved priorities, estimated effort, available resources, dependencies, and delivery risks; provide or oversee weekly progress updates and demonstrations for Government stakeholders.
Track planned, completed, added, deferred, blocked, and accepted work; document lessons learned, metrics, accomplishments, delivery concerns, Development Sprint Plans, and Sprint Summary Reports.
Oversee configuration management for software, scripts, configuration files, interfaces, build assets, deployment assets, and related baseline components; ensure changes are documented against baselines and recorded in the Configuration Management Database as required.
Coordinate configuration- and change-control activities, ensuring configuration items, implementation status, issues, approvals, and baseline changes are traceable.
Ensure source code, configuration files, scripts, build instructions, installation procedures, dependencies, version descriptions, and release documentation are complete; document software modules, versions, dependencies, and known defects.
Ensure build, installation, deployment, rollback, and recovery procedures are documented and repeatable.
Establish and enforce release-readiness criteria; verify completion of required design, code, integration, functional, regression, interface, security, performance, load, accessibility, and operational testing.
Verify traceability, test results, defect disposition, security findings, documentation, training, configuration control, deployment procedures, and rollback readiness; coordinate go/no-go recommendations with Government stakeholders and technical teams.
Ensure unresolved defects, risks, exceptions, and limitations are documented and communicated before release approval; coordinate operational deployments and oversee post-release verification and stabilization.
Maintain feedback loops among development, testing, operations, security, mission owners, and end users; assess and improve feedback, integration, testing, deployment, and release-management practices.
Coordinate urgent software security fixes and ensure they are prioritized, tested, documented, and released; evaluate and document security impacts throughout the software-development lifecycle.
Coordinate with cybersecurity personnel on secure design, vulnerability remediation, security testing, authorization evidence, and production approval; ensure compliance with applicable Federal and DoD standards, including approved DISA Security Technical Implementation Guides.
Promote automated builds, code control, regression testing, security scanning, integration testing, and deployment automation.
Monitor delivery performance, release predictability, defect trends, security issues, technical debt, rework, dependencies, and team capacity; identify systemic problems and lead corrective and continual-improvement actions.
Mentor architects, technical leads, developers, testers, and Agile delivery personnel; facilitate resolution of complex technical disagreements and cross-team barriers.
Support technical briefings, program reviews, release reviews, demonstrations, audits, and Government decision meetings; provide status, schedule, accomplishments, risks, issues, dependencies, corrective actions, and release outlook for program reporting.