• Director, Software Engineering

    Insight Global (Carol Stream, IL)


    Job Description

    A Client Communications Management (CCM) Firm is seeking a Director of Software Engineering to join their organization. The Director of Software Engineering will lead multiple software development teams to design, build, and deliver innovative, secure, and scalable solutions that support the print and digital platforms. This role combines deep technical expertise with strategic leadership to modernize engineering practices, integrate AI-powered development tools, and ensure the consistent delivery of high-quality software aligned with company objectives.

    Key Responsibilities

    • Lead and mentor software development teams, ensuring proper staffing, training, and performance management.

    • Oversee end-to-end software delivery processes, ensuring adherence to coding, testing, and deployment standards.

    • Define and execute the roadmap for AI-powered development tools, including prompt engineering strategies, tool integration, and developer onboarding.

    • Own the implementation, governance, and optimization of GitHub Copilot (and similar tools) across all engineering teams.

    • Develop and maintain reusable prompt templates that reinforce best practices, architectural consistency, and secure coding standards.

    • Partner with Architecture, DevOps, and Security teams to ensure AI-generated code aligns with OSGConnect’s technical, operational, and compliance frameworks.

    • Drive continuous improvement in code quality, system reliability, and delivery speed through automation and agile methodologies.

    • Oversee technology evaluations, proof of concepts, and adoption of modern frameworks and practices to enhance scalability and resilience.

    • Collaborate with product and business leaders to translate strategic goals into actionable technology roadmaps.

    • Foster a culture of innovation, accountability, and learning within the engineering organization.

     

    We are a company committed to creating diverse and inclusive environments where people can bring their full, authentic selves to work every day. We are an equal opportunity/affirmative action employer that believes everyone matters. Qualified candidates will receive consideration for employment regardless of their race, color, ethnicity, religion, sex (including pregnancy), sexual orientation, gender identity and expression, marital status, national origin, ancestry, genetic factors, age, disability, protected veteran status, military or uniformed service member status, or any other status or characteristic protected by applicable laws, regulations, and ordinances. If you need assistance and/or a reasonable accommodation due to a disability during the application or recruiting process, please send a request to [email protected] learn more about how we collect, keep, and process your private information, please review Insight Global's Workforce Privacy Policy: https://insightglobal.com/workforce-privacy-policy/.

    Skills and Requirements

    • Bachelor’s degree in Computer Science, Software Engineering, or a related technical discipline (Master’s preferred).

    • 8+ years of experience in software engineering, including 2–4 years in a leadership or architecture role.

    • Deep understanding of .NET development, Visual Studio, and modern SDLC workflows (Git, CI/CD pipelines, automated testing).

    • Demonstrated experience implementing or managing AI-assisted development tools (e.g., GitHub Copilot, Amazon CodeWhisperer, CodiumAI, Cursor, etc.).

    • Strong background in prompt engineering, code quality enforcement, and developer productivity tooling.

    • Familiarity with cloud-native development in AWS, including services such as CodeCatalyst, Bedrock, or SageMaker.

    • Excellent communication, problem-solving, and organizational skills with a collaborative leadership style. • Experience in the print and digital communications or customer communications management (CCM) industry.

    • Proven ability to drive transformation within a growing technology organization.

    • Knowledge of microservices architecture, API development, and containerization (Docker/Kubernetes).

    • Demonstrated success in scaling development teams and optimizing engineering performance metrics.

    • Knowledge of current AI techniques and components like RAG and MCP