Top Director of Software Engineering Jobs in Chicago, IL

Leads software engineering teams modernizing legacy systems with cloud-native GCP technologies. Designs and develops .NET, C#, and Python applications; architects SQL and NoSQL data layers; manages Kubernetes infrastructure, CI/CD, testing, SDLC processes, and technical delivery. Provides code reviews, technical guidance, project estimation, stakeholder collaboration, monitoring, and continuous improvement across software development and DevOps initiatives.

Lead and scale software engineering teams building SaaS platforms. Set technical strategy, ensure best practices (architecture, CI/CD, security), drive delivery and KPIs, partner with Product and cross-functional leaders, and develop engineering talent while introducing AI/data capabilities to improve platform scalability, reliability, and business outcomes.

Leads the Platform Services organization, managing teams that build internal developer tooling, shared engineering services, golden-path templates, development environments, and AI-assisted development capabilities. Owns platform strategy, service reliability, security, adoption, productivity measurement, and consolidation of duplicated services. Partners with infrastructure and delivery teams, manages budgets and roadmaps, recruits and develops engineering leaders, and drives organizational change and engineering excellence.

Leads software development, QA, and DevOps for a digital insurance platform. Owns engineering roadmaps, delivery governance, architecture, code quality, security, testing, release reliability, and operational improvement. Manages and develops a small engineering team, partners with product and business stakeholders, evaluates technical risks, and guides responsible AI-assisted development. The role requires hands-on technical judgment across modern application architecture, Azure cloud services, CI/CD, automated testing, monitoring, and secure software delivery.

Leads a 40-person distributed systems engineering organization responsible for Elasticsearch scalability, performance, resilience, architecture, and Serverless capabilities. Develops long-term strategy, oversees complex cross-team initiatives, manages engineering managers and senior technical leaders, drives hiring and organizational planning, resolves critical operational issues, and communicates priorities to executives. Requires deep distributed systems expertise, large-scale software engineering experience, strong operational judgment, and proven organizational leadership.

Leads strategic software engineering initiatives within PwC’s Tax practice, overseeing application design, coding, testing, architecture, integration, and delivery. Drives digital transformation, develops scalable solutions using .NET, Java, Python, and Azure, and applies CI/CD and ATDD practices. The Director also manages client and executive stakeholders, identifies software product opportunities, ensures technical compliance, promotes innovation, and mentors software engineering leaders.

Leads a hands-on software engineering organization developing AI-enabled legal automation platforms. Responsibilities include setting technical direction, reviewing architecture and code, owning delivery and platform reliability, managing distributed teams, translating legal workflow requirements into scalable systems, and partnering with product, legal operations, executives, vendors, and clients. The role requires oversight of multi-tenant security, AI capabilities, Agile delivery, hiring, mentoring, and engineering quality.

Leads the software engineering organization responsible for scalable, reliable applications and systems integrating hardware, embedded software, edge computing, cloud infrastructure, and machine learning. Sets technical strategy, develops engineering leaders, drives product delivery, establishes engineering standards, and ensures operational excellence across national-scale deployments. Partners with Product, Deployment, Data Science, and executive leadership to align roadmaps, resolve risks, and build high-performing distributed teams.

Leads multiple software engineering teams supporting claims and other technology areas. Responsibilities include hiring and mentoring staff, budgeting, roadmap planning, architecture, hands-on delivery, security and compliance, performance optimization, modernization, CI/CD, technical strategy, and executive communication. The role requires driving scalable distributed systems, cloud transformation, operational excellence, and adoption of engineering best practices.

Leads the technical vision, architecture, development, and delivery of FOS software products. Manages and scales engineering teams, drives modernization from legacy to modern technology stacks, oversees cloud, microservices, APIs, CI/CD, quality, security, and reliability practices, and collaborates with product and business stakeholders. The role also supports talent recruitment and development, compliance with SOC 2 requirements, disaster recovery planning, and continuous engineering improvement.

Leads software engineering strategy and modernization for Specialty Pharmacy, overseeing product design, development, testing, delivery, and operational efficiency. Manages distributed engineering and change management teams, including hiring, coaching, performance management, and career development. Partners with business, product, and technology leaders to execute roadmaps, drive innovation, improve quality and time to market, and develop scalable cloud-based solutions using microservices, containerization, and AI technologies.

Leads the hands-on development and scaling of Oasis’s healthcare software platform. Responsibilities include architecture, production coding, AWS infrastructure, DevSecOps, AI-native workflows, external system integrations, reliability, observability, compliance, roadmap execution, and recruiting a high-performing engineering team. The role begins primarily as an individual contributor and evolves into player-coach leadership while delivering patient- and provider-facing applications.

Lead technical strategy for a 50–150+ engineer organization, establish architecture and engineering standards, drive delivery, and partner with executives on technology investments. Embed production-grade generative AI, LLMs, agentic workflows, and ML automation into engineering. Own AI platforms, distributed systems, cloud-native backend architecture, modernization initiatives, microservices migrations, and engineering transformation while ensuring scalable, reliable outcomes.

The Director of Software Engineering will lead the development of a comprehensive software system for the construction industry, ensuring successful technology delivery and communication with various stakeholders.

Lead a team of 10 engineers to architect and develop Node.js and Salesforce solutions, improving delivery schedules and performance metrics.

You will lead engineering teams, develop managers, hire staff, drive quality, and ensure disciplined processes while representing products to stakeholders.

Lead delivery for the Nebula SaaS platform: run planning, sprint execution, release management, and reliability at scale. Drive cloud platform and architecture modernization, move AI features from prototype to production, hire and develop engineering leaders, and own budget, headcount, and cross-functional partnerships.

Lead delivery for a cloud-based eDiscovery SaaS platform, owning roadmap execution, platform scalability, reliability, AI feature productionization, org design, hiring and development of engineering managers, budget and vendor management, and cross-functional partnership with Product and senior leadership.

Lead platform engineering teams to design, build, operate, and run OCI-native services for IoT and Connected Devices. Own service reliability, architecture, releases, incident response, KPIs, talent development, and cross-functional delivery of scalable, production-grade cloud services.

Lead and scale a ~50-engineer organization for Transitions of Care. Define engineering strategy and architecture, partner with product and stakeholders, coach managers, drive hiring and operational excellence, and support AI-driven, cloud-based platform delivery.

Lead an engineering domain (Consumer, B2B, or Backend), owning technical direction, delivery, system health, architecture, and team development. Translate business needs to technical plans, manage cross-team dependencies, ensure production readiness and incident response, and hire and mentor engineers to deliver scalable, reliable software.

Lead and scale full-stack engineering teams for Yahoo Mail; define engineering vision and roadmap; drive AI-native development and AI transformation using Generative AI/LLMs and agents; partner with Product, Design, and Data Science to deliver scalable cloud-native mobile and web experiences; hire, mentor, and retain engineering talent while guiding architecture, technical reviews, and platform modernization.