Commission Software Engineer Rotational Program Jobs in Chicago, IL

We're looking for a Lead Product Software Engineer - Cloud Operations to join InnovateHub, our startup-within-the-enterprise that co-designs AI solutions with customers across Wolters Kluwer's Tax and Accounting product portfolio. In this role you'll own the infrastructure foundations that power our AI products: designing cloud architecture, delivering Terraform-managed environments, building product and operational health reporting, and enabling development teams to ship with confidence.

InnovateHub operates with close collaboration between engineers, product managers, UX designers, and researchers. Engineers deeply understand business problems, product managers rapidly prototype ideas, and designers and researchers translate user needs into elegant, evidence-based solutions. We work in fast feedback cycles, obsess over customer value, and blur traditional role boundaries to focus on solving the right problems. We practice Agile and XP methodologies with weekly sprints, BDD/TDD practices, and pair programming with daily rotation to support high team cohesion and knowledge sharing.

This role is ideal for someone who bridges infrastructure and product engineering, equally comfortable writing Terraform modules, designing Azure architectures, and consulting with developers on observability and deployment patterns. You'll coordinate closely with Infrastructure Operations and Architecture teams while serving as the cloud operations anchor within InnovateHub.

Key Responsibilities:

Infrastructure Delivery & Architecture

• Own Terraform delivery for InnovateHub's Azure environments, authoring and maintaining infrastructure-as-code modules that are secure, repeatable, and compliant with SOC 2 and IRS 7216 requirements.
• Collaborate with Infrastructure Operations and Architecture and Product teams to design, review, and evolve cloud infrastructure, ensuring alignment with enterprise standards and cost while meeting the speed and flexibility InnovateHub requires.
• Design and implement Azure resource architectures (App Services, Functions, Cosmos DB, AI Services, Key Vault, networking) that support our AI product portfolio at scale

Product & Operational Health Reporting

• Build and own product and operational health dashboards using data sources such as Azure Monitor, Application Insights, and Log Analytics-giving the team and leadership clear visibility into system reliability, performance, and usage.
• Define and track SLIs/SLOs for InnovateHub products, establishing alerting strategies and incident response patterns that keep our services healthy.
• Translate telemetry and observability data into actionable insights that inform product decisions, capacity planning, and operational improvements.

Developer Enablement & Consultation

• Serve as the go-to cloud operations resource for InnovateHub developers-providing guidance, reusable templates, and hands-on consultation for infrastructure and deployment needs.
• Create and maintain infrastructure templates, CI/CD pipeline patterns, and deployment runbooks that accelerate developer self-service and reduce friction.
• Partner with developers during pair programming rotations to embed infrastructure best practices into the development workflow, including observability instrumentation, secure configuration, and cost optimization.

Cross-Team Collaboration

• Act as the liaison between InnovateHub and enterprise Infrastructure Operations and Architecture teams, ensuring cloud decisions are coordinated and knowledge flows in both directions.
• Work within InnovateHub's collaborative model where engineers understand business problems as deeply as technical solutions, partnering closely with product managers, UX, and research.
• Support cross-portfolio infrastructure needs, enabling other TAA teams to leverage patterns and platforms built by InnovateHub.

Requirements:

Technical Foundation:

• 5+ years building and operating cloud infrastructure (Azure strongly preferred)
• 2+ years hands-on experience with Terraform (or equivalent IaC tools) in production environments
• Strong proficiency with Azure PaaS services: App Services, Functions, Cosmos DB, Key Vault, Virtual Networks, Application Gateway, and Azure AI Services
• Deep experience with Azure Monitor, Application Insights, Log Analytics, and KQL for observability and health reporting
• Experience with CI/CD pipelines (Azure DevOps, GitHub Actions) including infrastructure deployment automation
• Experience with Agile/XP practices including TDD/BDD and pair programming
• Proficiency with AI coding tools (GitHub Copilot, Cursor, or similar) and regular use of GenAI utilities for development workflow

Technical Project Leadership:

• 3+ years leading infrastructure or platform engineering initiatives from design through production operation
• Experience working in startup-like environments or innovation teams
• Comfort working in collaborative, fast-paced Agile environments with weekly sprints and blurred (but aligned) role boundaries

Infrastructure & Operations Experience:

• Working knowledge of infrastructure security practices: network segmentation, managed identities, RBAC, secrets management, and compliance controls (SOC 2, IRS 7216 a plus)
• Experience defining SLIs/SLOs and building operational dashboards and alerting strategies
• Understanding of cost management and FinOps principles for Azure environments

Communication Skills:

Ability to explain infrastructure concepts to product-focused developers and non-technical stakeholders. Experience creating documentation, templates, and runbooks that enable self-service across teams.

Preferred Qualifications:

• Microsoft Azure AZ-104 (Azure Administrator) or AZ-305 (Azure Solutions Architect) certification is highly desired - our team values demonstrated Azure expertise and AI-102 certification is also a plus
• Experience with Azure Landing Zones, hub-spoke network topologies, or enterprise-scale Azure architectures
• Background in regulated or compliance-driven environments, particularly financial services or tax/accounting software
• Experience with containerization (Docker, AKS) and service mesh patterns
• Familiarity with AI/ML infrastructure needs: model serving, vector database operations, and RAG system infrastructure
• Experience with platform engineering, developer experience (DevEx) tooling, or internal developer platforms

We encourage applications from candidates with diverse backgrounds who have strong infrastructure skills, project leadership experience, and can adapt quickly to new challenges in a customer-focused, innovation-driven environment.

Our Culture:
At Wolters Kluwer, our core values-Focus on Customer Success, Make it Better, Aim High and Deliver, and Win as a Team-guide everything we do. We are committed to driving success for our customers by delivering innovative solutions that exceed expectations. We continually strive to improve our processes and products, aiming for excellence in all our efforts. Collaboration and teamwork are central to our culture, enabling us to achieve great results together.

To maintain a fair and genuine hiring process, we kindly ask that all candidates participate in interviews without the assistance of AI tools or external prompts. Our interview process is designed to assess your individual skills, experiences, and communication style. We value authenticity and want to ensure we're getting to know you-not a digital assistant. To help maintain this integrity, we ask to remove virtual backgrounds and include in-person interviews in our hiring process. Please note that use of AI-generated responses or third-party support during interviews will be grounds for disqualification from the recruitment process.

Applicants may be required to appear onsite at a Wolters Kluwer office as part of the recruitment process.

Compensation:

Compensation range listed is based on primary location of the position. Actual base salary offer is influenced by a wide array of factors including but not limited to skills, experience and actual hiring location. Your recruiter can share more information about the specific offer for the job location during the hiring process.

Wolters Kluwer offers a wide variety of competitive benefits and programs to help meet your needs and balance your work and personal life, including but not limited to: Medical, Dental, & Vision Plans, 401(k), FSA/HSA, Commuter Benefits, Tuition Assistance Plan, Vacation and Sick Time, and Paid Parental Leave. Full details of our benefits are available upon request.