Trainee Software Engineer Startup Jobs in Illinois

**This is a Hybrid role requiring 2 days a week in a Wolters Kluwer office**

We're looking for a Lead Product Software Engineer - AI to join InnovateHub, our startup-within-the-enterprise that co-designs AI solutions with customers across Wolters Kluwer's Tax and Accounting product portfolio. You'll develop cutting-edge AI features that transform how accounting professionals work, focusing on real customer problems rather than technology-first solutions.

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 adapts quickly to new technologies, communicates effectively across teams, thrives in collaborative environments, and is passionate about human-centric AI solutions that deliver real value to professionals.

Key Responsibilities:

Customer-Centric Product Development: Co-design AI solutions with customers, focusing on real problems rather than technology-first approaches. Build human-centric AI features that deliver measurable value in fast feedback cycles.

Cross-Portfolio Innovation: Work across TAA's product portfolio, enabling other teams while building AI solutions that can be applied to multiple products and customer segments.

Technical Leadership: Design and implement AI features using Python and modern frameworks. Build intelligent document processing, automated workflows, and AI-powered analytics with a focus on security, product experience, and scalability.

Close Collaboration: Work in InnovateHub's collaborative model where engineers understand business problems as deeply as technical solutions, partnering closely with product managers who prototype their own ideas.

Requirements:

Technical Foundation:

• 5+ years building software applications (experience with Python, JavaScript/TypeScript preferred)

• 1+ years hands-on experience with LLMs or AI systems (NLP preferred)

• Full-stack development capabilities

• Experience with Agile/XP practices including TDD/BDD and pair programming

• Proficiency with AI coding tools (GitHub Copilot, Cursor, or similar)

• Regular use of GenAI utilities (ChatGPT, Claude, etc.) for development workflow

Technical Project Leadership:

• 3+ years leading complex technical projects from inception to delivery

• 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

AI/ML Experience:

• Working knowledge of AI/ML frameworks (LangChain, Hugging Face, OpenAI APIs)

• Experience with vector databases and embeddings

• Understanding of prompt engineering and AI optimization

Communication Skills: Ability to explain technical concepts to non-technical stakeholders and drive adoption of new technologies across teams.

Preferred Qualifications:

• Microsoft Azure AI-102 certification is highly desired - our team is 100% certified and we value this demonstration of Azure AI expertise

• Experience with Azure AI services, advanced AI frameworks, or multi-modal AI systems

• Background in dynamic environments like startups, innovation teams, or product-focused companies that prioritize customer co-design and rapid value delivery

• Experience with document processing, financial data analysis, or B2B professional software

• Experience with MLOps, AI governance, or cross-portfolio AI implementations, particularly in regulated/compliance-driven environments

• Experience with RAG (Retrieval-Augmented Generation)

• Understanding of UX/UI

We encourage applications from candidates with diverse backgrounds who have strong technical 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.