Technical Lead Jobs in Chicago, IL

RRD provides marketing, packaging, print, and business services to the world’s most respected brands. The company’s proprietary technology, advanced data analytics, and expertise fuel organizational decision-making from strategy through execution, delivering sustainable solutions with the lowest possible environmental impact. Global organizations and regulated industries trust RRD to reduce complexity and drive audience connections across the entire customer journey.

Join Williams Lea, an RRD Company, in transforming legal and business support through AiVA—our proprietary AI orchestration platform. Working in high-energy, bootcamp-style pods directly alongside top global law firms, our teams rapidly design, test, and deploy cutting-edge AI workflows that power business-critical operations. If you thrive on fast-paced iteration and want to redefine the future of professional services, apply today to join our AiVA Talent Pipeline and shape next-generation AI solutions.

The Technical Lead is the senior architect and technical role in AiVA engagements. Once a client engagement is signed, this role owns the architectural pattern, the integration approach, and the technical quality of everything the AiVA pod builds. The role provides architectural direction, technical review, and escalation resolution. Accountable not for building skills but for the technical soundness of what gets built and liaising with the platform engineering team where necessary.

Overall Aims:

• Technical architecture that supports the engagement outcomes: scalable, maintainable, secure, and defensible under client technical scrutiny.
• Consistent architectural pattern across the assigned pods.
• Sound technical decisions within the engagement, with clear architectural guidance to the AI Workflow Engineers.
• Technical soundness that supports both immediate engagement outcomes and long-term client platform investment.
• Architectural clarity that lets AI Workflow Engineers build at pace without technical rework.

Key Responsibilities:

Architecture & Technical Direction

• Define the architectural pattern for each engagement: skill decomposition, tool orchestration, data flow, integration approach, and deployment model.
• Ensure all architecture patterns are in line with security best practices and with client requirements. Designing client specific guardrails as appropriate
• Review and sign off on AI Workflow Engineer builds against the agreed architectural pattern.
• Own integration architecture with client systems: authentication, data ingress, downstream deployment, and monitoring.
• Make platform-versus-custom decisions with the Head of Platform Engineering and Product where the engagement stretches platform capability.
• Design and document the target technical state, transition plan, and operational readiness criteria for handover to sustained delivery.
• Own the technical risk register for the engagement; surface and escalate technical risks early to the Delivery Principal.

Engagement Execution

• Work across multiple client engagements as the Technical Lead.
• Partner with the Delivery Principal on scope, timeline, and technical feasibility decisions.
• Present technical architecture to senior client stakeholders including Chief Technology Officers, technical partners, information security and enterprise architects.
• Specify all integrations and work with the platform development team to deliver integrations, connectivity, and upstream system integration.
• Guide the AI Workflow Engineer on architectural choices, prompt strategy, and evaluation design without taking over the build.
• Contribute technical input to commercial conversations; flag technical scope creep and platform-limit risks to the Delivery Principal and Client Partner early.

Technical Leadership

• Develop and mentor AI Workflow Engineers and Integration Engineers through the engagement; provide structured technical input to functional managers on capability development.
  

Continuous Improvement & Standards

• Contribute architectural patterns and technical playbooks to the Technical Lead community; refine standards based on engagement experience.
• Mentor newer Technical Leads as the function scales; contribute to capability development across the cohort.
• Ensure compliance with client requirements, data protection, security standards, and AiVA platform architectural standards across the engagement.

• Bachelor’s degree in Computer Science, Engineering, or a related technical field, or equivalent experience.
• 8+ years of software engineering, cloud architecture, or enterprise integration experience.
• Track record of leading complex technical architecture on client-facing delivery engagements; comfortable presenting to senior technical audiences.
• Demonstrated experience with AI or automation platforms at enterprise scale; familiarity with agent frameworks, LLM APIs, and orchestration patterns.
• Cloud certification (Azure preferred, AWS, GCP relevant) or equivalent demonstrated cloud architecture experience.
• Strong integration engineering background: authentication, data pipelines, deployment infrastructure, and monitoring.
• Comfortable working across geographies and time zones (US, UK, EMEA clients).
• Experience in legal, professional services, or knowledge-worker environments preferred; not required.

Personal Attributes

• Senior technical presence; comfortable in client-facing rooms with senior technical stakeholders (Chief Technology Officers, enterprise architects, technical partners).
• Architect mindset with hands-on origins; can direct technical work without needing to do it, and knows when to intervene versus when to let a builder solve it.
• Comfortable operating across multiple engagements simultaneously; manages competing priorities without dropping either.
• Deep interest in AI-enabled automation architecture; keeps up with the platform, integration patterns, and the wider AI engineering community.
• Resilient under client technical pressure; defends design choices constructively rather than defensively.
• Continuous learner; adapts architectural patterns as the AiVA platform evolves.
• Quality-first orientation; treats architectural clarity, evaluation, and observability as first-class outcomes.
• Comfortable working across geographies (US, UK, India) and across sectors including legal and professional services.

RRD's current salary range for this role is $129,500 to $207,200 / year. The salary range may be adjusted based on the applicable geographic location of the hired employee, and the range may change in the future. At RRD, it is not typical for an individual to be hired at or near the top of the range for their role and compensation decisions may vary based upon, but not limited to education, skills, experience, proficiency, performance, shift and location. Depending on the role, in addition to base salary, the total compensation package may also include participation in a bonus, commission or incentive program. RRD’s benefit offerings include medical, dental, and vision coverage, paid time off, disability insurance, 401(k) with company match, life insurance and other voluntary supplemental insurance coverages, plus parental leave, adoption assistance, tuition assistance and employer/partner discounts.

RRD is an Equal Opportunity Employer, including disability/veterans

At RRD, we value innovation, authenticity, and integrity. To uphold the security and fairness of our hiring process, we ask that candidates refrain from using AI tools during interviews to ensure an authentic and secure experience. We appreciate your cooperation as we work to maintain a transparent and equitable hiring process.

All employment offers are contingent upon the successful completion of both a pre-employment background and drug screen.