Apprentice Complete Delivery Solutions Jobs in Chicago, IL

Reporting to the IT Solutions Delivery Manager, the IT Solutions Delivery Lead is pivotal in planning, designing, communicating, and executing high-impact IT initiatives that support firmwide transformation. These initiatives encompass core IT services such as Unified Communications, Microsoft platforms, Mobility, Infrastructure & Hosting, Marketing, Financial, and other business technology. The role requires close collaboration with cross-functional teams—including Product Management, Architecture, Engineering, and Technical Operations—as well as firm leadership to ensure strategic alignment and execution. Based on project size and complexity, the Lead may work independently or oversee a team of Delivery Analysts.

Partnering with the IT Project Manager, the IT Solutions Delivery Lead oversees end-to-end initiative implementation—from early planning and analysis through build, testing, launch, and post-deployment support. This includes risk identification and mitigation, documentation, and issue triage. A key focus of the role is guiding technical and portfolio teams to research, engineer, implement and maintain delivery solution frameworks throughout each project lifecycle. The ideal candidate brings broad technical and cross-functional expertise, enabling them to quickly adapt to new technologies and deliver solutions that enhance operational efficiency and integration across the Firm’s technology ecosystem.

Duties and Responsibilities:

• Analyze complex problems and translate them into clear, actionable goals and strategic plans.

• Collaborate with stakeholders to build and support compelling business cases, including analysis, process documentation, and action plans to ensure project success.

• Lead solution delivery by defining business requirements, providing technical guidance, creating actionable plans, and executing seamless implementation paths.

• Work with leadership and stakeholders to prioritize work based on business impact and strategic alignment.

• Leverage a deep understanding of user experience, particularly in a legal environment, to identify and address unique technical challenges.

• Partner with operational teams and IT Solutions Delivery Analysts to ensure technology initiatives are closely aligned with business objectives.

• Engage with external vendors to resolve product inquiries, conduct technology assessments, and participate in design and architecture reviews.

• Proactively identify unknowns and potential blind spots in technical implementations.

• Emphasize user experience and the quality of solutions over speed of delivery.

• Stay informed about emerging technologies and trends that support the firm’s long-term technology strategy.

• Manage pilot programs and firmwide rollouts of new technologies, ensuring readiness and effectiveness.

• Advise on project management implications throughout the initiative lifecycle, including strategy development, readiness assessment, training, and communication planning.

• Communicate technical and business concepts clearly and effectively to both technical and non-technical audiences across various levels of the organization.

Education and/or Experience: 

Required:

• A Bachelor’s degree

• A minimum of 7 years of experience leading complex, high-impact, cross-functional technology implementations.

• A minimum of 7 years of experience in project management, business analysis leadership, or implementation leadership for enterprise-level technology initiatives.

• Experience delivering large-scale, high-user-impact solutions—whether in software, infrastructure, or hybrid implementations.

• A proven track record of contributing to the improvement of processes, methodologies, and delivery frameworks.

• Strong knowledge and hands-on experience with project management principles, tools, and methodologies (e.g., Smartsheet, Asana, Microsoft Project).

• Demonstrated strategic and creative problem-solving abilities, including the design of efficient systems, performance metrics, and decision-making tools.

• Exceptional collaboration and influencing capabilities

• Experience preparing and delivering executive-level presentations.

Preferred:

• Master’s Degree

• Consulting experience

• Legal industry experience

• Professional services experience

Other Skills and Abilities:

The following will also be required of the successful candidate:

• Strong organizational skills

• Strong attention to detail

• Good judgment

• Able to work harmoniously and effectively with others

• Able to preserve confidentiality and exercise discretion

• Able to work under pressure

• Able to manage multiple projects with competing deadlines and priorities

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