Executive Chatbot Development Jobs in Chicago, IL

Apply now: Senior Project Manager, location is Northbrook, IL. The start date is July 13th for this 6-month contract position with potential extension into 2027.

Job Title: Senior Project/Program ManagerLocation-Type: Hybrid (3 days a week onsite in Northbrook, IL)Start Date Is: July 13th, 2026Duration: 6-Month Contract (through EOY, potential extension into 2027)Compensation Range: $75-$95/hrBenefits: Eligible for Health, Dental, Vision, 401KMust be authorized to work in the U.S. This position is not eligible for sponsorship.

Job Description:

• The client is seeking a Senior Program Manager to lead the implementation of an AI-powered customer service chatbot initiative. This highly visible business transformation project will introduce a new communication channel and requires a strong leader who can drive roadmap development, stakeholder alignment, organizational change management, vendor coordination, and successful user adoption.

Day-to-Day Responsibilities:

• Lead end-to-end delivery of an AI-powered customer service chatbot implementation
• Drive roadmap planning, project execution, timeline management, and stakeholder communication
• Partner with business leaders, customer service teams, technical teams, vendors, and executive stakeholders
• Support organizational change management efforts and drive user adoption of the new communication channel
• Collaborate with internal developers, Solution Architects, and Business Analysts throughout the project lifecycle
• Ensure AI models are trained with quality data and aligned to business objectives
• Monitor implementation progress and ensure successful delivery of project milestones
• Create executive-level presentations and project updates using PowerPoint
• Manage project plans, risks, dependencies, and resource coordination
• Facilitate Agile ceremonies as needed (approximately 5-10% Scrum Master responsibilities)
• Utilize Jira and project management tools to track work and maintain project visibility
• Coordinate with customer service teams to ensure the solution delivers an exceptional customer experience
• Support implementation and go-live activities

Minimum Requirements:

• 8 years of Project Management experience leading enterprise technology initiatives
• Prior experience leading a customer service AI chatbot implementation from inception through deployment
• Experience managing 0-to-1 transformational projects involving new customer communication channels
• Strong stakeholder management and executive communication skills
• Experience building project roadmaps and driving organizational adoption of new technologies
• Experience working with third-party software vendors and implementation partners
• Strong knowledge of Agile methodologies and Scrum practices
• Hands-on experience with Jira and project management tools
• Experience working within regulated environments requiring HIPAA, compliance, privacy, or regulatory considerations
• Strong organizational change management experience
• Ability to adapt quickly, think on your feet, and navigate evolving project requirements
• Excellent communication, presentation, and interpersonal skills

Preferred Qualifications:

• Experience implementing AI-powered customer service, conversational AI, or chatbot solutions
• Experience integrating customer-facing technologies with eCommerce or customer service platforms
• Scrum Master certification or experience supporting Agile delivery teams