Role: Senior Project Manager – Conversational AI / Chatbots

Location: Boston, MA

Experience: 10+ Years

Job Type: Contract

Job Summary

We are seeking an experienced Senior Project Manager to lead the delivery of enterprise Conversational AI and Chatbot initiatives. The ideal candidate will have strong experience managing Agile technology programs involving AI, chatbot platforms, digital transformation, platform integrations, and cross-functional teams. This role requires expertise in project governance, sprint planning, stakeholder management, release management, UAT coordination, and post-production hypercare.

Key Responsibilities

• Lead end-to-end delivery of Conversational AI and Chatbot implementation projects.
• Manage Agile project governance, sprint planning, release planning, and delivery milestones.
• Coordinate with Product Owners, Scrum Masters, Business Analysts, Architects, Developers, QA, Vendors, and Business SMEs.
• Facilitate backlog grooming, sprint planning, sprint reviews, retrospectives, and show-and-tell sessions.
• Manage project scope, timelines, resource planning, risks, dependencies, and issue resolution.
• Track project deliverables using RAID logs, dependency trackers, decision logs, and status reports.
• Coordinate UAT planning, defect management, release readiness, production deployment, and hypercare activities.
• Manage vendor coordination and third-party integrations including APIs, AI platforms, mobile applications, and backend systems.
• Ensure governance documentation, project reporting, and executive communication are maintained throughout the project lifecycle.
• Drive stakeholder communication and escalation management across business and technology teams.

Required Skills

• 10+ years of Project Management experience.
• Strong experience managing Agile software development and enterprise technology projects.
• Experience delivering Conversational AI, Chatbot, AI/ML, Automation, or Digital Transformation projects.
• Hands-on experience with Scrum ceremonies, sprint planning, backlog management, and release management.
• Experience coordinating UAT, production deployments, and hypercare support.
• Strong experience managing cross-functional teams, vendors, and executive stakeholders.
• Experience with APIs, system integrations, environment readiness, and third-party dependencies.
• Excellent communication, leadership, risk management, and stakeholder management skills.

Preferred Skills

• Healthcare or Health Insurance industry experience.
• Experience with Conversational AI platforms, LLMs, GenAI, or AI automation.
• Experience with Jira, Confluence, Azure DevOps, MS Project, or similar project management tools.
• PMP, PMI-ACP, CSM, or SAFe certification preferred.