Project Manager, AI – Roots

Roots combines machine intelligence and human ingenuity in the form of advanced AI that reads, reasons and infers like humans. Roots’ AI is trained on millions of non-public insurance documents, workflows and systems and continuously learns through interactions with human teams.

This is a chance to step into a product defining role at Roots, creating groundbreaking solutions with agentic capabilities that redefine the modern workplace. You’ll have access to cutting-edge tools and the opportunity to shape the future of AI-driven systems, making a lasting impact on Roots’ core products and beyond.

Roots is seeking an execution-focused Project Manager, AI to join our Customer Success team and lead the end-to-end delivery of AI-powered automations for some of the world’s most complex insurance carriers.

We’re building cutting-edge infrastructure that powers real-time document processing, custom model deployment, and multimodal intelligence. Our platform automates complex insurance workflows with 98%+ accuracy and speed, helping carriers and brokers go from months to value in just weeks. Your role is to drive the execution that brings these AI technologies into production, translating technical performance into measurable ROI.

You will join the Customer Success team, where we bridge the gap between AI innovation and P&C insurance operations. Reporting to a Customer Success Manager, you will fully own the execution of 2–3 concurrent implementation projects.

For every project, you will lead a dedicated cross-functional team (1 Business Analyst, 1 Solution Architect, and 1 Automation Engineer) to automate workflows like claims indexing and underwriting. Your success is measured by more than just “go-live”, as you will own the reporting of automation metrics & ROI, proving exactly how our AI-driven results outperform legacy manual processes.

• Drive the end-to-end delivery of 2-3 concurrent AI implementations, moving projects from initial kickoff to full production while managing timelines, technical risks, and resource dependencies.

• Own the customer-facing implementation journey, leading all stakeholder communication and expectation setting while reporting on key performance metrics (e.g., STP and accuracy) to demonstrate clear value over legacy manual processes.

• Orchestrate the day-to-day execution of a cross-functional squad (Business Analyst, Solution Architect, and Automation Engineer), ensuring technical builds and model tuning remain strictly aligned with customer business objectives.

• Maintain rigorous project governance and documentation, including requirements, timelines, and the tracking of automation performance milestones to ensure a seamless transition from UAT to production.

• 2–3 years of experience as a Project Manager, Implementation Manager, or similar role leading technical software implementations, with a proven track record of owning projects from kickoff to production.

• Process Engineering: Experience mapping complex business workflows and translating them into clear technical requirements for BAs and Engineers.

• Data Literacy: Comfortable interpreting automation performance data (STP, accuracy) and translating technical results into business-focused progress reports.

• Conflict & Change Management: Demonstrated ability to navigate customer friction, manage scope creep, and confidently “push back” on stakeholders to protect delivery timelines.

• Domain Aptitude: Familiarity with the P&C insurance lifecycle (Claims or Underwriting) or a high capacity to master complex, document-heavy industries quickly.

• Highly organized, resilient, and confident communicator who knows when to push back, escalate, or say no when necessary.

Apply here.