AI Enablement Services Lead

Applied Systems, Inc.•Chicago, IL

3d•$140,000 - $180,000•Hybrid

About The Position

We’re searching for a AI Enablement Services Lead to join our Professional Services team (Implementation, PMO, Data, Customer Success) in a hybrid location from our Chicago office. As the AI Enablement Services Lead, you will be the architect of the "Next-Gen Professional Services" organization. You are responsible for identifying, building, and deploying AI-driven capabilities—including agentic workflows and automated enablement tools—that empower our delivery teams. Your goal is to transform how we implement software and manage customer success by injecting AI into the "connective tissue" of our operations to drastically improve speed, quality, and capacity.

Requirements

The "Hybrid" Mindset: A rare blend of Professional Services operational excellence and a deep understanding of AI/LLM capabilities.
Technical Fluency: Familiarity with the AI landscape (Prompt Engineering, Agentic Frameworks like LangChain/AutoGPT, and RAG architectures). You don't need to be a developer, but you must speak "Engineer."
Change Management: Proven ability to lead teams through digital transformation. People are often wary of automation; you need to sell the "augmentation" story.
Process Engineering: Experience in Six Sigma, Lean, or specialized PS frameworks (like TSIA) is a major plus.
Industry Context: Experience in InsurTech or complex SaaS migrations is highly preferred.

Responsibilities

Agentic Strategy & Deployment: Design and oversee the development of "AI Agents" (agentic workers) to handle repetitive tasks within Data Migration, Project Management, and Implementation.
PS Lifecycle Automation: Analyze the end-to-end delivery journey to identify friction points. Build AI solutions to automate documentation, risk identification in project health, and data mapping.
Enablement & Adoption: Create the "AI Playbook" for the Professional Services team. Ensure Implementation Consultants and Customer Success Managers (CSMs) are not just using AI, but are proficient in leveraging it to provide higher-value strategic consulting.
Quality & Speed Optimization: Utilize LLMs and RAG (Retrieval-Augmented Generation) to provide real-time guidance to delivery teams, ensuring a "gold standard" of implementation regardless of the consultant's tenure.
Cross-Functional Collaboration: Partner with Product and Engineering to ensure the internal AI tools for PS align with the broader Applied Systems product roadmap.