AI Enablement Services Lead
About The Position
Transforming the insurance industry is ambitious, we know. That’s why at Applied, we’re building a team that shows up every day ready to learn, willing to try new things, and driven to deliver innovative software and services that make us indispensable to our customers – all within a culture built on values that make us indispensable to each other too. With 40+ years of experience in the Insurtech game, we’re not just redefining what’s achievable; we’re creating a place where amazing career moments are made possible. Position Overview 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. To keep us headed in the right direction, we’re looking for people who understand winning is a team sport, who value and seek to learn from our team’s diverse experiences and backgrounds, who welcome a challenge and take risks in the pursuit of creating better outcomes for our customers, and who can, at any given time, step back to laugh and have some fun.
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.
Nice To Haves
- 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.
Benefits
- A culture that values who you are and recognizes that you aren’t just an employee; you are a teammate, and you matter. We thrive on the benefits of our different experiences and celebrate the uniqueness our teammates bring to work with them every day.
- We flex our time together , collaborating remotely and in-person to empower our teams to work in the ways that work best for them.
- A comprehensive benefits and compensation package that centers our teammates and helps them to bring their best to work every day:
- Medical, Dental, and Vision Coverage
- Holiday and Vacation Time
- Health & Wellness Days
- A Bonus Day for Your Birthday
Stand Out From the Crowd
Upload your resume and get instant feedback on how well it matches this job.
What This Job Offers
Job Type
Full-time
Career Level
Mid Level
Education Level
No Education Listed
Number of Employees
501-1,000 employees
