AI Enablement Services Lead

Job Description
Amazing Career Moments Happen Here
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.
What You'll Do

• 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.

We're Excited to Learn More About You
Your experience may include:

• 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.

We know that talent comes from all backgrounds and experience levels. We encourage military members and their spouses as well as candidates without a degree or a background in tech to apply!
When You Join Team Applied, You Can Expect:
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

Learn more about the people behind our products at https://www1.appliedsystems.com/en-us/about-us/jobs/
Our targeted starting base salary in the United States for this position ranges from $140,000 - $180,000 USD. To determine a new team member's starting pay, we consider a variety of factors, including someone's depth, breadth, and variety of experience, skills, and responsibilities. Depending on the role, team members may also be eligible to participate in additional compensation plans such as bonus and commission.
Your Security Matters:
Our candidates' personal information and online safety are top of mind for us. At Applied, we proactively protect your personal information and only communicate with candidates via a secure @appliedsystems.com email or through our official careers portal. Recruiters will never request payments, ask for financial account information or sensitive information like social security numbers.
AI Utilization
We leverage AI tools to streamline parts of our recruitment workflow (such as resume parsing and interview scheduling). However, candidate screening, interviews, and final decisions are conducted by real humans.
EEO Statement
Applied Systems is proud to be an Equal Employment Opportunity Employer. Diversity and Inclusion is a business imperative and is a part of building our brand and reputation. At Applied, we don't discriminate, and we are committed to recruit, develop, retain, and promote regardless of race, religion, color, national origin, sexual orientation, gender identity, disability, age, veteran status, and other protected status as required by applicable law.
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