3h ago
New
$175,000 to $225,000/yr

AI Enablement Engineer

United StatesUnited States·Chicagomid
Customer SupportIt Support Specialist
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Quick Summary

Key Responsibilities

Own the support queue for enterprise generative AI tools. Troubleshoot IDE integrations (Cursor, Devin), chat interfaces, and access issues.

Requirements Summary

Strong customer-facing communication skills and a "white-glove" support mentality. Technical fluency in prompt engineering and a deep, practical understanding of current LLM capabilities, behaviors,

Technical Tools
Customer SupportIt Support Specialist

As AI tools drive immense value across the firm, our organization faces a "Dual Mandate": providing low-friction access to the best frontier AI tools while strictly managing an exponentially growing cost curve. The newly formed AI Platform Team owns this unified mission. While the engineering side of our team builds the platform rails, the AI Platform Support & Enablement focus area acts as the crucial "human-in-the-loop." We are dedicated to ensuring high user velocity and frictionless adoption of AI tools while actively managing firm-wide cost efficiency and user education. 

We are seeking AI Enablement Engineers to own the data plane user experience. You will be the face of AI tooling for the firm, supporting developers and business users who use tools such as Cursor, Devin, ChatGPT, and LibreChat. 

Responsibilities

~1 min read
  • →Own the support queue for enterprise generative AI tools. Troubleshoot IDE integrations (Cursor, Devin), chat interfaces, and access issues. 
  • →Actively consult with high-spending teams to safely "downshift" their workloads from expensive proprietary models (like Claude Opus) to cheaper mid-tier or internal open-weight models without degrading output quality. 
  • →Review manual quota-increase requests triggered by the Management Plane and guide users through spend visibility via internal dashboards. 
  • →Identify weaknesses in tooling, prompt engineering, or model routing, and feed user pain points directly to the AI Platform Engineering focus area to inform the technical roadmap. 
  • →Promote and evangelize effective, responsible use of enterprise AI tools, for example, by helping users understand and adopt AI 'golden paths', sharing success stories, and leading workshops.

Requirements

~1 min read
  • Strong customer-facing communication skills and a "white-glove" support mentality. 
  • Technical fluency in prompt engineering and a deep, practical understanding of current LLM capabilities, behaviors, and limitations. 
  • Familiarity with developer environments, IDEs (VS Code, Cursor) and CLI tools (such as Claude or Codex), is a major plus
  • Strong context of internal firm culture, user base, and existing support channels.

The annual base salary range for this position is $175,000 to $225,000 depending on the candidate’s experience, qualifications, and relevant skill set. The position is also eligible for an annual discretionary bonus. In addition, DRW offers a comprehensive suite of employee benefits including group medical, pharmacy, dental and vision insurance, 401k (with discretionary employer match), short and long-term disability, life and AD&D insurance, health savings accounts, and flexible spending accounts.

Location & Eligibility

Where is the job
Chicago, United States
On-site at the office
Who can apply
US

About this job

Pay per year
$175,000–$225,000 a year
152% above the $79,380 median for It Support Specialist jobs on Jobera (466 salaries).
Who can apply
United States
Posted
Today
Employer
has 171 open jobs on Jobera in 7 countries.

Listing Details

Posted
November 3, 2026
First seen
November 3, 2026
Last seen
November 3, 2026

Posting Health

Days active
0
Repost count
0
Trust Level
79%
Scored at
November 3, 2026

Signal breakdown

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AI Enablement Engineer$175,000 to $225,000