Skip to content

Posted November 3, 2026

AI Enablement Engineer

DRW

Category:Trading Operations

Location:ChicagoNew York

Seniority
Medior
Employment type
Full-time
Salary (per year)
$175k–$225k
Bonus
Yes

Requirements

  • 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.
  • Strong context of internal firm culture, user base, and existing support channels.

Nice to have

  • Familiarity with developer environments, IDEs (VS Code, Cursor) and CLI tools (such as Claude or Codex), is a major plus

About the role

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

  • 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.

What you'll get

  • $175k–$225k base salary
  • 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
  • flexible spending accounts

Skills

prompt engineering · LLM capabilities · IDE integrations · Cursor · Devin · ChatGPT · LibreChat · VS Code · CLI tools · Claude · Codex