AI Enablement Engineer

DRW Holdings, LLC.; Chicago (IL); On-site; USD 175,000 - 225,000; Full time

Benefits offered by this job

Medical insurance

Dental insurance

Vision insurance

401(k) with discretionary match

Short & long-term disability

Life and AD&D insurance

Health Savings Account

Flexible Spending Accounts

Job summary

DRW Holdings, LLC in Chicago seeks an AI Enablement Engineer to own the data plane user experience for enterprise AI tools such as Cursor, Devin, ChatGPT and LibreChat. You will be the face of AI tooling for developers and business users.

You will troubleshoot tool integrations, help teams downshift to cost-effective models, review quota requests, and feed user feedback into the roadmap. Competitive salary and robust benefits offered.

Qualifications

• Excellent written and verbal communication with a white-glove support mindset.
• Strong understanding of current LLM capabilities and limitations.
• Experience with developer environments and AI tooling is a plus.
• Knowledge of enterprise AI tool usage and governance.

Responsibilities

• Own the support queue for enterprise generative AI tools and troubleshoot integrations.
• Consult with high-spending teams to downshift workloads to cheaper models without quality loss.
• Review quota-increase requests and guide spend visibility via internal dashboards.
• Identify tooling weaknesses and relay pain points to the AI Platform Engineering team.
• Promote responsible use and run workshops on AI golden paths.

Skills

Customer-facing communication

Prompt engineering knowledge

LLM capabilities awareness

Developer tool familiarity

Tools

VS Code

Cursor

Claude

Codex

Job description

DRW is a diversified trading firm with over 3 decades of experience bringing sophisticated technology and exceptional people together to operate in markets around the world. We value autonomy and the ability to quickly pivot to capture opportunities, so we operate using our own capital and trading at our own risk.

Headquartered in Chicago with offices throughout the U.S., Canada, Europe, and Asia, we trade a variety of asset classes including Fixed Income, ETFs, Equities, FX, Commodities and Energy across all major global markets. We have also leveraged our expertise and technology to expand into three non-traditional strategies: real estate, venture capital and cryptoassets.

We operate with respect, curiosity and open minds. The people who thrive here share our belief that it’s not just what we do that matters it's how we do it. DRW is a place of high expectations, integrity, innovation and a willingness to challenge consensus.

The Team:

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.

The Role:

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.

Key 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.

Required Qualifications:

• 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.

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