AI Enablement Engineer

DRW•Chicago, NY

About The Position

DRW is seeking AI Enablement Engineers for its newly formed AI Platform Team. The team has a dual mandate: provide low-friction access to frontier AI tools while managing the rapidly growing cost curve. The AI Platform Support & Enablement focus area helps users adopt AI tools efficiently while supporting firm-wide cost management and user education. The AI Enablement Engineer owns the data-plane user experience and serves as the firm's user-facing contact for AI tools, supporting developers and business users of products such as Cursor, Devin, ChatGPT, and LibreChat. The role combines enterprise tool support, cost-conscious usage guidance, spend visibility, user education, and feedback to the AI Platform Engineering team.

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 Haves

  • Familiarity with developer environments, IDEs such as VS Code and Cursor, and CLI tools such as Claude or Codex.

Responsibilities

  • Own the support queue for enterprise generative AI tools.
  • Troubleshoot IDE integrations, chat interfaces, and access issues, including tools such as Cursor and Devin.
  • Consult with high-spending teams to help shift workloads from expensive proprietary models to lower-cost 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 using internal dashboards.
  • Identify weaknesses in tooling, prompt engineering, or model routing, and share user pain points with the AI Platform Engineering focus area to inform its technical roadmap.
  • Promote effective and responsible use of enterprise AI tools by helping users adopt AI golden paths, sharing success stories, and leading workshops.

Benefits

  • Annual discretionary bonus eligibility.
  • Group medical insurance.
  • Pharmacy insurance.
  • Dental insurance.
  • Vision insurance.
  • 401(k) with discretionary employer match.
  • Short- and long-term disability insurance.
  • Life and AD&D insurance.
  • Health savings accounts.
  • Flexible spending accounts.
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