AI Enablement Engineer

DRW
Montreal, Canada

Who this role is best for

A natural match if you have experience supporting enterprise AI tools and navigating complex model cost dynamics.

Best fit for

  • Candidates with experience in AI tool support and model optimization in financial services
    — “AI tools drive immense value across the firm”
  • Professionals who can bridge technical and business user needs with a consultative approach
    — “Actively consult with high-spending teams to safely 'downshift' their workloads”
  • Individuals with a track record of evangelizing responsible AI usage and training others
    — “Promote and evangelize effective, responsible use of enterprise AI tools”

Things to consider

  • Commitment to managing cost constraints while ensuring high user adoption and satisfaction
    — “strictly managing an exponentially growing cost curve”
  • Geographic flexibility may be required due to the firm's global presence
    — “Headquartered in Chicago with offices throughout the U.S., Canada, Europe, and Asia”

How to stand out

  • Highlight experience with enterprise AI tools and cost optimization strategies in your resume
    — “providing low-friction access to the best frontier AI tools while strictly managing an exponentially growing cost curve”
  • Demonstrate your understanding of prompt engineering and model behaviors in your interview responses
    — “Technical fluency in prompt engineering and a deep, practical understanding of current LLM capabilities, behaviors, and limitations”
  • Showcase your ability to identify and communicate user pain points to engineering teams
    — “Identify weaknesses in tooling, prompt engineering, or model routing, and feed user pain points directly to the AI Platform Engineering focus area”
Pace · SteadyCollaboration · HighAutonomy · MediumDecision Impact · Team

Derived from job-description analysis by Serendipath's career intelligence engine.

What success looks like

  • Managed support queues for enterprise AI tools
  • Consulted with high-spending teams to optimize AI tool usage
Typical background
Experience in AI and machine learningStrong customer-facing communication skills

Skills & requirements

Required

AI ToolsPrompt EngineeringLLM Capabilities

Preferred

Developer EnvironmentsIdes

Stack & domain

AI ToolsLLM CapabilitiesPrompt EngineeringCustomer-facing CommunicationConsulting

About the role

Original posting from DRW via Greenhouse

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.

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California residents, please review the California Privacy Notice for information about certain legal rights at https://drw.com/california-privacy-notice.

#LI-VD1 

Source: DRW careers (Greenhouse)

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