Team Lead, AI Engineering

DRW Holdings, LLC.; Chicago (IL); On-site; USD 200,000 - 250,000; Full time

Benefits offered by this job

Employee benefits

Job summary

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

We are building an AI Platform Team and seek an AI Platform Team Lead to oversee both AI Platform Engineering and AI Support & Enablement.

Qualifications

• Proven experience managing cross-functional technical teams, ideally spanning software engineering, platform operations, or product support.
• Strong architectural background with technical expertise in distributed systems, API gateway management, and Go/Python.
• Strategic mindset with the ability to define operational governance, cost-control workflows, and vendor management strategies.
• Ability to navigate ambiguity and transition rapid prototypes into stable, permanent enterprise platforms.

Responsibilities

• Manage a dual-focus team consisting of software engineers and AI support specialists, balancing rigorous agile engineering delivery with high-touch user enablement.
• Oversee the technical vision for our Federated Management Plane, managing the development of multi-engine API gateways, asynchronous data pipelines, and progressive friction policies.
• Translate insights from the Support queue into technical requirements for the Engineering focus area to automate.
• Act as the primary DRI connecting our Cloud foundation, 3rd-party SaaS vendors, and our internal on-premise AI hardware to ensure seamless model routing.

Skills

Cross-functional leadership

Distributed systems

API gateway management

Go/Python

Architectural background

Vendor management

Cost-control workflows

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 managing an exponentially growing cost curve. The AI Platform Team is a net-new, unified group responsible for building both the centralized software/governance layers and providing the human-in-the-loop support required to route users to the most cost-effective models.

The Role:

We are seeking an AI Platform Team Lead to serve as the overarching leader of this newly formed, unified team. You will oversee both focus areas: AI Platform Engineering and AI Support & Enablement. By managing both the technical platform and the user support experience under a single umbrella, you will ensure a frictionless feedback loop in which user pain points, tool limitations, and cost data instantly inform your engineering roadmap and automated governance policies.

Key Responsibilities:

• Manage a dual-focus team consisting of software engineers and AI support specialists, balancing rigorous agile engineering delivery with high-touch user enablement.
• Oversee the technical vision for our "Federated Management Plane," managing the development of multi-engine API gateways, asynchronous data pipelines, and progressive friction policies.
• Translate insights gathered from the Support queue (e.g., prompt engineering struggles, quota requests) directly into technical requirements for the Engineeringfocus areato automate.
• Act as the primary DRI connecting our Cloud foundation, 3rd-party SaaS vendors, and our internalon-premiseAI hardware to ensure seamless model routing.

Required Qualifications:

• Proven experience managing cross-functional technical teams, ideally spanning software engineering, platform operations, or product support.
• Strong architectural background with technicalexpertisein distributed systems, API gateway management, and Go/Python.
• Strategic mindset with the ability to define operational governance, cost-control workflows, and vendor management strategies.
• Ability to navigate ambiguity and transition rapid prototypes into stable, permanent enterprise platforms.

The annual base salary range for this position is $200,000 to $250,000 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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