Team Lead, AI Engineering

DRW•Chicago, IL

About The Position

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 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. 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. 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.

Requirements

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 gathered from the Support queue (e.g., prompt engineering struggles, quota requests) directly 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.