---
title: 'Team Lead, AI Engineering at DRW'
canonical: 'https://feeny.ai/job/team-lead-ai-engineering-drw-chicago-6w0ee243y8f4'
type: 'job'
last_seen: '2026-09-13'
---

# Team Lead, AI Engineering at DRW 

- **Company:** DRW 
- **Location:** Chicago, IL
- **Posted:** 2026-09-09
- **Last confirmed live:** 2026-09-13
- **Apply:** https://job-boards.greenhouse.io/drweng/jobs/8186768

## 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 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.

Required 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.

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.

For more information about DRW's processing activities and our use of job applicants' data, please view our Privacy Notice at https://drw.com/privacy-notice.

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

## #LI-VD1

## About DRW 

## Company Overview
- **One-liner**: DRW is a diversified principal trading firm that leverages technology, research, and risk management to capture trading and investment opportunities globally across traditional and cryptoasset markets.
- **Entity Type**: Private (Privately Held)
- **Headquarters**: Chicago, Illinois, United States
- **Founded**: Year not publicly specified on the website, but linked data suggests operations since at least the early 2000s (acquired Chopper Trading in 2015).
- **Founders**: Founders are not publicly named on the company website or in standard public profiles.

## Core Business
- **Primary industry/industries**: Financial Services, Proprietary Trading, Cryptoassets, Real Estate, Venture Capital
- **Target customers**: Institutional counterparties (for Cumberland, its crypto subsidiary); the firm trades its own capital across global markets (B2B/institutional focus).
- **Mission or purpose statement**: The company describes itself as a team of "innovative and ambitious individuals who use the power of free markets to solve challenging problems, capture opportunities, and pursue positive change." [drw.com](https://www.drw.com/work-at-drw)

## Products & Services
- **Proprietary Trading**: DRW trades a wide range of asset classes including fixed income, ETFs, equities, FX, commodities, and cryptoassets, using sophisticated technologies to provide liquidity and capture opportunities.
- **Cumberland**: A subsidiary that provides deep liquidity in cryptoassets to large institutional counterparties and explores DeFi solutions. [drw.com](https://drw.com/our-subsidiaries)
- **DRW Venture Capital**: A VC practice that takes a disciplined approach to investing in financial and enterprise technology companies. [drw.com](https://drw.com/our-subsidiaries)
- **DRW Real Estate**: A fully integrated real estate investment arm that invests in bespoke projects. [drw.com](https://drw.com/our-subsidiaries)
- **NX**: A team that designs, builds, and operates a sophisticated global network for the firm. [drw.com](https://drw.com/our-subsidiaries)
- **Artemeter**: A subsidiary providing full-service carbon financing solutions to help clients achieve decarbonization goals. [drw.com](https://drw.com/our-subsidiaries)

## Market Standing
- **Valuation/Market Cap**: Not publicly disclosed (private company).
- **Key Metric**: Annual Revenue estimated at **$485.0M** (per LinkedIn data). [linkedin.com](https://www.linkedin.com/company/drw)
- **Notable Investors/Partners**: Not applicable (privately held and self-funded). Notable subsidiaries include Cumberland (crypto).
- **Growth Signals**: Headcount growth of **+10.6% YoY** (adding 233 people), reaching 1,628 employees. Active job postings increased **+53.8% YoY**. [linkedin.com](https://www.linkedin.com/company/drw)

## Competitive Advantages
- **Diversified Approach**: Unlike many trading firms that focus on a single asset class, DRW trades across many asset classes and instruments, with horizons from seconds to years. [drw.com](https://www.drw.com/work-at-drw)
- **Technology & Research**: Heavy investment in sophisticated technology, research, and risk management to find and capture opportunities globally.
- **Low Ego, Little Hierarchy**: The company explicitly states a culture of "low ego, little hierarchy and a commitment to continuous learning." [drw.com](https://www.drw.com/work-at-drw)
- **Stability & Startup Spirit**: Described as offering "the best of both worlds: the opportunity and spirit of a startup and the benefits and stability of an established, experienced firm." [drw.com](https://www.drw.com/work-at-drw)

## Strategic Focus
- **Expansion into Non-Traditional Strategies**: The firm has expanded beyond traditional trading into real estate, venture capital, and cryptoassets, indicating a focus on long-term, strategic, and diversified growth. [drw.com](https://drw.com/our-subsidiaries)
- **Continuous Innovation**: Focus on solving challenging problems, discussing technical and research topics, and challenging consensus to achieve high standards. [drw.com](https://www.drw.com/work-at-drw)
- **Global Reach**: Operates in 29 countries with offices in the US, UK, Canada, Singapore, Netherlands, and Israel, signaling a commitment to global market participation. [linkedin.com](https://www.linkedin.com/company/drw)

## Why Work Here
- **Culture & Philosophy**: The company emphasizes "low ego, little hierarchy," "challenge consensus," "integrity," and "continuous learning." It seeks curious problem solvers with quantitative mindsets. [drw.com](https://www.drw.com/work-at-drw)
- **Compensation & Benefits**: Rated 4.3/5.0 on compensation. [linkedin.com](https://www.linkedin.com/company/drw) Perks include daily catered breakfast & lunch, monthly tastings, massages, yoga classes, meditation, gym subsidy, game room, and social events. [drw.com](https://www.drw.com/work-at-drw)
- **Work Environment**: Offers flexible work arrangements. The culture is described as fast-paced, collaborative, and intellectually rigorous. [drw.com](https://www.drw.com/work-at-drw)
- **Engineering Culture**: A significant portion of the workforce is technical (615 employees, 25% of total). Roles include Quantitative AI Strategist, Python Software Engineer, Data Developer, HPC Specialist, and Trading Systems Engineer. [linkedin.com](https://www.linkedin.com/company/drw)
- **Global Offices**: Hybrid/office presence in Chicago (HQ), New York, London, Amsterdam, Singapore, Montreal, Tel Aviv, and more. [drw.com](https://www.drw.com/work-at-drw/listings)

## Sources
1. [drw.com - Work at DRW](https://www.drw.com/work-at-drw)
2. [drw.com - Our Subsidiaries](https://drw.com/our-subsidiaries)
3. [linkedin.com - DRW Company Profile](https://www.linkedin.com/company/drw)
4. [greenhouse.io - DRW Engineering Jobs](http://job-boards.greenhouse.io/drweng)

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