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This position has closed. DRW removed this listing from their careers page on Oct 6, 2026. The interview prep below is still useful, and there are similar open roles at the bottom of this page.

Team Lead, AI Engineering

DRW · Chicago, IL · $200,000–$250,000 a year · IO - Development & Operations

Posted Sep 9, 2026 · We last checked this listing on Oct 5, 2026

Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

The team is new. How would you hire and shape it in your first six months?

What they are checking: Whether they can build a team with the right mix of engineers and support people from scratch.

Tell me about a time you led engineers through a fast-changing technical area.

What they are checking: Whether they can keep a team focused while the tools and vendors shift every few months.

What would you do

The AI Platform Team has a dual mandate: easy access to the best frontier AI tools and control over a fast-growing cost curve. How would you balance those two?

What they are checking: Whether they can serve users well while building real cost controls, instead of favoring one side.

The role includes human-in-the-loop support to guide users. How would you run that so it scales?

What they are checking: Whether they turn support work into guides, defaults and tooling rather than an endless queue.

A heavy user's monthly AI spend has tripled. How do you approach the conversation?

What they are checking: Whether they investigate value and offer cheaper paths before simply cutting someone off.

What would you do if a new frontier model launched and every desk wanted it immediately?

What they are checking: Their process for quick vetting and controlled rollout without blocking eager users for weeks.

About the work

How would you design a central layer that routes users to the most cost-effective model for their task?

What they are checking: Thinking about routing rules, evaluation, fallbacks and usage tracking that make cost-aware routing work.

What governance would you put around AI tool use in a trading firm?

What they are checking: Awareness of data protection, logging, access control and acceptable use in a regulated, confidential setting.

How would you measure whether AI tools are actually creating value across the firm?

What they are checking: Ability to pick useful adoption and outcome measures instead of only counting tokens or seats.

How do you evaluate whether a cheaper model is good enough to replace a frontier model for a use case?

What they are checking: Use of task-specific evaluations and real samples rather than general benchmark scores.

Practice this interview out loud.

Offer builds a real interview for this exact role at DRW from your resume and this job description, asks the questions one at a time, and tells you what landed. The first one is free.

Practice this out loud

The full job description

As published by DRW.

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: &nbsp; 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&nbsp; AI Platform Team &nbsp;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. &nbsp; The Role: &nbsp; 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. &nbsp; Key Responsibilities: &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="3" data-list-defn-props="{"335551671":0,"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="0" data-aria-level="1"> Manage a dual-focus team consisting of software engineers and AI support specialists, balancing rigorous agile engineering delivery with high-touch user enablement. &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="3" data-list-defn-props="{"335551671":0,"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="1" data-aria-level="1"> Oversee the technical vision for our "Federated Management Plane," managing the development of multi-engine API gateways, asynchronous data pipelines, and progressive friction policies. &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="3" data-list-defn-props="{"335551671":0,"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="2" data-aria-level="1"> Translate insights gathered from the Support queue (e.g., prompt engineering struggles, quota requests) directly into technical requirements for the Engineering&nbsp;focus area&nbsp;to automate. &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="3" data-list-defn-props="{"335551671":0,"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="3" data-aria-level="1"> Act as the primary DRI connecting our Cloud foundation, 3rd-party SaaS vendors, and our internal&nbsp;on-premise&nbsp;AI hardware to ensure seamless model routing. &nbsp; Required Qualifications: &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="3" data-list-defn-props="{"335551671":0,"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="4" data-aria-level="1"> Proven experience managing cross-functional technical teams, ideally spanning software engineering, platform operations, or product support. &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="3" data-list-defn-props="{"335551671":0,"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="5" data-aria-level="1"> Strong architectural background with technical&nbsp;expertise&nbsp;in distributed systems, API gateway management, and Go/Python. &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="3" data-list-defn-props="{"335551671":0,"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="6" data-aria-level="1"> Strategic mindset with the ability to define operational governance, cost-control workflows, and vendor management strategies. &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="3" data-list-defn-props="{"335551671":0,"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="7" data-aria-level="1"> Ability to navigate ambiguity and transition rapid prototypes into stable, permanent enterprise platforms. &nbsp; &nbsp; 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 &nbsp;