---
title: 'Systems Engineer - Microsoft at DRW'
canonical: 'https://feeny.ai/job/systems-engineer-microsoft-drw-chicago-y67bnrc078vf'
type: 'job'
last_seen: '2026-09-13'
---

# Systems Engineer - Microsoft at DRW 

- **Company:** DRW 
- **Location:** Chicago, IL
- **Posted:** 2026-09-11
- **Last confirmed live:** 2026-09-13
- **Apply:** https://job-boards.greenhouse.io/drweng/jobs/8180036

## 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.

Our philosophy:

- We believe in relentless automation of repetitive tasks.
- We have the curiosity and drive to dig deep and find creative solutions.
- We believe our goal is to find the right solution rather than always being right.
- We provide exceptional customer service to our teams and trading desks.
- We care more that the right thing is done than about rigid job descriptions or boundaries.

What you’ll do:

- Administer core Microsoft services: Active Directory, DNS, DHCP, Group Policy, Exchange (on-premise, Online, hybrid).
- Deploy, maintain and support Windows Server environments (2016–2025).
- Support Microsoft cloud services (Entra ID, OneDrive, Copilot, Microsoft 365 services).
- Configure single sign on and federation (SAML, OAuth/OIDC, SCIM).
- Triage and resolve tickets from the operations queue; respond to critical production incidents.
- Implement planned and ad hoc changes in accordance with firmwide change management processes.
- Maintain clear system documentation and capture specialized configurations as repeatable runbooks.
- Participate in a global support team with on call rotation and occasional weekend maintenance.

Your background:

- Experience managing Windows Server infrastructure in high visibility, mission critical environments.
- Experience administering Windows Server services: Active Directory, Group Policy, DNS, DHCP, Failover Clustering.
- Experience with Entra ID, Exchange (Server/Online/Hybrid) and MECM (SCCM) is preferred.
- You can use scripts (e.g. PowerShell, Python) to automate routine administrative tasks.
- Knowledge of networking fundamentals, server hardware and VM deployments.
- Strong written and verbal communication skills. You can work across teams and have evidence-based discussions on technical and operational topics.
- You are eager to learn, collaborate, and find solutions under interesting constraints.

Bonus points if you have:

- Experience with Splunk, Grafana, Alertmanager, Prometheus.
- Familiarity with DevOps/CI CD and IaC practices, containerization and Kubernetes.
- Prior experience in the trading or financial services industry.

The annual base salary range for this position is $120,000 to $160,000 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-SK1]

## 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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