by Adrienne Teeley
January 7, 2020

In the early 1990s, the Chicago Mercantile Exchange was a bustling, intense arena to work in.

Don Wilson was in the midst of the chaos, trading Eurodollar options on the floor. The precocious 20-year-old had only recently graduated college and yet was receiving quite an education from the high-octane environment of the Merc. The thrill of the pit is enough to satisfy many people, but for Wilson, it was just the beginning of his fascination with trading. 

After work each day, he went directly home to his studio apartment, where he’d use his enormous beige computer to chart volatility pricing, build risk software and create option-pricing models. The next day, he’d take his findings to the floor and test them. The results were encouraging. 

His focus on the relationship between technology, mathematics and trading made him stand out from his peers. So in 1992, he sized up the risks and made the decision to start his own principal trading firm, DRW. Using all he’d learned from the trading floor and from his side-projects, his firm was built to place a heavy emphasis on technology. 

Today, DRW doesn’t exist solely as a trading firm — it remains focused on identifying and capturing opportunities, which has led to expansion into real estate through Convexity Properties, venture capital by means of DRW Venture Capital, and cryptoassets through Cumberland.

Like Wilson in his early days of trading, employees progress their careers and carve out their place in the industry by living some core tenants of trading: being nimble, keeping an entrepreneurial mindset, taking risks, and staying at the forefront of new technologies. 


CFO, Convexity Properties

Kristen manages Convexity Properties’ portfolio. She’s responsible for handling tasks like securing funding sources, financial planning, overseeing financial reporting and more.

What she’s working on now: “I recently began a major initiative to transition all Convexity reporting, which historically had been handled by DRW’s trading accountants, to my team. We now employ a real estate-specific accounting system to deliver to our users a complete and reliable reporting package each month.” 


Senior Systems Engineer

Jason and his team ensure the day-to-day tech operations at DRW flow seamlessly. There’s a wide variety of teams and industries DRW is involved with, so juggling the varied tech needs of the company is no small feat. 

Why DRW is a good fit: “I’ve progressed my career by providing proactive solutions and process improvements on my team. DRW does a great job of allowing individuals to focus on ideas or projects that they are interested in.” 


drw chicago


What does “staying nimble” mean at your company? In what ways do you personally stay flexible in your role?

Kristen: While Convexity, and real estate in general, clearly do not move as fast as the trading world, we have been able to apply those same principles to an industry that has otherwise operated in a more archaic environment. Our agility allows us to underwrite deals and make offers faster than our competition, and that has certainly provided a leg up that’s similar to how the trading business leverages its innovative personnel and technology. 

Jason: One of the more enjoyable aspects of my job is having exposure to every team at DRW. Given that every team has a unique use case with their own workstations, cell phones, laptops, trading tablets, conference rooms and more, we have to engineer solutions for every single employee, learn from changes and make sure all of our approaches are scalable for the needs of the business. 


Tell us about how DRW takes an entrepreneurial approach to business. How does that impact you at the individual level?

Kristen: At Convexity, we have had the opportunity to build this portfolio from the ground up. DRW as a whole is very entrepreneurial in spirit, and Convexity has allowed me more autonomy to assemble processes and procedures and to test those out as the team evolves. Consistent core elements running deep through all DRW businesses are trust and confidence in its employees — a rarity in today’s world.



DRW team working together


Why is it important to stay ahead of the curve in your industry?

Jason: Technology is at a state of constant change, with new security policies, hardware, operating systems and vulnerabilities, so it is important to keep up on the pulse of tech news to ensure we stay knowledgeable and relevant on the solutions we provide. Coming from a technology background, it was eye-opening to learn that DRW invests so heavily in technology. 


DRW team working together


Risk is a huge component in your industry. How does it factor into your day-to-day work? 

Jason: For a company in the business of managing risk, it’s critical to be at the top of our game to assist with any and all inquiries and problems that employees may encounter. And when there isn’t a fire to put out, a big project for our team is modernizing and enhancing a company-wide intranet.

Kristen: I encounter risk opportunities on a daily basis. Some are a welcome challenge, for instance: Do we push hard on a lender to secure better terms, or risk losing the deal? Others are on a larger scale, like analyzing a property as a hold-sell while putting substantial weight into subjective inputs, hoping the market moves in tandem to those assumptions. 

While a significant portion of my role is self-directed and autonomous, Convexity has a team that, though lean, is particularly talented in their fields of expertise and is available at a moment’s notice when needed. Having those resources at our immediate disposal allows us to remain nimble but also calculated, which provides a certain level of comfort when taking that first step off the ledge.

Jobs at DRW

Chicago Startup GuidesSEE ALL

Best Companies to Work for in Chicago
Coolest Offices in Chicago Tech
Best Perks at Chicago Tech Companies
Women in Chicago Tech
Best Data Science Jobs in Chicago
Best Software Engineer Jobs in Chicago
Best Marketing Jobs in Chicago
Best Design Jobs in Chicago
Best Sales Jobs in Chicago
Your Guide to Healthtech in Chicago
Best Sales Manager Jobs in Chicago
Best Creative Jobs in Chicago