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Head of Trading

| Chicago

About Us
Topstep is a high-growth, innovative, B2C company challenging the traditional retail trading model in the futures, foreign exchange and equities spaces. Having attracted over 30,000 traders from more than 160 countries since launching in 2012, we are not slowing down anytime soon!

A career at Topstep places you at the intersection of technology, finance, and marketing for one of the fastest growing companies in Chicago. We were named #14 on Crain’s Best Places to Work 2018, and have also earned recognition on the 2017 Inc. 5000 list of the fastest-growing private companies in the U.S. We are growing our passionate team, user base, and business model, all the while reinventing the retail brokerage industry.

The Role
At Topstep, individuals fully own their roles and are charged with meaningfully driving results. We work fast and continuously optimize our products to reach more and more traders worldwide.

The Head of Trading is accountable for the profitability of Topstep’s proprietary retail futures and forex trading business.

The ideal candidate is enthusiastic about working in a fast-paced environment embracing innovation and continuously improving. S/he will have a keen attention to detail and the ability to take ideas from concept to execution. We're looking for a self-starter who learns quickly, loves technology, and has proven problem-solving and people skills.

Are you excited about this opportunity? If so, read on…

What You’ll Do

  • Successfully lead daily operations of Topstep’s proprietary trading business, including but not limited to: oversee capital allocation, facilitate strong cross-departmental communication, and lead the Risk Management Team.
  • Establish and implement a profitable strategy for Topstep, designed to increase the upside potential and reduce the downside risk.
  • Establish and cultivate relationships with partners. 
  • Identify new business opportunities and partnerships to enhance our traders’ experiences.
  • Improve the processes and procedures to provide a great experience throughout the user journey.
  • Manage profit and loss statements.
  • Assist in budget preparation and expense management activities.
  • Review trader performance, costs, operations, withdrawals, and forecast data to establish and determine progress toward meeting stated goals and objectives. 
  • Evaluate and decide upon key investments in equipment and technology for Topstep.
  • Ensure we adhere to evolving legal and compliance changes.
  • Contribute to broader organizational strategic planning.
  • Ensure risk management solutions (automated and manual) work flawlessly 24/7/365.
  • Keep apprised of changing elements of the industry including technology, brokerages, fees, etc.
  • Report on the key drivers of the department to the Executive Team on a recurring basis.
  • Provide direct management and leadership to members of the Topstep team.
  • Forecast future hiring needs and oversee recruiting, onboarding and orientation for new team members.

What You’ll Need

  • Bachelor's degree in Finance, Business or related field.
  • 5+ years of management experience in a team-oriented workplace 
  • Demonstrated ability to lead and develop a department and team members
  • Must be business-minded with strategic thinking abilities
  • Experience as a trader 
  • 5+ years in a risk management or similar role
  • Demonstrated reporting and presentation skills
  • Outstanding interpersonal relationship skills
  • Strong ability to coach and develop team members
  • Exceptional written and spoken communication skills

What You’ll Enjoy

  • Competitive salary and bonus incentives 
  • A culture of development and innovation
  • Excellent medical, dental, vision, life, long-term/short-term disability insurance, and 401k retirement plan with company match 
  • Generous paid time off, which increases annually, and paid holidays
  • Paid maternity leave
  • Ability to learn about the financial markets and trading industry from experienced professionals
  • Opportunities to work from home
  • Summer Friday (flexible) hours 
  • Great perks: team events and happy hours, paid volunteer days, catered lunches, birthday and anniversary celebrations, cereal and snack bar, and much more.

Is TopstepTrader the place for you? If so, apply today! We can’t wait to hear from you.

Direct applicants only, no recruiters, please.

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Technology we use

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We have a cool loft space close to Union and Ogilvie stations, lots of great lunch and happy hour places, and even a park! #frenchmarketfridays

An Insider's view of TopstepTrader

What's something quirky about your company?

We have some quirky debates that people are really passionate about. Cinnamon in coffee and the Oxford comma are two long-running ones that get heated. Our most recent debate was whether or not a hotdog is a sandwich! We spent a whole lunch hour debating, and the best part was that, no matter your opinion, you had a chance to make yourself heard.


Customer Support Rep

What kinds of technical challenges do you and your team face?

We have an exciting challenge to parallelize how we collect and process trading data. It's important for each user to know their account performance before the next trading day, which is less than 2 hours after trading close. Updating, collecting, and evaluating to be more efficient will enable us to take on more users and trading platforms.


Software Developer

How has your career grown since starting at the company?

At Topstep, I was encouraged to pursue my interests and not just ‘stay in my lane’. As a support rep, I had the unique opportunity to learn everything about our product and users while familiarizing myself with our tech stack in my free time. Now, as a business analyst, I get to combine these skills and help the company decide what to build next.


Business Analyst

What unique initiatives do you have that encourage innovation?

An exciting aspect about working at TopstepTrader is our commitment to Innovation. The company conducts a monthly Innovation Lab and my team (Marketing) has a weekly Innovation Hour-either meeting together to take advantage of group think or it’s self-directed. We continue to outpace the industry as the concept is so ingrained in our belief system!


VP of Marketing

How would you describe the company’s work-life balance?

As someone who recently had her first child, I can only describe TST’s work-life balance as fantastic and flexible! I know exactly what is expected of me, so if an emergency comes up and I need to leave to take care of my child, or spend some extra time with him, I’m met with encouragement and understanding instead of opposition or guilt.


HR Manager

What are TopstepTrader Perks + Benefits

TopstepTrader Benefits Overview

We believe in the well-being of our team, so we always look for more ways to reflect that in our benefits package, and company perks. Along with expected health and life insurance coverage, we offer a generous paid family leave, 401(k) match of 4%, 8 paid volunteer hours, a professional development budget for each team member, and our leadership team is extremely accessible. Not only that, but we’re ahead of the game when it comes to an inclusive environment for our diverse team, as well as an innovative culture (hint: they’re two of our 6 stated company values, and we live them).

Health Insurance & Wellness Benefits
Flexible Spending Account (FSA)
Disability Insurance
Dental Benefits
Vision Benefits
Health Insurance Benefits
Life Insurance
Retirement & Stock Options Benefits
401(K) Matching
Topstep's 401(k) retirement plan matches 100% of an employee's contributions up to 4%.
Performance Bonus
We have an Employee of the Month - who we call our Topstepper - awarded for performance while living our values, plus we have a discretionary performance bonus which is distributed twice annually.
Child Care & Parental Leave Benefits
Generous Parental Leave
At one year of service: Up to 13 weeks paid leave for primary caregiver + four weeks paid leave for the secondary caregiver + extra PTO days for both + flexible ramp up period upon return!
Flexible Work Schedule
Topstep offers a flexible schedule for most roles and is also very collaborative. We offer Summer Fridays, work from home, and are generally flexible to support your life.
Vacation & Time Off Benefits
Generous PTO
Paid time off - starting at 15 days and increasing annually - plus paid holidays, sick days, and floating holidays. The best is a $500 bonus for taking 5 consecutive PTO days!
Paid Volunteer Time
We believe that Giving Back Moves Us All Forward (one of our 6 values), so we offer each team member 8 VPTO hours to use as they wish. We also volunteer as an entire company one day each year!
Paid Holidays
Paid Sick Days
Perks & Discounts
Beer on Tap
Casual Dress
We trust all team members to Dress For Your Day so, get as casual as you like! Slippers are a must-have during the winter.
Commuter Benefits
Company Outings
Monthly FUNCtions and dept outings, killer annual holiday parties, celebrations galore, Step Up Day, new hire happy hours, and the list goes on.
Stocked Kitchen
Topstep has a fully stocked kitchen including unlimited snacks, Starbucks coffee, Tiesta Tea and all of the Starburst and M&Ms you can handle.
Some Meals Provided
Happy Hours
Recreational Clubs
Some recent examples are: 12" softball league, bocce ball, and shuffleboard at Royal Palms. We're always open to new ideas so, start something!
Professional Development Benefits
Job Training & Conferences
In addition to career coach access and quarterly team learning events, we also offer each team member a professional development budget to use as they wish.
Diversity Program
We started our D&I Committee in March '17 and today have six sub-committees to focus on hiring practices, training, cultural days of awareness and celebration, and major events, like Int'l Women's Day
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