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Volatility Trader

Simplex Trading · Chicago, IL · $150,000–$200,000 a year · Trading

Posted Sep 11, 2026 · We last checked this listing on Oct 6, 2026

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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

Tell me about a trade idea you developed from research. What was the edge and how did it play out?

What they are checking: Whether they have a real process for finding dislocations and honest results to show for it.

Tell me about your biggest trading loss. What did you change afterward?

What they are checking: Whether they learn from losses and adjust process, rather than blaming luck.

Simplex is fully in-office and collaborative. How do you share ideas with traders and technologists day to day?

What they are checking: Whether they work openly with a team instead of guarding ideas as a solo trader.

What would you do

You will work with our market making team to build systematic pricing overlays. How would you turn a discretionary view into something systematic?

What they are checking: Whether they can codify judgment into rules that a pricing system can use reliably.

You are long a big volatility position and the market moves sharply against you on unusual order flow. What do you do?

What they are checking: Calm risk management under pressure and the discipline to act on a plan rather than hope.

How would you improve hedging for a market making book that is losing edge on its hedges?

What they are checking: Practical thinking about hedge timing, cost and slippage, which directly drive profit.

About the work

How do you think about implied versus realized volatility when deciding whether an option is cheap or expensive?

What they are checking: Core volatility valuation skill and whether they know when the comparison misleads.

Walk me through how you would price an event, like earnings, into the term structure.

What they are checking: Whether they can separate event variance from base volatility, a key skill in options pricing.

What causes skew to steepen or flatten, and how would you trade a view on it?

What they are checking: Understanding of skew surface dynamics and how to express a view with controlled risk.

How do you read counterparty behavior and order flow when managing a live position?

What they are checking: Awareness that who is trading and why changes the meaning of price moves.

Give me a relative value or cross-asset volatility trade you find interesting and explain the risks.

What they are checking: Breadth of thinking across products and whether they see the hidden risks in a spread trade.

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The full job description

As published by Simplex Trading.

Our employees are our greatest asset. We have spent years building a team of talented, dedicated technologists, data-driven traders, and expert leaders with an emphasis on our core pillars: People, Process, Trading Edge, and Technology. Simplex is an in-office organization, helping to foster a collaborative and communicative culture. Position Summary As a Volatility Trader at Simplex, you will take an analytical approach to identifying market opportunities with favorable risk-reward profiles with the goal of generating trade ideas and enhancing our core market making pricing systems.  We expect that you have experience thinking about volatility valuation through a variety of lenses, including analysis of implied-vs-realized, term structure and event pricing, skew surface dynamics, and relative value or cross-asset relationships.  You will manage discretionary positions and work closely with our existing market making team to create systematic pricing overlays and improve hedging, risk management, and edge capture. Key Responsibilities • Conduct research to identify market dislocations, mispricings, or other trading opportunities in the volatility space. • Monitor and manage live positions with a focus on order flow dynamics and counterparty behavior. • Work closely with Simplex's core market making team to develop systematic approaches to volatility valuation or pricing overlays. • Continuously improve the firm's toolset for volatility research, risk management, and P&L attribution. • Clearly communicate and document research methodology and trading decisions for collaboration and review. Required Qualifications • Minimum 3–5 years of professional experience in a volatility trading/research or portfolio management role. • Demonstrated track record of generating and executing profitable trading ideas. • Strong practical foundation in options theory and Bayesian statistics/probability. • Strong analytical judgment under uncertainty; able to operate decisively under constraints. • Precise technical communication skills; able to concisely present conclusions and articulate associated inputs, assumptions, and process. • Sufficient technical skills to independently interface with data and prototype research ideas. Annual base salary ranges from $150,000 to $200,000, and is influenced by a number of factors, including qualifications and experience. This role is also eligible for an annual discretionary bonus, of which can be a significant portion of total compensation. This full time role is also eligible for other forms of compensation and benefits including health/dental/vision insurance, and 401(k) contributions. Algorithmic Trader pay range $150,000 — $200,000 USD Why us? Founded in Chicago in 2004, Simplex is a leading, technology-driven, proprietary market-making firm. We work with the most advanced technology and software in the market, and we’ve continued to remain at the forefront of the industry by always focusing on innovation, automation, and data-driven analysis. We also leverage our experience and expertise to make strategic investments and capitalize on opportunities in the venture capital markets with promising, early-stage financial and technology start-ups.  PLUS, the goods! • Benefits: Excellent a la carte Medical/Dental/Vision (free employee coverage!), 401(k) match, generous parental leave! • The Office: The kitchen is stocked with snacks, and beverages; you also have daily stipends for breakfast and lunch!  • Tuition Reimbursement: As an investment in our employees’ careers and the company’s future, we offer educational assistance to provide employees with professional development opportunities that increase their skills and enhance their contributions to the organization! • Employee Discounts: To gyms, national brands, and more! • Building:  We are located in the Federal Reserve building. As a tenant, you have access to a building gym and a full cafeteria. We are easily accessible to all public transportation. • Charity Match: We match up to $2,000 a year in donations to the charities of your choice! • Fun Events: In-person happy hours, celebrations throughout the year, game nights, video game fun, and so much more! Simplex is an Equal Opportunity Employer. Simplex and its recruitment partners may use artificial intelligence (AI) tools to support certain aspects of the recruiting and hiring process. Final hiring decisions are made by humans. For all job postings, Simplex may use AI to review and analyze applications, resumes, interviews, and applicant responses.  Simplex complies with applicable federal and state laws governing AI use. Applicants may still request reasonable accommodations. For more information related to AI or to request an accommodation, please contact  HR@simplextrading.com . 

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