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Operations Analyst

CSS LLC, Chicago, IL, United States


To apply, please email resume and cover letter to careers@csstrading.com.

Position Summary
We are an investment firm looking for analyst to support our firm’s operations. The person hired for this role will work closely with all members of the firm. This role is critical to the success of the firm’s trading function and requires great attention to detail and someone who takes a proactive approach to responsibilities.

Location :

Chicago. Position requires 4 days in office.

Education & Professional Skills
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Bachelor’s Degree (Finance or Accounting preferred).
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1 to 3 years of experience in financial services. Experience at an investment firm is a plus.
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Proficiency in financial and accounting concepts.
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Strong Microsoft Office skills.
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Enthusiastic approach to financial markets.
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Experience with bank debt and Clearpar is a plus.
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Comfortable using AI tools (e.g., Claude, Copilot) to automate workflows and improve efficiencies.

Key Responsibilities & Contributions
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Assist Director of Operations with daily position and cash reconciliations.
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Assist with monthly reconciliations and reporting.
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Maintain and update the security master database.
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Work with external counterparties to resolve daily trade breaks.
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Work with Portfolio Managers to book and allocate trades.
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Work with Portfolio Managers to review and input corporate actions.
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Execute asset and money transfers.
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Assist Treasury department with stock loan management.
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Understand margin methodologies across prime brokers and effectively field questions from PMs.
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Manage onboarding of new broker and accounts.
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Develop relationships with external counterparties, including prime brokers, executing brokers and vendors.

Compensation & Benefits
Compensation will be competitive and commensurate with candidate's qualifications and experience. The total compensation range for this role is $70,000–$100,000, consisting of base salary plus an annual performance-based bonus. Comprehensive benefits package including medical, dental & vision, retirement plan including firm contribution, life insurance, and gym & wellness facilities.

About CSS, LLC
We are a Chicago-based investment partnership founded in 1998. Our core strategies focus on convertible arbitrage, credit investing, and event-driven special situations. Employing a technology-driven, team-oriented approach to identify compelling investments, we strive to produce industry-leading risk-adjusted returns. We take pride in our performance, stability, reputation, and ability to allocate capital opportunistically across asset classes.