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Managing Director, Head of Trading

Cresset
Chicago, IL Full Time
POSTED ON 5/15/2026
AVAILABLE BEFORE 6/13/2026

About Cresset

Cresset is a firm built by clients, for clients. As an independent, award-winning multi-family office and private investment firm, we are reimagining the way wealth is experienced. Our purpose is to help ensure that both wealth and life are fully optimized—integrated, intentional, and aligned with each client’s vision of success.


We provide access to the caliber of talent, ideas, and investment opportunities typically available to the largest single-family offices and institutions. Our approach is personalized, entrepreneurial, and client-first.


Proudly owned by our clients and employees, Cresset was built to endure. We are creating a 100 year firm—one focused on delivering an exceptional experience, not only for the families we serve but for the team that serves them. Recognized by Barron’s and Forbes among the nation’s top RIA firms, and as one of the industry’s best places to work,* Cresset is guided by long-term relationships, shared success, and a belief that wealth should serve a life well lived.


Job Summary

The Managing Director, Head of Trading will oversee the daily operations of the trading department at Cresset. This role requires a deep understanding of the financial markets, trading processes, regulatory compliance, and technology platforms. The individual will be responsible for managing a team, ensuring the accuracy and efficiency of trade execution, settlement, and reconciliation processes, driving continuous improvement initiatives to optimize operational workflows, and ownership of trading policies. This role is critical to ensuring the firm’s trading activities are executed smoothly and in compliance with all relevant regulations.


In addition to the day-to-day responsibilities depicted above, Cresset is embarking on a build out of new trading systems and processes. This role will play an integral part in shaping the new platform. We are open to hiring in Chicago, San Francisco, or Atlanta.


Key Responsibilities


Leadership & Management:

  • Lead and manage the trade operations team, providing guidance, training, and development opportunities.
  • Effectively allocate resources and cross train team on operational functions to ensure redundancies and adequate coverage.
  • Foster a collaborative team environment focused on achieving high performance and continuous improvement.
  • Establish and maintain strong relationships with internal stakeholders, including advisors and advisor practice management, investments, operations, compliance, and technology.


Trade Execution & Processing:

  • Oversee the execution of all trades, ensuring timely and accurate trade entry, allocation, and confirmation processes.
  • Monitor and manage the settlement of trades across various asset classes including equities, fixed income, and derivatives.
  • Implement and maintain best practices for trade execution to minimize errors and operational risk.
  • Oversee the correction of trade issues, including errors, allocation or settlement issues and initiating trade corrections as needed to minimize market risk.


Compliance & Risk Management:

  • Ensure all trading activities are in compliance with regulatory requirements and internal policies.
  • Identify, assess, and mitigate operational risks within the trading process.
  • Own and update trade related policies.


Technology, Systems & Data:

  • Oversee the implementation, access to and maintenance of trading platforms and related technology systems.
  • Collaborate with IT to address system issues and enhancements that improve trade operations efficiency.
  • Ensure the accuracy of data in all trading platforms
  • Evaluate and integrate new technology solutions to enhance the trading process.


Reporting & Analytics:

  • Develop and maintain key performance indicators (KPIs) to measure the effectiveness and efficiency of trade operations.
  • Generate regular reports for senior management, highlighting key trends, issues, errors, and opportunities within trade operations.
  • Provide insights and recommendations based on trade data analysis to support decision-making.


Vendor & Counterparty Management:

  • Manage relationships with external vendors, brokers, and custodians to ensure smooth trade processing, error resolution, and settlement.


Qualifications

  • Minimum of 7-10 years of experience in large scale trade operations within an RIA, asset management, or similar financial services firm. Wealth management experience is preferred.
  • Experience trading equities, fixed income, derivatives, and other instruments required.
  • Proficient in using sophisticated, high volume trade management systems at scale, with multiple custodians and counterparties.
  • Proven leadership experience with the ability to manage and develop a team.
  • Strong knowledge of financial markets, trading platforms, and regulatory requirements.
  • Excellent analytical skills with the ability to identify and solve complex problems.
  • Proficiency with Microsoft Office Suite (Word, Excel, PowerPoint, and Outlook)
  • Strong computer skills, specifically Microsoft Excel advanced functions including Pivot Tables, vLookups, etc.
  • Experience with Power BI a plus.
  • Experience with Addepar and Salesforce a plus.
  • Exceptional communication and interpersonal skills.
  • Strong attention to detail and the ability to work under pressure.
  • Demonstrated passion for delivering exceptional client service.
  • High degree of professionalism and flexibility and able to perform successfully in a service-oriented, fast-paced, high-growth and frequently changing environment and aligned with Cresset’s values and culture


What We Offer:

At Cresset, we focus on people first. As a service business, our people are our assets. Engaging our clients and employees is our highest priority. Starting base salary range: $275,000 - $325,000. Salary will be based on factors including, but not limited to, experience, licenses/certifications, industry knowledge, and geographic location. Cresset offers a competitive compensation package including an annual incentive and a benefits package to all full-time employees including medical, dental, vision, life insurance, 401(k) retirement plan, health savings accounts, short and long-term disability insurance, voluntary critical and accident insurance, and pre-tax parking and transportation programs. Aligning employee and organizational interests, all employees receive equity in Cresset.


Equal Employment Opportunity

It is the policy of Cresset to ensure equal employment opportunity (EEO) for all employees and applicants for employment without regard to race, color, religion, sex, pregnancy (including childbirth, lactation, or related conditions), national origin or ancestry, age, disability, veteran status, uniformed servicemember status, sexual orientation, gender identity, status as a parent, genetic information (including testing and characteristics), or any other characteristic protected by applicable federal, state, or local law. It is Cresset’s policy to comply with applicable laws concerning the employment of persons with disabilities, including reasonable accommodation for applicants and employees with disabilities.


*Disclosures related to awards, recognitions, and rankings available here.


Cresset refers to Cresset Capital Management, and all its respective subsidiaries and affiliates. Cresset Asset Management, LLC, also conducts advisory business under the names of Cresset Sports & Entertainment, CH Investment Partners, and Cresset Capital. Cresset provides investment advisory, family office, and other services to individuals, families, and institutional clients. Cresset also provides investment advisory services to investment vehicles investing in private equity, real estate, and other investment opportunities. Cresset Asset Management, LLC is an SEC registered investment advisor. SEC registration does not imply any specific level of skill or training.

Salary : $275,000 - $325,000

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