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Trading Specialist- Greater Chicago, IL Area (REMOTE)

Fidelity Investments · Chicago, IL · $44,000–$80,000 a year · Full time

Posted Sep 4, 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 time you turned a service call into a deeper relationship or a new solution for the client.

What they are checking: Whether they find opportunities to connect clients with more help without being salesy.

How do you keep up with market news and economic trends day to day?

What they are checking: Whether they stay informed enough to give useful context on client calls.

Tell me about a time you calmed an upset client about a loss in their account.

What they are checking: Whether they show empathy and stay factual when clients are emotional about money.

What would you do

The market is falling fast and calls are stacking up. How do you keep your quality high?

What they are checking: Whether they stay accurate and calm on inbound calls during volatile markets.

A client wants to trade options but is not approved. How do you handle the conversation?

What they are checking: Whether they follow suitability rules while helping the client understand the approval process.

You make an error entering a client's trade. What do you do?

What they are checking: Whether they report errors right away and follow correction procedures honestly.

This role is remote within ninety miles of a branch. How do you stay productive and connected working from home?

What they are checking: Whether they can work reliably remote while staying part of the team.

About the work

A client calls asking why their limit order did not fill even though the stock touched their price. How do you explain it?

What they are checking: Whether they understand order mechanics and can explain them clearly to a frustrated client.

Walk me through the difference between a stop order and a stop limit order.

What they are checking: Whether they know core order types well enough to guide clients during market moves.

How would you explain margin and a margin call to a client who is new to it?

What they are checking: Whether they can explain risk plainly, which protects clients and the firm.

What regulations shape how you can talk to clients about trades and investments?

What they are checking: Whether they know where education ends and advice begins under FINRA rules.

Practice this interview out loud.

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The full job description

As published by Fidelity Investments.

Job Description: NOTE: Fidelity will not provide immigration sponsorship for this position To be eligible for consideration of this role, your primary residence must be located within a 90 mile radius at the time of application from the approved branch sites: Chicago North, Chicago Gold Coast, Highland Park, Naperville, Oak Brook, Orland Park, Schaumburg The Role As a Trading Specialist, you will support investors with a broad range of trading, investment, and account-related needs while helping deepen client relationships! This role involves guiding clients through market activity, processing complex securities transactions, and providing education that helps clients make informed financial decisions. By delivering personalized support through inbound client interactions, you will build trust, strengthen client loyalty, and find opportunities to connect clients with additional products and solutions. Success in this role requires a strong understanding of financial markets, trading products, industry regulations, and proficiency in breaking down complex concepts into significant client conversations. The Expertise & Skills You Bring • Series 7 license required • Series 63 license or ability to obtain within 90 days • Experience in financial services, brokerage operations, trading support, client services, or a related field. • Knowledge of financial markets, investment products, economic trends, and industry developments. • Understanding of securities transactions, including equities, options, mutual funds, fixed income securities, and precious metals. • Ability to apply regulatory and policy requirements while delivering accurate and compliant support to clients. • Ability to guide clients through trading and investment decisions with integrity and confidence. • Consultative approach to uncovering client needs and recommending appropriate offerings, support, and solutions. • Excellent communication and active listening skills, including the ability to explain complex investment and trading concepts in a clear and relatable manner. • Strong attention to detail and commitment to accuracy when processing transactions and handling client requests. • Effective problem-solving, critical-thinking, and decision-making skills. • Ability to manage several priorities and perform effectively in a fast-paced, team-oriented environment. The Team As part of Fidelity's Client Services organization, we serve as a key connection between our clients and a diverse selection of investment products, services, and financial solutions. Our team helps investors navigate the markets by providing trading support, education, and mentorship that builds confidence and trust. We are committed to delivering outstanding service, encouraging long-term relationships, and helping clients achieve their financial goals through every market environment. Fidelity’s Onsite Working Model Fidelity is transitioning to a full-time onsite working model through a phased rollout across regions and roles. Currently, some roles and locations require 100% onsite presence, while others require less. Onsite expectations are likely to evolve as the rollout continues. This transition does not apply to fully remote roles. The base salary range for this position is $44,000-80,000 USD per year. Placement in the range will vary based on job responsibilities and scope, geographic location, candidate’s relevant experience, and other factors. Base salary is only part of the total compensation package. Depending on the position and eligibility requirements, the offer package may also include bonus or other variable compensation. We offer a wide range of benefits to meet your evolving needs and help you live your best life at work and at home. These benefits include comprehensive health care coverage and emotional well-being support, market-leading retirement, generous paid time off and parental leave, charitable giving employee match program, and educational assistance including student loan repayment, tuition reimbursement, and learning resources to develop your career. Note, the application window closes when the position is filled or unposted. Please be advised that Fidelity’s business is governed by the provisions of the Securities Exchange Act of 1934, the Investment Advisers Act of 1940, the Investment Company Act of 1940, ERISA, numerous state laws governing securities, investment and retirement-related financial activities and the rules and regulations of numerous self-regulatory organizations, including FINRA, among others. Those laws and regulations may restrict Fidelity from hiring and/or associating with individuals with certain Criminal Histories. Certifications: Series 07 - FINRA, Series 63 - FINRA Category: Customer Service

Apply at Fidelity Investments