Jobs › Fidelity Investments

Vice President/Associate Director, Direct Lending (Originations, Underwriting & Portfolio Management)

Fidelity Investments · Chicago, IL · $100,000–$200,000 a year · Full time

Posted Sep 24, 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 deal you passed on. Why, and how did you tell the sponsor?

What they are checking: Credit discipline balanced with relationship management, which the posting stresses.

Tell me about a time you presented a credit to an investment committee and got pushback.

What they are checking: How they defend analysis, take challenge and refine a recommendation under scrutiny.

Why do you want to join a growing team rather than an established direct lending shop?

What they are checking: Whether they truly want the responsibility and ambiguity that come with building a new strategy.

What would you do

A portfolio company misses its projections two quarters in a row. What do you do?

What they are checking: Portfolio management instincts, including early engagement with the sponsor and protecting recovery.

How would you source new deals for a newer lending platform competing with established players?

What they are checking: Entrepreneurial origination thinking and understanding of sponsor relationships in middle-market lending.

About the work

Walk me through how you would underwrite a senior loan to a middle-market company for a private equity LBO.

What they are checking: Core credit underwriting, including cash flow, leverage, sponsor quality, structure and downside cases.

What covenants and structural protections matter most to you in today's middle-market lending environment?

What they are checking: Their understanding of documentation and how lender protections have shifted in competitive markets.

How do you build a model to test a borrower's ability to service debt under stress?

What they are checking: Modeling skill, especially sensitivity and downside scenarios on EBITDA and liquidity.

How do you think about portfolio diversification across industries and sponsors?

What they are checking: Portfolio construction awareness that supports risk-adjusted returns above the market.

How would you evaluate the quality of EBITDA adjustments a sponsor puts in a deal model?

What they are checking: Skepticism and diligence on add-backs, a frequent source of hidden risk in leveraged loans.

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. Summary Fidelity Investments established a new Chicago-based lending team in 2021 to pursue private credit investing. Our leveraged finance platform targets middle-market private equity backed businesses seeking financing for LBO’s, acquisitions, dividends and other investments. We are looking for investor-minded, entrepreneurial, and accomplished candidates looking to join a growing team, gain significant experience and responsibility quickly, and help leverage the Fidelity name in this growing market. The Role Based in Chicago, this is an opportunity to join a team for the newly formed middle market direct lending strategy of Fidelity’s High Income & Alternatives group. This is a new important strategy for Fidelity where you will be a key member of the investment team. This individual will be responsible for supporting senior debt origination, underwriting and portfolio management capabilities within the broader direct lending group. This includes support of the firm’s effort to construct and lead high quality, diversified senior loan portfolios that exceed market risk-adjusted returns, and evaluation and execution of financing opportunities in a manner that balances strong credit disciplines with a positive customer relationship approach. Success in this role will require excellent work ethic, a self-starter mentality, and the ability to work independently, while also collaborating within a growing team. Successful Vice Presidents/Associate Directors will be primary candidates for promotions as the team continues to grow. Responsibilities The Vice President/Associate Director will lead and actively contribute to all aspects of origination, due diligence, and relationship/portfolio management. These responsibilities include, but are not limited to: • Leading underwriting processes, which includes analyzing and summarizing all due diligence materials related to the credit quality of businesses, specifically the analysis of the company’s historical and present financial condition, products and/or services, sales and marketing strategies, customer and supplier base, industry dynamics, competitive position, management team, and financial projections • Actively communicate with investment bankers, company management and private equity sponsors • Working with internal and external legal counsel regarding investment documentation • Becoming a subject matter expert on key private credit strategies and an advocate for the firm • Monitoring trends in the market and proposing solutions in response Qualifications We are seeking candidates who have the following characteristics: • Bachelor’s Degree in a relevant field required, advanced degree a plus • 6-10 years of experience in leverage finance, preferably with a top tier alternative lending platform • Advanced financial modeling skills and comfort dealing with a variety of capital structures • Leadership skills and ability to think strategically and creatively • Ability to create compelling, thoughtful, and creative presentation materials • Excellent written and oral communication skills • Collaborative and proactive personality The Group Fidelity’s High Income & Alternatives division brings deep investment expertise across non-investment-grade corporate credit, emerging markets debt, and real estate debt. Our platform spans the full capital structure, offering investment solutions in high-yield bonds, leveraged loans, convertible securities, and equities, with capabilities across both public and private markets. In addition to our core offerings, we provide a range of specialized strategies, including tactical asset allocation, structured credit, and liquid alternatives arbitrage strategies. Our division is distinguished by a fully integrated, highly experienced team that leverages Fidelity’s robust research platform and advanced risk management capabilities. Together, we focus on delivering innovative, adaptable investment solutions designed to meet the evolving needs of our clients and institutional partners. #FidelityAlts 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 $100,000 - $200,000 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: Category: Investment Professionals

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