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Venture Capital Analyst

DRW · Chicago, IL · $130,000–$160,000 a year · Venture Capital

Posted Aug 19, 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 built a financial model from scratch. What assumptions mattered most?

What they are checking: Quantitative skill and whether they know which inputs drive the answer.

The role needs a strong sense of self-motivation. Tell me about something you pursued without anyone asking you to.

What they are checking: Whether they create their own work and follow through, which a small team depends on.

Tell me about a time you had to interact with a senior executive. How did you prepare?

What they are checking: Whether they can hold their own with portfolio company leaders and co-investors.

What would you do

DRW Venture Capital invests in fintech and capital markets companies where DRW can help as a client or liquidity provider. Pick a company you would pitch to us and tell me why DRW in particular can add value.

What they are checking: Whether they understand the strategic angle of this fund, not just generic startup investing.

A founder you like has numbers that do not support the valuation they want. How do you handle it?

What they are checking: Ability to stay objective and communicate honestly while keeping the relationship.

What is a fintech investment that you think went wrong, and why?

What they are checking: Ability to learn from failures and spot risks, not just praise winners.

About the work

Walk me through how you would evaluate a Series B fintech infrastructure company.

What they are checking: A structured view of market, team, product, unit economics and terms, which is the core of the job.

How would you value a growth-stage company that is not yet profitable?

What they are checking: Familiarity with revenue multiples, comparables and scenario thinking when cash flow models do not work yet.

The portfolio includes companies like Kraken, Alpaca and TradingView. What trends in crypto or capital markets infrastructure do you find most interesting right now?

What they are checking: Genuine knowledge of the sector and an independent point of view.

How would you monitor the performance of a portfolio company after we invest?

What they are checking: Understanding of the KPIs, board materials and warning signs that matter in ongoing monitoring.

What is the difference between a liquidation preference and participation, and why does it matter?

What they are checking: Knowledge of venture terms that change how returns are actually split.

Practice this interview out loud.

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The full job description

As published by DRW.

DRW Venture Capital is a private investor in financial and enterprise technology. Our team focuses on businesses that will benefit from our engagement beyond capital: as a client, as a liquidity provider, through our review of new products, and through our deep industry expertise. We are a stage-agnostic venture capital and growth equity investor focused on companies operating within the fintech and capital markets space. Our portfolio comprises 35 companies including Crusoe, Kraken, Alpaca and TradingView.   As an Analyst or Associate , you will have meaningful exposure to all aspects of private company investing.  The role requires a strong sense of self-motivation and quantitative skills. You will play a pivotal role in the evaluation of new opportunities and in the ongoing performance monitoring of the entire portfolio and have the opportunity to regularly interact with portfolio company senior management teams and co-investors.  In this role you’ll... • Learn from entrepreneurial colleagues that have been leading innovation in technology and financial markets for 25+ years • Play a critical role within an established platform, leveraging DRW’s position as a major market participant and technology innovator to find compelling opportunities and add value to portfolio companies • Solidify core investing skills with countless opportunities to grow responsibilities What you’ll do in this role… • Sourcing : Manage pipeline of inbound leads from co-investors, entrepreneurs, and DRW employees and generate outbound opportunities through industry research, conferences, and networking • Diligence : Prepare and present investment memos and pitch decks for new and follow-on investments based on fundamental analysis and market research • Financial Analysis : Prepare valuations for current and pipeline opportunities including DCF, public and private comparables and transaction analysis • Deal Structuring : Assist with deal structuring and the evaluation of term sheets • Value Creation : Support portfolio company management teams to develop corporate strategy, evaluate M&A opportunities, assess new business lines, and other projects as needed • Portfolio Monitoring : Monitor current investments and portfolio performance via regular valuations, cap table and waterfall analysis and tracking company performance • Industry Research : Actively read and seek out new information sources to stay abreast of industry trends. Prepare analysis and research work for the group   You will be right at home if you have…  • 1 - 4 years of experience in Venture Capital, Growth Equity or Private Equity. Determination of Analyst or Associate level will be based on experience • Additional experience in Investment Banking, Consulting, Corporate Strategy or other finance role preferred • A Bachelor’s degree in Finance, Business or related field • Previous exposure to valuation modeling (LBOs, liquidation waterfalls, cap tables, DCF, etc.) and a high level of proficiency in Excel • A strong passion for investing and evaluating investment opportunities both quantitatively and qualitatively • Limitless curiosity about business models and understanding how companies make money • Strong attention to detail • A strong sense of urgency and self-motivation • An interest in the fintech investment category and in gaining exposure to companies across that landscape including cryptocurrency, trading platforms, data businesses and technology companies • Excellent communication and relationship building skills The annual base salary range for this position is $130,000 to $160,000 depending on the candidate’s experience, qualifications, and relevant skill set. The position is also eligible for an annual discretionary bonus. In addition, DRW offers a comprehensive suite of employee benefits including group medical, pharmacy, dental and vision insurance, 401k (with discretionary employer match), short and long-term disability, life and AD&D insurance, health savings accounts, and flexible spending accounts. For more information about DRW's processing activities and our use of job applicants' data, please view our Privacy Notice at https://drw.com/privacy-notice . California residents, please review the California Privacy Notice for information about certain legal rights at  https://drw.com/california-privacy-notice   #LI-DW1

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