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Product Analyst

PEAK6 · Chicago, IL · $92,000–$115,000 a year · Full time

Posted Sep 16, 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 had to create clarity in an ambiguous project.

What they are checking: Whether they can define the problem themselves, which the posting says is common in this role.

Tell me about a time you used data to change someone's mind about a product decision.

What they are checking: Whether they use analysis to persuade rather than opinion or seniority.

What would you do

The finance team says a tool is slow and frustrating. How would you figure out what's really wrong?

What they are checking: Whether they dig into user workflows and data before jumping to a solution.

You have to balance fixing bugs in existing tools with building something new. How do you decide?

What they are checking: Whether they can protect current users while still moving new work forward.

A stakeholder asks for a feature by the end of the week that you think is a bad idea. How do you respond?

What they are checking: Whether they can say no or offer alternatives while keeping the relationship strong.

About the work

How would you build a roadmap for internal HR, Finance and Support tools when users all want different things?

What they are checking: Whether they can prioritize by value and effort and explain the trade-offs to stakeholders.

How do you decide whether to buy a SaaS tool or build something in-house?

What they are checking: Whether they weigh cost, fit, integration and support burden before recommending a path.

How do you write requirements that engineers can actually build from?

What they are checking: Whether their user stories and acceptance criteria are clear enough to avoid rework.

How would you measure whether an internal tool is succeeding after launch?

What they are checking: Whether they define real metrics like adoption, time saved or error rates instead of just shipping.

How comfortable are you with SQL or other tools for pulling your own data?

What they are checking: Whether they can answer their own questions without waiting on others.

Practice this interview out loud.

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The full job description

As published by PEAK6.

WHO WE ARE We are PEAK6, a leading investment firm, using technology to find a better way of doing things. The company’s first tech-based solution was developed in 1997 to optimize options trading, and over the past two decades, the same formula has been used across a range of industries, asset classes, and business stages to consistently deliver superior results. Today, PEAK6 seeks transformational opportunities to provide capital and strategic support to entrepreneurs and forward-thinking businesses. PEAK6’s core brands include PEAK6 Capital Management, PEAK6 Strategic Capital, Apex Fintech Solutions, FOCUS, We Insure, Evil Geniuses, Poker Power, Zogo, and Bruce Markets. ABOUT THIS ROLE The Product Analyst is strategic and tactical, shaping the tools, platforms, and systems powering our growing portfolio businesses. You can seamlessly switch between big-picture vision and hands-on execution, and succeed in dynamic environments where clarity often needs to be created from ambiguity. Your day-to-day will include iterating on proven products and envisioning entirely new ones, with the goal of boosting performance, efficiency, and innovation on the desk. You'll be responsible for: • Develop and execute product roadmaps for internal HR, Finance, and Support SaaS and homegrown tools while balancing support for existing products with new innovations. • Engage directly with multiple departments to identify workflows, pain points, define needs, and create technology/ai solutions that drive business value. • Champion product vision; communicate priorities, strategy, and progress across the organization. • Define user stories, map user flows, prioritize the backlog, and set clear acceptance criteria. • Proactively build partnerships with different teams across a number of internal initiatives to surface new ideas and cross-pollinate solutions. • Implement and communicate metrics, conduct usability testing, and use data to continually improve product fit and impact. • Stay at the forefront of documentation and best practices, supporting both new and legacy product lines. YOUR EXPERIENCE • 2-4+ years of product management experience, preferably in internal, multi-tenant systems • Direct experience working with agile teams to deliver products from vision through execution. • Inquisitive and engaged in using and building AI-centric tooling and workflows. • History of success building and iterating on user-centric, mission-critical applications in time-sensitive domains. • Demonstrated ability to build deep partnerships with technical and non-technical stakeholders. • Strong communication, documentation, and relationship management skills. • Analytical mindset—comfortable working with data, defining KPIs, and rapidly assessing success/failure during product lifecycles. • Adaptability and bias for action—able to navigate ambiguity, work at speed, and drive results in highly dynamic environments. OUR REWARDS We offer a robust package of employee perks and benefits, including healthcare benefits (medical, dental and vision, EAP), competitive PTO, 401k match, parental leave, and HSA contribution match. We also provide our employees with a paid subscription to the Calm app and offer generous external learning and tuition reimbursement benefits. As a hybrid workforce, we offer our employees the ability to work remotely up to two days a week. Base pay offered may vary depending on job-related knowledge, skills, experience, and office location. This position also may be eligible for a discretionary annual bonus in addition to a range of health & wellness benefits, enhancing your overall compensation package. Base Salary Range $92,000-$115,000 PEAK6 is proud to be an equal opportunity employer that does not discriminate on the basis of race, color, religion, sex (including pregnancy, sexual orientation, and gender identity), national origin, age, disability, veteran status, marital status, or any other protected characteristic. Our hiring practices ensure that all qualified applicants receive fair consideration without regard to these characteristics. PEAK6 is committed to creating an inclusive and accessible workplace for all candidates, including those with disabilities. We are dedicated to ensuring equal employment opportunities and providing reasonable accommodations to qualified individuals with disabilities. If you require reasonable accommodations to participate in the application or interview process, please contact our HR department at hr@peak6.com. We will work with you to provide the necessary accommodations to ensure your full participation in our hiring process. #PEAK6 Application data may be reviewed, including through automated tools, for security and fraud-prevention purposes. This review is conducted by our information security team and is separate from hiring decisions

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