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Product Owner

Direct Supply · Milwaukee, WI · Full time

Posted Aug 11, 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 say no to a stakeholder's request. How did you handle it?

What they are checking: Whether they can protect focus and explain priorities without damaging the relationship.

Tell me about a decision you made quickly with limited data. How did it turn out?

What they are checking: Whether they can balance speed and analysis, making sound calls without waiting for perfect information.

Describe a time the business goal and the user need seemed to conflict. How did you resolve it?

What they are checking: Whether they can find a solution that serves both the company and the user instead of picking a side.

What would you do

Your engineers say a story is much bigger than you expected, two days before the sprint ends. What do you do?

What they are checking: Whether they can make quick scope tradeoffs with the team instead of pushing harder or hiding the slip.

How do you represent the voice of the customer when you can't talk to customers as often as you'd like?

What they are checking: Whether they find creative sources of customer insight and keep users at the center of decisions.

How do you work with engineers on technical decisions when you aren't the technical expert?

What they are checking: Whether they collaborate deeply and respect technical judgment while still owning the product outcome.

About the work

Walk me through how you turn a high-level roadmap item into stories the team can actually build.

What they are checking: Whether they know how to break work down into clear, testable stories with real acceptance criteria.

What does a high-quality backlog look like to you, and how do you keep it that way?

What they are checking: Whether they treat backlog health as an ongoing practice, not a one-time cleanup before planning.

How have you used AI tools to help with story writing, refinement, or delivery?

What they are checking: Whether they've actually applied AI-first practices in product work, as the posting asks, and know the limits.

How would you know whether a feature you shipped actually delivered value?

What they are checking: Whether they define success measures before building and follow up after release.

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The full job description

As published by Direct Supply.

Position Summary: Direct Supply is building the future of healthcare technology with industry-leading products, solutions and platforms to help improve the lives of millions of seniors and those who care for them. In the Product Owner position, you’ll play a critical role in turning product vision into reality. You’ll own the tactical execution of the product roadmap, translating high-level strategy into actionable stories. You'll ensure backlog quality, collaborate deeply with technical teams, and bring AI-first practices to optimize delivery. You’ll serve as the voice of the customer and business, ensuring product development stays aligned with company goals and user needs. Skills Needed: ​ • Provides Customer Value - Delivers cutting-edge, tech-driven solutions paired with outrageous customer service with an eye to profitability. Seizes opportunities that reward both the customer and DS, fostering robust customer relationships. • Makes Quality Decisions - Makes swift and sound decisions that propel objectives forward. Hunts for crucial qualitative and quantitative data. Balances thorough analysis with wisdom, experience, and judgment for informed decision-making. • Applies AI and Technology - Identifies opportunities to boost efficiency and add value using AI and tech. Embraces and applies digital innovations and tech solutions to build business. Eagerly learns and integrates new technologies where they matter most. • Effectively Collaborates - Forges strong partnerships and works productively with others to achieve common goals. Finds common ground to solve problems and seeks out diverse perspectives to inform decisions. Quickly earns trust, puts others at ease, and shows empathy. • Optimizes Work Processes - Streamlines workflows by harnessing data, AI, and technology. Identifies opportunities for efficiency and incorporates new processes and technology. Defines new success measures. • Strong ability to translate product strategy and roadmap into actionable development work. What You’ll Do and Impact: • Own the execution of roadmap features, managing scope and alignment to delivery timelines and business goals. • Translate product roadmap items into clear user stories with defined acceptance criteria. • Manage and prioritize the team backlog, ensuring it reflects business value, technical feasibility, and sequencing needs. • Collaborate with developers and tech leads to clarify requirements, remove blockers, and ensure delivery readiness. • Use AI-enabled tools for backlog grooming, customer insight analysis, and story creation to improve speed and quality. • Track team progress against sprint goals, identify risks early, and support the team in maintaining velocity. • Embed automation or AI functionality into features where it enhances product value or efficiency. • Partner with the Product Manager to ensure work aligns to product vision, goals, and key metrics. • Lead by example in maintaining high standards for execution, backlog quality, and delivery clarity within the team. • Communicate trade-offs and delivery updates with stakeholders in a clear and confident manner. Experience: • Bachelor’s degree in Business, Technology, or a related field. • 2+ years in a product owner, business analyst, or software delivery role. • Experience working in Agile environments with backlog management tools (e.g., Jira, Confluence, Aha!). • Familiarity with AI tools, prompt engineering, or low-code platforms is a plus. • Experience collaborating with developers and technical stakeholders. Additional Items of Interest: • Certified Scrum Product Owner (CSPO) or equivalent Agile certification. • Experience in healthcare, B2B SaaS, or digital platforms. Job to be performed in the location listed. Generous benefit package available. © 2013 to 2026 Direct Supply, Inc. All rights reserved.

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