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Staff Software Engineer

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 set technical direction for a team. How did you get engineers to commit to it?

What they are checking: Whether they lead through reasoning and buy-in, which is the main difference at staff level.

Tell me about an engineer you mentored. What changed in how they worked?

What they are checking: Concrete mentoring impact, which the role lists as a core responsibility.

Tell me about a time you advocated for a new development practice and it did not catch on. What did you learn?

What they are checking: Self-awareness about leading change and how they adjust when advocacy fails.

What would you do

A product manager wants a feature in two weeks that you believe needs six to do safely. How do you handle it?

What they are checking: Ability to negotiate scope and risk with the business without simply refusing or caving.

Software here touches the care of seniors. How does that change the way you think about reliability and data privacy?

What they are checking: Whether they connect engineering choices to the real people affected by failures.

About the work

How are you using AI-powered development tools in your own work today, and where have they let you down?

What they are checking: Real, critical experience with AI-assisted development, not enthusiasm without judgment.

Walk me through an architecture decision you influenced where the financial trade-off mattered as much as the technical one.

What they are checking: Whether they weigh cost and business context, which the posting names explicitly.

How would you decide whether a feature in a senior living product should use a machine learning model or simple rules?

What they are checking: Judgment on when AI adds real value versus adding cost, risk and unpredictability.

Design a system that serves a web and mobile app used by thousands of senior living communities. Where do you expect it to break first as it grows?

What they are checking: System design depth and the ability to anticipate scaling limits before they hit customers.

How do you test and monitor an AI-enhanced feature so you know it is still behaving well after launch?

What they are checking: Whether they treat evaluation and monitoring as part of shipping AI, since model behavior can drift silently.

How do you keep codebases understandable for both other developers and AI coding tools?

What they are checking: Thinking about code clarity, structure and documentation as AI-assisted development becomes normal.

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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 Staff Software Engineer position, you’ll play a critical role in shaping AI-first engineering practices, setting technical direction, and driving the adoption of cutting-edge AI capabilities across multiple teams. You will influence how software is built, ensuring that AI augmentation, agentic workflows, and autonomous systems are embedded into our engineering DNA. This role involves architecting and scaling AI-powered solutions, mentoring senior engineers, and collaborating with leadership to define and execute AI-driven strategies. Your leadership will extend beyond technical execution—helping teams develop a deep understanding of business context, financial implications, and the strategic impact of AI-driven solutions. Skills Needed: • 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. • Champions Innovation – Propels teams to unlock value with cutting-edge, tech-enabled innovations. Stays ahead of the tech curve, ready to embrace the next big thing. Leads with an entrepreneurial mindset and takes calculated risks. • Leads Through Change & Ambiguity – Navigates the unknown with confidence, steering through change and uncertainty with a clear vision and unwavering determination. • Ability to mentor and influence senior engineers in AI-first development methodologies, fostering a culture of innovation and technical excellence. • Technical expertise in AI integration across natural language processing, computer vision, and generative models. • Experience in architecting scalable AI-powered solutions that align with long-term business goals and customer needs. What You’ll Do and Impact: • Define and execute the AI engineering strategy, embedding AI-first principles across teams and projects. • Architect and scale AI-enhanced systems, integrating LLMs, agentic workflows, and composable architectures. • Mentor engineers, sharing expertise in AI-first methodologies and best practices. • Lead cross-functional AI initiatives, incorporating NLP, computer vision, and generative AI into products. • Implement AI-powered developer tools to streamline development and boost efficiency. • Drive experimentation and bridge the gap between AI research and production-ready applications. • Partner with leadership to develop AI adoption roadmaps aligned with business objectives. • Ensure security, scalability, and AI observability throughout the software lifecycle. • Make key decisions on technical trade-offs, architecture, and AI tooling. Experience: • 8+ years of software engineering experience, including 3+ years leading AI-powered application development. • Bachelor’s degree in Computer Science, Computer Engineering, or related field. • Proven experience developing, deploying, and scaling AI-powered applications (provide examples of integrations using open models or APIs). • Expertise in designing AI-first architectures, including microservices, event-driven systems, and real-time AI workflows. • Hands-on experience with LLMs, agentic AI models, and autonomous AI-driven workflows. • Strong skills in AI model deployment, cost optimization, and fine-tuning. • Deep understanding of security, compliance, and ethical considerations in AI development. Additional Items of Interest: • Experience leading AI-first engineering transformations across teams. • Contributions to open-source AI projects or AI thought leadership. • Experience with agentic AI frameworks, composable AI solutions, and MLOps best practices. • Industry engagement through conferences, research initiatives, or AI-first development communities. • Cloud-native AI deployment experience (Docker, Kubernetes, cloud 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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