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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 Senior Software Engineer position, you’ll lead the development of intelligent, adaptive, and scalable applications by leveraging AI-powered development tools, machine learning models, and automation frameworks. Beyond writing code, you will play a key role in setting technical direction, mentoring engineers, and driving AI-first software strategies. You’ll work on a cross-functional team dedicated to creating high-quality, scalable web-based products, mobile applications, or server-based systems. As a senior engineer, you will take ownership of complex AI-enhanced solutions, influence architectural decisions, and advocate for AI-driven development methodologies. Your leadership will help the team develop a deep understanding of business context, financial trade-offs, and the strategic impact of AI-powered 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 lead 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. What You’ll Do and Impact: • Lead and mentor engineers in AI-first development methodologies and best practices. • Architect and scale AI-enhanced systems, ensuring security, scalability, and high performance. • Integrate AI-driven capabilities such as chatbot assistants, image-based diagnostics, and automated content creation into products. • Drive adoption of AI-powered engineering tools (e.g., LLM-augmented IDEs, automation frameworks) to enhance development efficiency. • Implement observability and monitoring systems to track AI application performance and ensure proactive issue resolution. • Design and optimize AI-driven APIs and microservices for seamless interaction with models, applications, and databases. • Stay engaged with AI and engineering communities, bringing cutting-edge practices and insights back to the team. • Mentor engineers on technical execution, business impact, and AI-first strategic thinking. • Balance execution speed with innovation, rapidly testing and iterating AI-driven features. • Work in an agile environment, ensuring high-quality, scalable software solutions. Experience: • 5-7+ years of software development experience, including 2+ years working on AI-powered applications or AI-integrated solutions. • Bachelor’s degree in Computer Science, Computer Engineering, or a related field. • Hands-on experience developing and deploying AI-driven applications (provide examples using models like Hugging Face or APIs like OpenAI, Anthropic). • Proficiency in Microsoft environments (Visual Studio, VS Code) and cloud services (AWS, Azure) for scalable AI applications. • Strong understanding of AI model cost optimization, infrastructure scaling, and performance tuning. • Experience integrating LLMs, agentic workflows, and autonomous AI systems into production environments. • Proven ability to mentor engineers and lead AI-first engineering transformations. Additional Items of Interest: • Contributions to open-source AI projects or AI research. • Experience with agentic AI frameworks (LangChain, AutoGPT). • Thought leadership through conferences, research, or industry engagement in AI-first development. • Expertise in AI-powered UI/UX development and human-computer interaction. • Strong proficiency in containerization (Docker, Kubernetes) and cloud-native AI deployments. • Diligence in unit testing, integration testing, and AI-driven problem-solving. 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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