Staff Software Engineer

Location: Milwaukee, WI

Time Type: Full time

Job Description

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.

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