Staff Software Engineer

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. The Staff Software Engineer position plays a critical role in shaping AI-first engineering practices, setting technical direction, and driving AI adoption across multiple teams. This role advances the integration of AI augmentation, agentic workflows, and autonomous systems into software development practices to improve engineering capabilities and deliver business value. Working across engineering teams and with technology leadership, you'll architect and scale AI-powered solutions, mentor senior engineers, and help define and execute AI-driven strategies. Your technical leadership will help teams understand the business context, financial implications, and strategic impact of AI-driven solutions. What You’ll Do and Impact: Define and execute AI engineering strategies that establish AI-first practices across teams and projects. Architect and scale AI-powered systems using large language models (LLMs), agentic workflows, and composable architectures to deliver reliable, scalable solutions. Mentor engineers in AI-first methodologies and engineering best practices to strengthen technical capabilities across teams. Lead cross-functional AI initiatives that integrate natural language processing (NLP), computer vision, and generative AI into products. Implement AI-powered development tools that streamline engineering workflows and improve productivity. Drive AI experimentation and translate emerging research into practical, production-ready applications. Partner with technology leadership to develop AI adoption roadmaps aligned with business objectives and strategic priorities. Ensure security, scalability, and AI observability throughout the software development lifecycle. Make key technical decisions on architecture, AI tooling, and engineering trade-offs to support effective solution design and delivery. What You’ll Bring: Bachelor's degree in Computer Science, Computer Engineering, or a related field. 5+ years of software engineering experience, including 3+ years leading AI-powered application development. Proven experience developing, deploying, and scaling AI-powered applications 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 technical skills in AI model deployment, cost optimization, and fine-tuning. Deep understanding of security, compliance, and ethical considerations in AI development. Job to be performed in the location listed. Generous benefit package available. 2013 to 2026 Direct Supply, Inc. All rights reserved.SummaryLocation: Milwaukee, WIType: Full time