Senior Staff Software Engineer

Direct Supply•Milwaukee, WI

About The Position

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 Staff Software Engineer position, you’ll lead the development of complex, AI-enabled software systems across multiple platforms. You will set architectural standards, shape AI-first engineering strategies, and influence cross-functional alignment. This role blends technical depth with strategic leadership to deliver scalable, business-critical platforms with measurable results.

Requirements

Thinks Strategically - Anticipates future trends and aligns actions with long-term objectives. Draws on broad knowledge to craft future-focused plans that effectively translate strategy into action.
Applies AI & 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.
Delivers Results - Seizes new opportunities and tackles challenges head-on with urgency. Takes initiative and consistently hits goals. Zeroes in on key priorities for results. Drives progress through uncertainty and moves others to action.
Demonstrates Influence & Organizational Savvy - Wields influence with a masterful understanding of organizational dynamics, effortlessly navigating the complexities to shape outcomes and drive strategic alliances.
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.
Excellent ability to lead complex initiatives across domains, uniting architecture, development, and strategy.
Deep technical expertise in AI system architecture, including LLM integration and scalable cloud-native design.
Bachelor’s degree in Computer Science, Engineering, or related field; Master’s preferred
10+ years of software engineering experience, including 3+ years in cross-platform architecture leadership
Demonstrated success building AI-enhanced, cloud-native systems
Strong understanding of distributed systems, performance optimization, and system reliability
Proven track record mentoring engineers and driving architectural direction across teams

Nice To Haves

Experience with large-scale systems using LLMs, generative AI, or ML pipelines
Certifications in AWS, GCP, or related architecture/AI tools are a plus

Responsibilities

Lead the architecture and development of scalable, AI-powered systems that span multiple platforms and product lines
Partner with engineering and product leaders to set and drive the strategic technical direction
Guide engineering best practices across domains, ensuring consistency in design, security, performance, and reliability
Identify and evaluate emerging technologies for potential integration, including LLMs, autonomous systems, and next-gen dev tools
Act as a technical mentor, shaping the growth of senior and staff engineers through coaching and architectural leadership
Drive cross-functional initiatives that deliver measurable improvements to engineering velocity and business outcomes
While not a day-to-day coder, able to deep-dive into architecture, codebases, and design reviews when needed to resolve ambiguity or unblock teams.
Ensure architectural decisions and platform strategies enable successful delivery of business-critical initiatives with measurable outcomes.