Senior Staff Software Engineer

Position Summary:Direct Supply is building the future of senior living technology, helping connect the spectrum of healthcare in order to improve the lives of millions of seniors!In the Senior Staff Software Engineer position, you’ll lead the design and delivery of highly complex, AI-driven systems across multiple teams and platforms. You will define architectural patterns, guide the strategic direction of AI-first development practices, and drive alignment across engineering domains. This role blends technical depth with cross-team leadership and requires strong business acumen to scale software solutions with measurable impact. Skills Needed: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. Leads & Inspires Partner Owners - Ignites Partner Owners’ passion and purpose. Boosts Partners to peak performance while operating at the top of their license. Attracts and develops top talent and builds an environment that fuels innovation. 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. What You’ll Do and Impact: 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. Experience:Bachelor’s degree in Computer Science, Engineering, or a related field; Master’s preferred. 10+ years of software engineering experience, including 3+ years leading architectural decisions across multiple teams or platforms. Proven experience designing and scaling AI-enhanced systems in a cloud-native environment. Deep knowledge of system architecture, performance tuning, and distributed computing. Demonstrated success mentoring engineers and influencing technical direction across functions.Job to be performed in the location listed. Generous benefit package available. 2013 to 2026 Direct Supply, Inc. All rights reserved.SummaryLocation: NC Durham Office; WI Milwaukee Main Campus; WI Milwaukee Innovation and Technology CenterType: Full time