Senior Manager, Engineering

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 Manager, Engineering position, you'll lead with an AI-first approach, seamlessly blending deep technical expertise with strategic vision to drive innovation at scale. You'll optimize systems, enhance decision-making, and foster hyper-agile, globally distributed teams. As a business-savvy technologist, you'll align engineering initiatives with corporate goals while championing diversity and inclusivity, creating an environment where cutting-edge technologies and high-performing teams thrive. Your leadership will redefine collaboration, automation, and execution, accelerating innovation and delivering transformative results.

Skills Needed:

• Leverages AI & Business Insight - Leads with an AI-First mindset infusing technology into customer solutions and workflows. Harnesses the power of AI and data to cut through noise and inform decisions. Blends business savvy, financial acumen, industry knowledge, and tech expertise to set priorities.

• 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.

• Ensures a Customer Focus - Keeps our customer needs at the center; Tirelessly pushes for AI-First solutions to create customer value and evangelizes Principle #2. Taps into market and customer insights to shape priorities and make decisions.

• Drives Accountability & Results - Sets clear goals and ensures team members deliver top-notch results. Uses data and tech to boost accountability, pushing everyone to excel individually and as a team.

• Leads Through Change & Ambiguity - Navigates the unknown with confidence, steering through change and uncertainty with a clear vision and unwavering determination. Turns chaos into clarity, keeping goals firmly in sight.

• Strong foundation in software engineering principles, including object-oriented programming (OOP) and scalable system architecture.

• Expertise in Agile development methodologies, AI-enhanced CI/CD pipelines, automated testing, and infrastructure as code (IaC).

What You'll Do and Impact:

• Drive technology strategy in collaboration with senior leadership, aligning teams to deliver scalable, business-driven solutions.

• Guide teams in adopting AI-driven automation, modern engineering practices, cloud-native architectures, and CI/CD methodologies.

• Leverage real-time analytics and AI insights to inform decision-making, continuously refining the product roadmap based on performance metrics and user behavior.

• Embed customer feedback loops, usability testing, and interviews into product development to prioritize solutions that deliver measurable value.

• Foster a hyper-agile, experimentation-driven environment, enabling rapid iteration, flexible roadmaps, and quick pivots to accelerate innovation.

• Empower teams with end-to-end ownership of the product lifecycle, ensuring accountability for performance, customer satisfaction, and long-term success.

• Promote seamless cross-team collaboration using AI-powered tools, enhancing transparency, knowledge-sharing, and alignment across the organization.

• Optimize operational efficiency by identifying automation opportunities, reducing technical debt, and streamlining development workflows.

• Champion diversity and inclusion, fostering a culture of creativity, psychological safety, and inclusive design thinking in engineering solutions.

• Ensure technical excellence, security best practices, and compliance adherence throughout the software development lifecycle.

Experience:

• Bachelor's degree in Computer Science, Software Engineering, or a related field.

• 10+ years of experience in software engineering, with expertise in software design, architecture, and development.

• 5+ years of leadership experience managing technical teams in a fast-paced, AI-driven environment.

• Proven track record of delivering large-scale AI-enhanced technology projects in enterprise or SaaS environments.

• Expertise in .NET, Web, and Mobile development, with proficiency in programming languages such as C++, Java, or Python.

• Hands-on experience with modern cloud platforms (AWS, Azure, or GCP), AI-driven automation, and containerization technologies (Docker, Kubernetes).

• Demonstrated ability to drive technology adoption, streamline processes, and implement AI-led operational efficiencies.

• Experience leading customer-facing technology platforms and managing external integrations.

• Ability to identify and automate recurring support issues using AI-powered solutions.

Additional Items of Interest:

• Experience leading teams working on multi-tiered distributed platforms and relational database design.

• Strong knowledge of AI/ML, data engineering, and automation technologies.

• Familiarity with enterprise security best practices, compliance standards, and risk mitigation.

• Proven ability to drive innovation through hackathons, proof-of-concept initiatives, and rapid prototyping.