Senior Digital Workplace Engineer

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 Digital Workplace Engineer position, you’ll architect and manage secure, scalable, and user‑centric digital workplace platforms to elevate enterprise collaboration and productivity. You’ll lead strategy and execution for Microsoft 365 services, Entra , and identity access management, while integrating AI‑powered tools like Copilot and ChatGPT into core workflows. Your work will empower over 1,300 employees to work more securely and effectively‑driving measurable improvements in access, experience, and operational efficiency.

• Provides Customer Value - Delivers cutting‑edge, tech‑driven solutions paired with outrageous customer service with an eye to profitability. Seizes opportunities that reward both the customer and DS, fostering robust customer relationships.
• Enriches Innovation - Sparks creative ideas and harnesses AI and technology to deliver tangible benefits. Champions diverse thought and boldly challenges conventional norms.
• 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.
• Learns Quickly - Rapidly absorbs and applies new information and skills and enjoys new challenges. Innovates and experiments to solve problems, reflecting on both successes and failures for growth. Is a naturally curious and adaptable learner.
• Effectively Collaborates - Forges strong partnerships and works productively with others to achieve common goals. Finds common ground to solve problems and seeks out diverse perspectives to inform decisions. Quickly earns trust, puts others at ease, and shows empathy.

• Design, implement, and optimize Microsoft 365 platforms (Teams, SharePoint, One Drive) to drive collaboration and performance.
• Manage identity lifecycle, conditional access, and device trust policies through Entra  support secure, scalable access.
• Integrate AI tools like Copilot and ChatGPT into user workflows to improve productivity and reduce friction.
• Govern Microsoft 365 tenant architecture, licensing (E5, Copilot), and platform scalability to align with cost and compliance goals.
• Automate collaboration and access workflows using Power Shell, Power Automate, and Graph API.
• Partner with Security, Support, and Client Engineering to advance Zero Trust architecture and hybrid work readiness.
• Co‑develop AI‑driven productivity solutions with Business Process Engineering and Data Science teams.
• Monitor industry trends and lead the adoption of emerging workplace technologies.
• Translate complex technical concepts into actionable strategies aligned with enterprise priorities.
• Engage with peer groups and external communities to share insights and benchmark best‑in‑class practices.

Accountable for:

• Reducing recurring access and identity support demand through automation, not added headcount.
• Automating joiner/mover/leaver provisioning on the native Workday‑to‑Entra connector.
• Making routine access self‑service, with the right controls on higher‑risk access.
• Governance, scalability, and security of the M365 tenant and Entra .
• Microsoft licensing strategy (Copilot, E5, security/compliance SKUs), getting full value before buying more.
• Putting Copilot and AI tools to work in real partner workflows.

Success looks like:

• A measurable drop in recurring access and identity tickets.
• Joiner/mover/leaver runs hands‑off for common cases; exceptions flagged, not missed.
• Routine access resolved faster, fewer escalations, audit posture held or improved.
• More value from existing Microsoft spend, with AI workflows adopted, not just available.

• Bachelor's degree in Information Technology, Computer Science, or a related field required.
• 5+ years of experience in IT infrastructure or systems engineering focused on collaboration and identity platforms.
• Demonstrated experience deploying AI‑enhanced…