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Staff Business Reinvention Architect

Direct Supply · Milwaukee, WI · Full time

Posted Aug 12, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about an enterprise workflow you redesigned end to end. What did the future state look like and how did you get there?

What they are checking: Real experience with large-scale workflow redesign rather than isolated automation projects.

Tell me about a time you drove adoption of an emerging technology that people resisted.

What they are checking: Change leadership for new technology, which the posting lists under applying AI.

Tell me about a transformation that failed or stalled. What would you do differently?

What they are checking: Honest reflection on what makes large change efforts break down.

What would you do

As a trusted advisor to senior leaders, how do you tell them a favored initiative will not deliver what they expect?

What they are checking: Courage and tact in advising executives, which defines a trusted advisor.

Two functions both want their workflow reinvented first, and you have capacity for one. How do you decide?

What they are checking: Strategic prioritization that ties choices to company goals.

About the work

How do you decide whether a process should be automated, redesigned with AI, or eliminated altogether?

What they are checking: Judgment that questions the process first instead of automating waste.

Walk me through how you would design a future-state integration architecture across several platforms that were never built to talk to each other.

What they are checking: Integration architecture depth, which the posting names as a core responsibility.

How do you build a transformation framework that different solution groups will actually use?

What they are checking: Ability to create repeatable methods that scale beyond the architect's own projects.

How do you measure whether a reinvention effort produced sustainable business outcomes and not just a short-term gain?

What they are checking: Focus on lasting results and clear metrics instead of launch-day wins.

What future trends in AI or automation do you think will matter most for a company serving senior living, and why?

What they are checking: Strategic thinking that anticipates trends and links them to this business.

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The full job description

As published by Direct Supply.

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 Staff Business Reinvention Architect p osi tion, you’ll serve as a senior expert driving enterprise-wide workflow redesign and future-state integration architecture. Leveraging AI, intelligent automation, and data-driven insights, you’ll reimagine how Direct Supply operates across functions and solution groups. As a trusted advisor to senior leadership, you’ll shape transformation frameworks, architect cross-platform solutions, and align strategic initiatives with company goals—ensuring the right technologies power scalable and sustainable business outcomes. Skills Needed: • Applies AI and Technology – Identifies opportunities to reinvent workflows that add customer value and boost efficiency using AI and technology. Eagerly learns and integrates new technologies where they matter most. Drives adoption of emerging technologies that enable reinvention. • 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. • Optimizes Work Processes – Streamlines workflows by harnessing data, AI, and technology. Identifies opportunities for efficiency and incorporates new processes and technology. Defines new success measures. • Navigates Organizational Dynamics – Knows how to maneuver through both formal channels and informal networks. Engages and influences stakeholders to align business priorities with transformation initiatives. Understands our DS norms and the reasoning behind them. • Proven ability to lead complex, cross-functional initiatives from strategy through implementation, ensuring solutions drive measurable business outcomes. • Strong ability to influence senior stakeholders and decision-makers , providing architectural thought leadership and strategic guidance. • Expertise in developing scalable frameworks and reusable patterns that accelerate transformation and enable enterprise-wide adoption. What You’ll Do and Impact: • Deliver scalable, maintainable solutions that drive measurable business outcomes and enterprise-wide impact • Architect and lead the implementation of end-to-end workflows that redefine operations across functions and solution groups • Drive enterprise transformation initiatives focused on AI, data, and automation to reinvent core business processes • Define and execute transformation roadmaps that align with strategic priorities and deliver quantifiable results • Design and integrate workflows across platforms including Zendesk, RingCentral, CRM, Microsoft 365, and legacy systems to enable a unified business architecture • Act as a senior advisor to executives and solution leaders, influencing enterprise strategy and securing alignment for large-scale change • Ensure cohesion between operating model design, technology strategy, and customer-centric outcomes • Develop reusable frameworks, playbooks, and templates to scale transformation practices across the organization • Champion the delivery of high-impact solutions that enhance efficiency, system performance, and organizational agility Experience: • Bachelor’s degree in Engineering , Computer Science, or related field required ; Master’s degree (MBA or technical field) preferred • 12+ years of experience in enterprise architecture, business process engineering, automation design, or digital transformation at scale • Demonstrated success architecting and delivering large-scale, cross-functional solutions that span platforms, business units, and technologies • Deep expertise in intelligent automation, RPA, low-code tools, AI applications, system integration, and workflow orchestration • Proven ability to influence architectural standards and drive alignment across engineering, product, and business teams • Strong track record of creating transformation playbooks, system diagrams, and reusable frameworks that accelerate enterprise adoption Additional Items of Interest: • Strong track record of delivering technical innovation that improves system performance and user outcomes. • Experience leading high-complexity, enterprise-wide transformation initiatives from design through implementation. • Deep technical fluency and ability to guide solution design across workflow and automation platforms. Job to be performed in the location listed. Generous benefit package available. © 2013 to 2026 Direct Supply, Inc. All rights reserved.

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