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Senior Business Reinvention Engineer

Direct Supply · Milwaukee, WI · Full time

Posted Aug 26, 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 a cross-functional transformation you led. What business value did it deliver and how did you measure it?

What they are checking: Proven delivery of measurable value from transformation work, which the posting stresses.

Tell me about a time you learned something well outside your specialty to solve a problem.

What they are checking: Learning agility, which the posting lists first among needed skills.

How do you use AI to speed up your own learning and analysis?

What they are checking: Practical personal use of AI, which the posting encourages.

What would you do

A team you are helping is attached to its current process and resists the redesign. What do you do?

What they are checking: Influence and collaboration across boundaries, which the posting names directly.

How would you spot upstream and downstream effects before changing a workflow that touches several teams?

What they are checking: Systems thinking that avoids fixing one area while breaking another.

A redesigned workflow launches but results fall short of the target. How do you respond?

What they are checking: Ownership and iteration when results lag, rather than declaring victory at launch.

About the work

Walk me through how you would map a critical workflow before redesigning it with AI or automation.

What they are checking: Whether they understand current state and root causes before building solutions.

How do you build and own a transformation roadmap that leaders trust?

What they are checking: Ability to plan, sequence and communicate multi-step change with clear milestones.

How do you decide which parts of a workflow should be automated and which need a human?

What they are checking: Judgment on human review and exception handling in automated workflows.

What tools or platforms have you used to build automations or AI-powered workflows?

What they are checking: Whether they can build the automations themselves, since this role expects hands-on technical depth behind transformation plans.

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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 Senior Business Reinvention Engineer position, you’ll lead high-impact, cross-functional transformation initiatives that reimagine how Direct Supply operates. You’ll turn complex business challenges into scalable solutions, own transformation roadmaps, and apply AI, automation, and data to redesign critical workflows and deliver measurable business value. Skills Needed: • Learn & Adapt - Continuously grow and adapt as technology, customer needs, roles, and work systems evolve. Stay curious, learn beyond your core specialty, experiment with new approaches, use AI to accelerate learning, and improve through feedback and setbacks. • Systems Thinking & Problem Solving - Identify the right problems to solve by understanding the broader system – customers, stakeholders, processes, data, technology, and AI. Connect root causes, dependencies, tradeoffs, and upstream and downstream effects to develop practical, scalable solutions that improve the whole. • Influence & Collaborate - Build trust, communicate clearly, and work across boundaries to drive action and shared outcomes. Seek and integrate different perspectives, contribute ideas, work through dependencies, and help teams make progress together through change and ambiguity. • Apply Judgment - Make sound decisions by evaluating data, context, assumptions, risk, and outcomes. Critically assess ideas and AI-generated outputs, consider interdependencies, voice a clear point of view, and own the results and impact. • Create & Shape Ideas - Generate, test, and develop new ideas into useful, high-quality solutions and experiences. Use creativity, curiosity, technology, and different perspectives to see around the corner, innovate and develop ideas into outcomes that create value and scale. What You’ll Do and Impact: • Transform ambiguous business challenges into clearly defined opportunities, future-state designs, business cases, and executable transformation plans. • Design and deliver complex, technology-enabled solutions that reimagine end-to-end business capabilities and workflows and drive measurable business outcomes. • Own transformation roadmaps by defining priorities, sequencing initiatives, managing dependencies, and aligning business and technology teams. • Influence senior leaders to align priorities, secure sponsorship, make key decisions, and remove barriers to transformation. • Leverage data, performance insights, and business outcomes to identify opportunities, measure impact, and continuously improve solutions. • Drive visibility, stakeholder alignment, and accountability from initial concept through implementation and adoption. Experience: • Bachelor’s degree in Business, Information Systems, Engineering, or a related field. • 8+ years of experience leading complex, cross-functional business transformation, product, process, or technology-enabled initiatives, including defining future-state solutions and delivering measurable business outcomes. • Experience implementing intelligent automation, AI use cases, or integrated technology solutions across business functions such as supply chain, finance, or customer operations. • Experience applying AI, automation, workflow platforms, low-code solutions, and other emerging technologies to solve complex business problems. • Demonstrated ability to develop and present business cases tied to operational improvements, measurable value, and ROI. • Experience working within agile or hybrid delivery methodologies, including iterative development and stakeholder engagement. Additional Items of Interest: • Experience developing strategic transformation roadmaps and leading initiatives from concept through adoption. • Ability to translate complex technical concepts into clear business implications and recommendations for technical and non-technical audiences. • Experience scaling automation or technology-enabled transformation initiatives across an organization. • Lean Six Sigma, automation technology, or related certifications. 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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