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Program Manager - Spend Management

Direct Supply · Milwaukee, WI · Full time

Posted Aug 11, 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 pilot you ran that you later turned into a scaled program. What made it ready to scale?

What they are checking: Whether they know the difference between a promising pilot and something truly ready to operationalize.

Describe a time you started a program with almost no defined process. How did you create structure?

What they are checking: Whether they can build order from ambiguity while keeping work moving.

Tell me about a calculated risk you took that didn't pay off. What did you learn?

What they are checking: Whether they take smart risks with an entrepreneurial mindset and grow from the misses.

What would you do

How do you decide when to stop a pilot that isn't working?

What they are checking: Whether they set clear success criteria up front and have the discipline to end efforts that miss them.

You're coordinating product, technology, operations, and customer success. Each team says your program isn't their top priority. What do you do?

What they are checking: Whether they can earn commitment across teams through clear value and leadership support rather than pressure alone.

What would you want to learn in your first month about how Spend Management works today?

What they are checking: Whether they would listen and understand the current state before redesigning it.

How do you keep a program moving when a key stakeholder goes quiet or changes priorities?

What they are checking: Whether they have practical ways to keep momentum and escalate appropriately without losing the relationship.

About the work

Walk me through how you'd set up an intake process for new ideas so the best ones get piloted and the rest get a clear answer.

What they are checking: Whether they can create fair, simple structure around innovation without strangling it in paperwork.

What does good governance look like for an innovation program, and where does governance go too far?

What they are checking: Whether they can balance control and speed, which is the central tension of this role.

How would you report program progress to executives so they get the real picture, including risks?

What they are checking: Whether they communicate honestly and clearly upward, especially about problems, rather than just reporting green.

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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 Program Manager, Spend Management position, you’ll lead the design and execution of high-impact programs that drive innovation and scale across Spend Management. You’ll formalize how teams explore, pilot, and operationalize new ideas, creating structure around intake, execution, and governance. Partnering across product, technology, operations, and customer success, you’ll coordinate cross-functional efforts to turn strategic concepts into scalable outcomes. Skills Needed: • Deals with Ambiguity – Adapts smoothly to change and thrives in ambiguity, maintaining composure and productivity. Maintains progress despite incomplete information and tackles complex issues constructively. • Communicates Effectively – Develops and delivers impactful communications for diverse audiences across channels. Excels in both small and large group interactions. Captures attention, actively listens, and guides discussions towards targeted goals. • 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. • Collaborates Effectively – 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. • Strong program management expertise with a proven ability to lead complex, cross-functional initiatives from concept to execution. • Deep fluency in agile and OKR frameworks to drive transparency, alignment, and measurable outcomes. • Skilled at influencing without authority , guiding prioritization, governance, and resource planning across teams. What You’ll Do and Impact: • Design and implement scalable program structures for intake, governance, stage-gating, and reporting. • Collaborate with leadership to define and evolve the program lifecycle. • Drive discovery and alignment on scope, timelines, and objectives for new programs. • Develop frameworks and materials that guide prioritization, decision-making, and resource allocation. • Lead cross-functional pilot execution and scale-up decisions. • Leverage OKRs and agile principles to track progress and increase visibility. • Analyze program data to inform decisions, surface risks, and weigh tradeoffs. • Serve as program lead for strategic initiatives, ensuring delivery of key milestones and outcomes. • Build alignment and collaboration across Product, Technology, Engineering, Operations, Marketing, and Success teams. • Contribute to strategic planning and roadmap development with Spend Management leadership. • Champion an AI- and automation-first mindset across all programs and processes. Experience: • Bachelor’s degree in Business, Technology, Operations, or a related field • 7+ years of experience leading cross-functional programs, ideally in tech, operations, or platform-based environments • Strong knowledge of agile, OKRs, and strategic planning frameworks • Proven success designing pilots and scaling initiatives across internal and external teams • Effective communicator with strong facilitation and organizational skills • Experience supporting supplier- and customer-facing initiatives Additional Items of Interest: • PMP, Agile, or other program management certification preferred. • Background in supplier networks, digital platforms, or spend analytics a plus. 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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