Jobs › Direct Supply

Vice President, Finance - Business Partnership

Direct Supply · Milwaukee, WI · Full time

Posted Sep 29, 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 time your financial analysis changed how a business allocated resources.

What they are checking: Whether their partnership actually shapes decisions rather than just reporting results.

How do you build a strong, future-ready finance leadership team?

What they are checking: Talent development and succession thinking, which the posting lists explicitly.

Tell me about a difficult trade-off you helped executives make between short-term results and long-term investment.

What they are checking: Judgment on balancing speed, risk and long-term outcomes in financial decisions.

What would you do

A business leader wants to fund a pet project that the numbers do not support. How do you handle it?

What they are checking: Courage to challenge leaders with data while keeping a working partnership.

How would you change finance work itself using AI and automation?

What they are checking: Whether they will redesign finance workflows, as the posting asks under designing work systems.

How would you set up the partnership between finance and the many businesses and functions you support?

What they are checking: Ability to design a consistent business partnership model across a varied company.

About the work

As the senior finance partner to the CIO, how would you help leaders understand technology economics and ROI?

What they are checking: Ability to make technology spending understandable and accountable, a central part of the role.

Walk me through how you evaluate a large technology investment when the benefits are uncertain.

What they are checking: A disciplined approach to investment decisions with ranges, milestones and clear assumptions.

How do you measure the return on AI investments, which can be hard to pin down?

What they are checking: Practical thinking about valuing AI initiatives, since the company is AI-first.

How do you connect business performance results to actions leaders can take next quarter?

What they are checking: Ability to turn financial insight into concrete operating decisions.

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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 Vice President, Finance - Business Partnership position, you’ll lead Finance Business Partnership across Direct Supply’s businesses and key functions, strengthen financial and investment decision-making, and serve as the senior financial business partner to the CIO and Technology organization. You’ll help leaders connect business performance, resource allocation, ROI, and technology economics to action while developing a strong, future-ready Finance leadership team. Skills Needed: • Set Direction & Strategy - Define where we are heading, why it matters, and what is needed to achieve results. Turn ambiguity into clear priorities, connect day-to-day work to strategy, and focus teams on the highest-impact opportunities. • Exercise Judgment & Own Decisions - Make sound decisions by balancing data, context, risk, speed, and outcomes. Use critical thinking to evaluate ideas, AI-generated insights, and tradeoffs. Take ownership for decisions and results. • Design Work Systems - Create better ways for work to get done through people, processes, technology, and AI. Redesign workflows, clarify roles, remove friction, and build scalable work systems that improve quality, speed, customer experiences, and results. • Mobilize Leaders & Teams - Build trust and influence leaders, stakeholders, and teams around shared priorities and outcomes. Navigate relationships, organizational dynamics, and competing perspectives to build commitment, remove barriers, and drive coordinated action. • Lead & Build Capability - Inspire, develop, and enable people, teams, and systems to continuously improve. Build the skills, habits, tools, and culture needed to raise the bar and scale impact over time. What You’ll Do and Impact: • Lead the Finance Business Partnership organization across Direct Supply’s businesses and key functions, strengthening financial leadership, business acumen, accountability, and enterprise thinking. • Serve as a senior financial partner to General Managers and executives, connecting strategy, operating decisions, and financial performance to underlying economics and actionable decisions. • Partner with business leaders to identify performance gaps, opportunities, and risks early, strengthening accountability for financial commitments, forecast quality, and business performance. • Establish practical financial frameworks for significant investments and resource allocation, ensuring ROI, risks, alternatives, and expected outcomes are understood and appropriately evaluated. • Strengthen post-investment accountability by evaluating realized ROI and business outcomes against expectations and applying those learnings to future decisions. • Serve as the senior Finance partner to the CIO and Technology leadership team, providing financial leadership across Technology costs, investments, prioritization, and resource allocation. • Strengthen Technology and Product investment decisions by evaluating ROI and the economics of technology and AI, including cost-to-serve, scalability, pricing, margin, consumption costs, and emerging business models. • Lead, coach, and develop the Finance Business Partnership organization, including multiple Director-level leaders, while building succession depth and raising Finance talent capabilities. • Develop Finance leaders who combine financial acumen, business judgment, strategic influence, and AI fluency and who effectively develop the talent within their teams. • Champion Finance Transformation through technology, AI-enabled workflows, automation, and redesigned ways of working that increase capacity and improve decision quality and speed. • Partner with FinOps, Corporate FP&A, Technology, and analytics teams to implement scalable financial workflows, tools, data capabilities, and decision-support systems. Experience: • Bachelor’s degree in Finance, Accounting, Economics, Business, or a related field. • 20+ years of progressive Finance experience, including significant leadership responsibility in FP&A, Finance Business Partnership, or operational finance. • Demonstrated success leading senior Finance talent and partnering with General Managers, CIOs, executives, and other senior functional leaders. • Strong financial and business acumen with demonstrated judgment across business performance, ROI, investment decisions, resource allocation, and technology economics. • Proven ability to influence without authority, constructively challenge senior stakeholders, navigate complex organizations, and balance trusted business partnership with an enterprise-first perspective. • Strong executive communication skills and fluency with modern analytics, automation, and AI capabilities. Additional Items of Interest: • MBA, CPA, or other advanced credentials. 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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