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Strategy Manager

CDW · Chicago, IL · 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 the most ambiguous business problem you've worked on. How did you give it structure?

What they are checking: How they handle unclear problems, which this role states is central to the job.

Walk me through an analysis where the data pointed somewhere leaders didn't expect.

What they are checking: Whether they will deliver uncomfortable findings clearly and with enough evidence to be believed.

Tell me about a time stakeholders disagreed on the right answer. How did you help them get aligned?

What they are checking: Their ability to move people toward a decision using facts and clear trade-offs.

What's a recommendation you made that turned out wrong, and what did you learn?

What they are checking: Their honesty about mistakes and whether they adjust their judgment afterward.

What would you do

A leader asks you, "Should we expand this service line?" How do you turn that into a workplan?

What they are checking: Whether they can break a vague question into specific sub-questions, data needs and a timeline.

You need input from five departments, and two are slow to respond. What do you do?

What they are checking: Whether they can keep cross-functional work moving without authority over the people involved.

You're asked to deliver a strategy update in two days that normally takes two weeks. How do you handle it?

What they are checking: Whether they can trade depth for speed sensibly and say clearly what is still uncertain.

About the work

How do you build a recommendation slide that a busy executive can act on in two minutes?

What they are checking: Whether they lead with the answer and support it, instead of walking through all their work.

How do you check your own analysis for errors before it goes to leadership?

What they are checking: Whether accuracy is built into their process, since a wrong number damages trust in the whole team.

How would you size the market for a new IT service offering if good data wasn't available?

What they are checking: Whether they can build a reasonable estimate from assumptions and state those assumptions openly.

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The full job description

As published by CDW.

The Strategy Manager supports strategic planning, business analysis, and cross-functional execution across key organizational priorities. This role partners with stakeholders across multiple departments to structure complex business questions, analyze data, identify trends, and translate insights into clear recommendations that support decision-making. This individual will help structure ambiguous business questions, develop clear workplans, gather and synthesize inputs from cross-functional partners, and communicate recommendations through presentations, written updates, and verbal discussions. The Strategy Manager will work closely with leaders and business partners to drive work forward, support alignment, and ensure strategy deliverables are completed with accuracy, clarity, and pace. The ideal candidate is a proactive problem solver with strong communication skills, sound business judgment, and the ability to navigate ambiguity while driving work to completion. What you'll do • Partner with cross-functional stakeholders to support strategy initiatives, business planning efforts, and key projects aligned to department and organizational priorities. • Break down complex or ambiguous business questions into structured workplans, analyses, and recommendations. • Analyze data, identify trends, and synthesize insights to support business decisions and strategic recommendations. • Develop clear, professional presentations, memos, and written communications for a variety of audiences, including senior leaders and executive stakeholders. • Gather inputs from teams such as Finance, Operations, Product, Commercial, Marketing, and other business functions to help inform recommendations. • Facilitate working sessions, project discussions, and stakeholder updates to drive alignment and move work to completion. • Support the development of business cases, scenario analysis, market assessments, and other strategic deliverables. • Distinguish key insights from available data and clearly communicate what the analysis supports. • Manage priorities, timelines, and deliverables to ensure work is completed accurately and efficiently. • Build strong working relationships across departments and act as a trusted partner in helping teams solve business challenges. What we expect of you • Bachelor degree and 5 years of experience in strategy, business analysis, consulting, finance, operations, corporate planning, or a related business function OR • 9 years of experience in strategy, business analysis, consulting, finance, operations, corporate planning, or a related business function Preferred skills, experience, and qualities needed • Demonstrated experience structuring complex problems, analyzing information, and developing clear business recommendations. • Strong written and verbal communication skills, with the ability to communicate effectively and professionally across all levels of the organization, including senior and executive leadership. • Proven ability to collaborate with a wide range of stakeholders across multiple departments. • Strong analytical skills with the ability to interpret data, identify trends, and translate insights into actionable recommendations. • Ability to manage multiple priorities, drive work to completion, and adapt to changing business needs. • Demonstrated ability to take ownership of responsibilities, navigate ambiguity, and work independently with appropriate guidance. • Proficiency in Microsoft Office applications, including PowerPoint and Excel. • Experience working in a large corporate environment or on a strategy-focused team. • Experience in management consulting, corporate strategy, business operations, finance, or a related strategic function. • Foundational understanding of finance, business metrics, P&L concepts, or business case development. • Experience developing executive-ready presentations, business updates, or strategic recommendations. • Strong planning and execution skills, with the ability to demonstrate a strategic thought process. • Ability to influence, collaborate, and build trusted relationships across teams. • Strong organizational skills and attention to detail. • Comfortable working through ambiguity and bringing structure to undefined or evolving priorities. • Adaptable, coachable, and eager to learn and grow within the role. • Experience in B2B technology, commercial strategy, operations, or an adjacent industry preferred. Pay range: $125 ,000 - $174 , 6 00 depending on experience and skill set Annual bonus target of 10 % subject to terms and conditions of plan Benefits overview: https://cdw.benefit-info.com/ Salary ranges may be subject to geographic differentials CDW is committed to being an AI-fluent organization We’re looking for people who bring curiosity, a learner’s mindset, and a willingness to engage with ever-evolving technology and tools. We value adopting AI as a partner, openness to experimentation, and a shared interest in learning together on AI. Our goal is to create a culture where AI enhances—not replaces—human creativity and decision-making. You don’t need to be an expert today; what matters is your readiness to explore, adapt, and grow with us as we integrate AI responsibly and effectively into our work. Additionally, CDW is committed to fostering an equitable, transparent, and respectful hiring process for all applicants. During our application process, our goal is to understand your experience, strengths, skills, and qualifications. As an AI forward company, we see AI not just as a tool, but as a catalyst for new ways of thinking, creating, and communicating. We encourage candidates to embrace an AI mindset, one that’s curious, adaptive, and ready to explore what’s possible. We welcome thoughtful use of AI to expand your perspective and elevate how you share your story, while ensuring your application remains rooted in your own background, judgment, and voice. About Us CDW is a Fortune 500 technology solutions provider that helps businesses, government, education, and healthcare organizations achieve what’s possible through technology. What makes CDW different isn’t just what we do—it’s how we do it. At CDW we act as one—building trust, speaking candidly, and working together to achieve more. We play to win—focusing on what matters most and delivering for our customers. And we think forward—staying curious, moving fast, and continuously learning. We believe meaningful work happens when people feel supported, heard, and empowered to contribute. That’s why we think of ourselves as coworkers, not just employees—working together to solve complex challenges and deliver real impact for our customers and communities. As a full‑stack, full‑lifecycle technology partner, CDW brings deep expertise, strong relationships, and broad industry knowledge to help turn ideas into outcomes. When you join CDW, you become part of a collaborative environment where your work matters, your growth is supported, and your contributions help shape what’s next. Together, we deliver the full promise of what technology can do. Together, we Make Amazing Happen. CDW is an equal opportunity employer. All qualified applicants will receive consideration for employment without regards to race, color, religion, sex, sexual orientation, gender identity, national origin, disability status, protected veteran status or any other basis prohibited by state and local law.

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