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Principal Strategist - Healthcare

CDW · IL · Remote available · $157,500–$213,500 a year · Full time

Posted Sep 22, 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 you shaped the thinking of a customer executive, like a CIO or CMIO, about their technology strategy.

What they are checking: Whether they can operate as a peer to healthcare leadership, which is the core of a strategist role.

Tell me about a partner technology you brought into a solution to solve a real customer problem.

What they are checking: Whether they can coordinate partners around actual needs, not just add products to a deal.

How do you stay current on healthcare and technology trends, and how do you share what you learn with sellers?

What they are checking: Whether their thought leadership reaches the field team and turns into better customer conversations.

Tell me about a presentation to customer leadership that did not go as planned. What did you do?

What they are checking: Their composure and ability to adjust when an executive audience pushes back.

What would you do

A hospital wants to talk about AI, but their data and infrastructure are not ready. How do you advise them?

What they are checking: Whether they give honest advice that builds trust, even if it slows a near-term sale.

A seller wants you in a meeting to help close a product deal, but the customer needs a bigger conversation. How do you handle it?

What they are checking: How they balance supporting short-term sales with their strategic advisory role.

About the work

What are the biggest technology challenges facing health systems right now, and which ones do you think are most underestimated?

What they are checking: Whether they have current, specific industry insight rather than general healthcare IT talking points.

How would you decide whether a new offering in healthcare is worth CDW building?

What they are checking: Their ability to evaluate market potential, the problem solved and fit with CDW's existing solutions.

How do HIPAA and patient safety concerns change the way you position a technology solution?

What they are checking: Whether they understand the regulatory and clinical stakes that shape healthcare buying decisions.

How would you measure whether your work as a strategist is accelerating growth in the healthcare segment?

What they are checking: Whether they can connect advisory work to outcomes the business cares about.

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The full job description

As published by CDW.

Job Summary The Strategist role is responsible for helping to understand customer business challenges and objectives that can benefit from technology and drive solutions within CDW segments by partnering with key internal and external stakeholders, and technology partners to understand current and emerging technology initiatives, ultimately accelerating growth within the segment and positioning CDW as a preferred partner within the market. This role is primarily responsible for advising CDW on new offerings to address industry challenges and opportunities. What you will do • Be part of the overall strategist organization to be thought leaders in leveraging technology to positively impact the segment • Interact with customer leadership to help shape future thinking • Achieve goals, and improve their organizations’ posture • Present and demonstrate strategy and solutions and specific partner technologies to customers and CDW • Stay current on trends and technology developments • Participate in the development of CDW’s solution sets to solve customer problems within the industry • Coordinate partner participation in specific solutions addressing real needs outside of traditional technology infrastructure • Understand and evaluate new technology approaches and solutions to understand the value, problem addressed, market potential, and fit into the CDW strategic solutions • Work with other areas within CDW to develop the solution package to include services, logistics and other capabilities, as appropriate, for solutions selected as CDW offerings • Determine the accounts within target markets • Qualify and scope solutions opportunities within accounts • Determine the market (s) to address • Develop relationships with executives at organizations and partners to further align CDW to the evolving needs of our customers • Work closely with multiple stakeholders at the customer to influence the final requirements of the target opportunity, including executives, program leads, project leads, and technical experts • Collaborate with sales team to act as subject matter expert for customer visits and presentations, customer conference calls and webinars, as well as participate in all aspects of large solutions • Articulates value proposition to sellers, partners and customers. • Attends customer onsite meetings, business reviews, and industry days, as needed. • Represents company at external business networking opportunities, conferences, and events. • Training CDW sellers and sales teams on trends and solutions and mentor CDW sellers on messaging to their customers. What we expect of you Minimum basic requirements • Strong customer facing skills with a history of building solid relationships with leaders. • Deep understanding of the customer’s business with credibility as a strong career leader in the market • Experience in a role requiring proven leadership, facilitation, critical thinking and problem-solving skills as well as a strong customer service. • Strong understanding of the market. • 10 years prior experience working within the specific industry. • Proven track record of success in navigating procurement departments for additional opportunities. • Demonstrated understanding of technology trends, technology architecture and roadmaps. • Experience in a leadership role in the implementation of technology solutions involving integrations, configuration, troubleshooting, training, adoption and support. • Proven ability to influence across all functions of an organization. • Strong strategic planning ability. • Effective communication skills both oral and written using a variety of styles and techniques appropriate to the audience • Excellent presentation skills • Demonstrated collaboration behavior with excellent facilitation and negotiation skills. • Strong problem-solving skills with demonstrated ability to find solutions while working independently. • Must be able to communicate effectively and in a constructive manner with management, peers, and coworkers. • Demonstrated ability to manage multiple priorities/projects, meet deadlines, facilitate change, and delegate responsibility. • Travel required as needed Preferred Qualifications Preferred skills, experience, and qualities needed • Bachelor’s degree • Experience as a CIO, CTO, IT Vice President or IT Senior Leader • Experience leading IT strategy and operations within the specific industry • 10 or more years’ experience in assessing business drivers and translating them into qualifiable, quantifiable and tactical solutions • Understanding technologies and the challenges of implementing new technologies into a highly regulated and complex technology ecosystem. • Industry related certifications ie. CISSP, CSSP, CISM, CRISC, GCIH • Working knowledge and understanding of standard industry regulations i.e. FERPA, HIPAA, GDPR, CPRA Pay range: $ 157,500 - $213,500 depending on experience and skill set Annual bonus target of 43% 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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