Executive Enterprise Strategist — IT Transformation & AI

CDW; Illinois; On-site; USD 151,000 - 212,000; Full time

Job summary

CDW is seeking a Principal Enterprise Strategist to lead Pre-Sales - Services Engagement, translating business goals into technology strategies and actionable roadmaps. You will guide enterprise IT transformations, engage executive clients, and drive innovation across CDW’s technology portfolio.

You will influence senior stakeholders, shape multi-practice solutions, and publish strategic IP while collaborating with R&D, delivery teams, and various organizations.

Qualifications

• Bachelor’s degree required and 10+ years of experience OR 14+ years of work experience required
• Experience designing multi-practice solutions for complex customer environments
• Strong understanding of CDW’s portfolio including Cloud, applications, data, security, modern infrastructure, DevOps, SaaS technologies, and AI
• Proven ability to influence business and IT stakeholders at the executive level
• Demonstrated success building and delivering enterprise technology roadmaps and digital transformation strategies
• Certifications across multiple disciplines (AWS Solutions Architect, Azure Architect Expert) is a plus
• Background in vertical-specific architecture (financial services) is a plus
• Strategic mindset with ability to translate vision into executable strategies is a plus
• Executive presence with strong communication skills is a plus
• Cross-domain expertise across integrated technology solutions is a plus
• Innovation and agility in fast-paced environments is a plus
• Collaborative leadership across sales, engineering, and delivery teams is a plus
• Outcome-driven focus on measurable business impact is a plus

Responsibilities

• Provide strategic advisory consulting to clients, translating business objectives into technology strategies and actionable roadmaps.
• Guide long-term IT transformation, ensuring scalability, interoperability, and alignment to business outcomes.
• Identify opportunities early by spotting emerging technical trends.
• Conduct executive-level workshops and multi-practice technology visioning sessions.
• Lead financial impact modeling to support new products, services, and partner-adjacent initiatives.
• Collaborate across Digital Infrastructure, Digital Velocity, Managed Services, and Global Security Strategy Office (GSSO).
• Support solution scaling and transition planning in partnership with R&D and delivery teams.
• Act as a segment-wide evangelist for transformational technologies (cloud-native platforms, automation, AI/ML).
• Publish white papers, build reusable IP (frameworks, templates), and deliver external presentations.
• Provide non-billable advisory oversight during delivery of multi-practice solutions to ensure architectural integrity and alignment with intended outcomes.

Skills

Strategic advisory

Executive influence

Roadmap design

Digital transformation

Cross-domain expertise

Leadership collaboration

AI/ML awareness

Innovation mindset

Communication skills

Stakeholder management

Education

Bachelor’s degree

Tools

AWS Solutions Architect

Azure Architect Expert

Job description

CDW is seeking a Principal Enterprise Strategist to lead Pre-Sales - Services Engagement, translating business goals into technology strategies and actionable roadmaps. You will guide enterprise IT transformations, engage executive clients, and drive innovation across CDW’s technology portfolio.

You will influence senior stakeholders, shape multi-practice solutions, and publish strategic IP while collaborating with R&D, delivery teams, and various organizations.