[Remote] Digital Strategy Principal

Note: The job is a remote job and is open to candidates in USA. Whereoware is a company focused on driving digital growth opportunities through data and innovation. The Digital Strategy Principal is responsible for transforming business intent into actionable digital strategies while collaborating with various stakeholders to align enterprise priorities across Sales, Marketing, and Service.

Responsibilities

• Identify and validate digital growth opportunities using data, insights, and innovation frameworks
• Define and evolve digital innovation narratives and methodologies to support market differentiation and brand positioning
• Shape early-stage digital strategy and roadmaps for large-scale pursuits
• Co-lead executive presentations and proposals, articulating transformation value and ROI
• Collaborate with Sales to develop compelling business cases for complex client engagements
• Define digital strategic direction determining how to execute, optimize, and prioritize to achieve measurable impact
• Own and evolve strategic delivery frameworks, including transformation roadmaps, CX models, and measurement systems
• Ensure digital initiatives align with enterprise KPIs and drive cross-functional alignment across Sales, Marketing, and Service
• Guide prioritization of digital programs and identify risks that could impact delivery or client success
• Lead change management and enablement efforts to support adoption of digital strategies across enterprise environments
• Optimize planning cycles and execution frameworks using performance insights to ensure strategy translates into measurable outcomes
• Serve as a trusted advisor to executive stakeholders, linking digital performance to long-term transformation
• Co-lead strategic planning and pipeline prioritization with Client Strategists and senior stakeholders
• Monitor digital maturity and CX performance, identifying expansion opportunities through measurable results
• Lead quarterly business reviews and strategic alignment sessions to ensure continued value delivery and growth
• Facilitate enterprise workshops using Design Thinking and human-centered design (LUMA certification preferred)
• Educate clients and internal teams on digital strategy frameworks, CX models, and measurement best practices
• Champion a culture of experimentation, data-driven decision-making, and continuous improvement

Skills

• 10+ years of experience in digital strategy, transformation, or CX innovation for enterprise-level clients (Fortune 1000 or comparable scale)
• Proven ability to navigate complex stakeholder ecosystems and lead multi-functional collaboration across large organizations
• Hands-on experience facilitating executive-level workshops, defining business outcomes, and developing strategic roadmaps that drive measurable results
• Deep understanding of customer experience strategy across Sales, Service, and Marketing ecosystems
• Demonstrated success connecting data, digital execution, and business transformation
• Strong communication, storytelling, and relationship management skills with C-suite and senior executives
• Experience in change management, risk mitigation, and performance optimization within enterprise-scale initiatives
• Certification or formal training in Design Thinking or human-centered design (LUMA Institute or similar preferred)

Company Overview

• Whereoware is a digital agency that specializes in the development of personalized websites and mobile applications. It was founded in 1999, and is headquartered in Chantilly, Virginia, USA, with a workforce of 51-200 employees. Its website is http://www.whereoware.com.