Whereoware, Inc Careers

The Digital Strategy Principal is a senior strategic leader responsible for identifying, validating, and driving digital growth opportunities through data, customer experience, and innovation. This role transforms business intent into actionable digital strategies that deliver measurable enterprise value.

Working across large, complex organizations, the Digital Strategy Principal partners closely with Client Strategists, Experience Designers, and business leaders to align enterprise priorities across Sales, Marketing, and Service. The ideal candidate combines strategic acumen with hands-on execution, leading workshops, defining outcomes, developing journey maps, and creating actionable roadmaps that translate data and insights into business impact.

This is a highly visible, client-facing role ideal for a strategist experienced in navigating global enterprises, managing senior stakeholders, and driving transformation at scale.

Key Responsibilities

Go-to-Market & Acquisition

• 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.

Solutions & Delivery

• 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.

Client Growth & Retention

• 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.

Qualifications

• 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.
• Certification or formal training in Design Thinking or human-centered design (LUMA Institute or similar preferred).
• 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.

Reporting & Collaboration

• Reports to: Chief Strategy Officer (CSO)
• Works closely with: Client Strategists, Experience Designers, Data Analysts, and Digital Delivery Leaders
• Partners with: Executive stakeholders across Sales, Marketing, and Service to align digital transformation goals with measurable outcomes

Whereoware, Inc is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, or protected veteran status, or any other protected characteristic, and will not be discriminated against on the basis of disability.