# Willowood — Chief Digital Transformation Officer

- Generated: 2026-08-28 12:25:36 PM EDT
- Original/canonical posting: https://www.linkedin.com/jobs/view/4458981326/
- Posted: 35 minutes ago at capture time
- Applicants: Be among the first 25 applicants
- Work model/location: United States; remote/hybrid/on-site arrangement is not disclosed or verifiable
- Employment type: Part-time
- Compensation: Not disclosed; Chief title would otherwise qualify
- Travel: Not disclosed
- Positioning track: Executive leader
- Fit outcome: FAIL — 67%

## Direct-match strengths

Enterprise AI, data, cloud, automation, ERP modernization, quantified process improvement, workforce enablement, and change leadership are strong.

## Hard or material gaps

Hard work-model failure: the listing supplies only United States and no role-specific remote badge or text, while Keith requires U.S. remote or Massachusetts-based work. Board-level global portfolio ownership, omnichannel digital-customer experience, and CFO-grade benefits-realization governance are also only partially supported.

## Weighted evidence map

1. Enterprise transformation strategy and governance — 2/3: Direct enterprise roadmaps and executive reporting; Board-level portfolio ownership is less explicit.
2. Digital operating model and process redesign — 2/3: Direct multi-division data/process transformation; global operating-model ownership is less explicit.
3. AI, automation, cloud, and data transformation — 3/3: Direct quantified production evidence.
4. ERP and legacy-platform modernization — 3/3: Direct integration of 11 ERP environments into an AWS data platform.
5. Digital customer experience and omnichannel ownership — 1/3: Adjacent product and contact-center work, not enterprise omnichannel ownership.
6. Global portfolio, budgets, and benefits realization — 1/3: Project and budget evidence is direct; global transformation-portfolio ownership is not.
7. Workforce adoption and reskilling — 3/3: Direct team upskilling and global AWS enablement.
8. Verified compatible work model — 0/3: No remote evidence and no Massachusetts location.

## Full normalized job description

Chief Digital Transformation Officer (CDTO)
Position Summary
The Chief Digital Transformation Officer (CDTO) is the senior executive responsible for leading the organization’s enterprise-wide digital transformation strategy and execution. The role integrates digital strategy, AI, intelligent automation, technology modernization, data transformation, business-process redesign, and digital customer experience to create measurable enterprise value.
The CDTO acts as the bridge between business strategy and technology execution, ensuring digital investments improve revenue growth, productivity, operational efficiency, scalability, customer experience, and competitive advantage.
Key Responsibilities
1. Enterprise Digital Transformation Strategy
Develop and execute the enterprise-wide digital transformation strategy.
Establish a multi-year digital transformation roadmap.
Translate CEO and Board priorities into digital initiatives.
Prioritize investments according to strategic value, ROI, risk, and scalability.
Establish transformation KPIs, milestones, budgets, and governance.
2. Digital Operating Model
Design and implement technology-enabled operating models.
Redesign organizational workflows, processes, governance, and decision rights.
Standardize digital capabilities across business units and regions.
Build scalable, digitally enabled enterprise capabilities.
3. AI & Intelligent Automation
Lead enterprise adoption of generative AI, machine learning, RPA, and intelligent automation.
Identify high-value AI use cases across Finance, Marketing, Sales, Operations, Supply Chain, and Customer Service.
Develop AI-enabled workflows and operating models.
Establish AI governance, risk controls, and adoption frameworks.
Measure AI-driven productivity and financial benefits.
4. Technology Modernization
Lead modernization of legacy systems and technology platforms.
Partner with CIO and CTO organizations on cloud, ERP, CRM, data, and enterprise-platform transformation.
Evaluate emerging technologies and their business applications.
Ensure technology investments generate measurable business outcomes.
5. Business Process Transformation
Identify inefficient, manual, and fragmented processes.
Lead enterprise process redesign and automation.
Reduce cycle times, operating costs, and organizational complexity.
Apply Lean, Agile, Six Sigma, and process-engineering methodologies.
Establish continuous digital-improvement programs.
6. Data & Analytics Transformation
Develop enterprise data and analytics capabilities.
Improve data quality, governance, accessibility, and integration.
Establish real-time executive dashboards.
Apply predictive analytics and AI to strategic decision-making.
Integrate financial, operational, customer, and commercial data.
7. Digital Customer Experience
Lead transformation of digital customer journeys.
Modernize websites, portals, mobile applications, and self-service channels.
Develop omnichannel and personalized customer experiences.
Partner with the CMO and Chief Customer Officer.
Use AI and automation to improve engagement, retention, and customer lifetime value.
8. Digital Product & Platform Strategy
Partner with Product, Engineering, Marketing, and Commercial leadership.
Identify opportunities for digital products and services.
Develop digital-platform and ecosystem strategies.
Support digital commercialization and new business models.
Evaluate technology-driven opportunities for competitive differentiation.
9. Transformation Portfolio Governance
Oversee the enterprise portfolio of digital-transformation initiatives.
Establish investment-review and transformation-governance processes.
Monitor budgets, milestones, risks, dependencies, and benefits realization.
Coordinate major cross-functional and multinational programs.
Maintain executive-level visibility into transformation performance.
10. Financial Value Creation
Partner with the CFO on digital-transformation business cases.
Quantify ROI, productivity gains, cost savings, and revenue opportunities.
Establish benefits-realization frameworks.
Optimize digital investment allocation.
Track actual versus expected transformation value.
11. Organizational Transformation
Lead workforce and organizational changes associated with digital modernization.
Partner with HR on reskilling and digital capability development.
Develop adoption strategies for new technologies and processes.
Build a culture of digital innovation and continuous improvement.
12. Executive Leadership
Lead the global digital-transformation organization.
Develop senior digital and transformation talent.
Present digital strategy, progress, risks, investment requirements, and outcomes to the CEO and Board.
Establish enterprise accountability for digital transformation.
Qualifications
Bachelor’s degree in Computer Science, Information Systems, Engineering, Business, Finance, or related field
MBA, MS, or other advanced degree preferred
18–25+ years of experience in digital transformation, technology, strategy, consulting, operations, or business leadership
10+ years of senior executive leadership
Proven experience leading enterprise-scale digital transformation
Strong knowledge of AI, automation, cloud, enterprise systems, data, analytics, and digital operating models
Strong financial, strategic, and organizational leadership capabilities
Core Competencies
Enterprise Digital Transformation
Digital Strategy
AI & Intelligent Automation
Technology Modernization
Digital Operating Model
Business Process Reengineering
Data & Analytics
Digital Customer Experience
Digital Product Strategy
Change Management
Transformation Governance
Enterprise Architecture
Value Realization
Strategic Execution

## Artifact metadata

- Resume and cover letter: Not generated under the fit gate.
- LinkedIn note: Not generated for a FAIL role.
- Google Drive used: No