VP of AI, Transformation & Strategic Initiatives

Windsor is a dynamic, customer-focused fashion retailer driven by an entrepreneurial spirit, a passion for innovation, and a commitment to delivering exceptional experiences. Our culture is fast-paced, collaborative, and rooted in continuous learning, where team members are empowered to challenge the status quo, move with agility, and make meaningful contributions. As we continue to grow and evolve, Windsor has embraced transformation across every aspect of the business—from enhancing the customer journey and strengthening our digital capabilities to modernizing operations and leveraging data-driven decision-making. We view change as an opportunity to innovate, continuously improving how we serve our customers, support our teams, and operate our business. By combining creativity, technology, and operational excellence, we are building a future-ready organization positioned for long-term success while staying true to our values and the unique culture that defines Windsor.

 

Job Summary

The Vice President, AI Transformation & Strategic Initiatives will report to our CEO & President and serve as a trusted advisor to our Executive Leadership Team, leading Windsor's company-wide AI transformation journey. This highly visible role will be instrumental in shaping the future of the business by reducing costs, increasing sales, enhancing customer experience, and strengthening decision-making across the organization. They will work with leaders across all functions—including Marketing, Creative, Merchandising, Planning, Stores, Ecommerce, Finance, Operations, Customer Service, Human Resources, and Technology—to evaluate opportunities, build business cases, align stakeholders, and help drive implementation. The ideal candidate combines visionary thinking with a hands-on, player-coach leadership style. They are intellectually curious, have strong business acumen, exceptional communication skills, and a passion for continuous improvement.  Most importantly, this leader will embody and champion Windsor's values while helping shape the next chapter of growth through the power of AI and strategic innovation.

 

Essential Job Functions & Responsibilities:

• Develop Windsor’s AI strategy in alignment with the business strategy 
• Identify and prioritize AI opportunities and use cases across all areas of the business.
• Partner with executives and department leaders to understand business challenges and uncover opportunities for automation, optimization, and innovation.
• Evaluate and prioritize potential initiatives based on ROI opportunity, financial impact, operational benefits, implementation complexity, and organizational readiness.
• Facilitate executive updates, steering committees, and decision-making processes.
• Establish success metrics and measurement frameworks. Track project outcomes and ensure expected benefits are realized.
• Lead cross-functional teams through discovery, planning, testing, implementation, and adoption of our AI initiatives.
• Establish governance and best practices for responsible AI usage.
• Work closely with IT to make sure Windsor has the data capability and technology/systems to enable AI effectiveness
• Stay current on emerging AI technologies, tools, and best practices.
• Lead education initiatives to raise AI fluency at Windsor

Key Qualifications & Requirements:

• 5-10 years of professional experience in consulting, strategy, business operations, transformation, technology, or a related field.
• Strong analytical and financial modeling skills.
• Proven ability to manage complex cross-functional initiatives.
• Outstanding communication, presentation, and stakeholder management abilities.
• Demonstrated experience influencing senior leadership.
• Demonstrated capability to develop AI GPTs. Skills, and / or Agents to support business improvement. 
• Strong organizational skills and attention to detail.
• Ability to balance strategic thinking with hands-on execution.
• Passion for learning and applying AI technologies to real business problems

Preferred:

• Management consulting experience (McKinsey, Bain, BCG, Accenture, Deloitte, EY-Parthenon, LEK, Oliver Wyman, or similar).
• Experience leading digital transformation or AI-related initiatives.
• Retail, ecommerce, consumer, or fashion industry experience a plus.
• Familiarity with AI platforms, workflow automation tools, analytics platforms, and enterprise software ecosystems.

What Success Looks Like

Within the first six months this leader will:

• Understand how the business operates and what drives success  
• Develop firm-wide AI strategy, governance framework, and LLM tool management.
• Establish a company-wide framework for evaluating AI opportunities.
• Build a prioritized portfolio of high-impact AI initiatives.
• In addition to developing a framework to measure benefits, understand the cost implications of AI usage across the business. 
• To the degree practical, understand best practices for AI across the retailing, Ecom, and fashion industries and maintain a process for keeping this current. 

Within the first twelve months, this leader will:

• Start to deliver measurable productivity and efficiency gains across multiple departments
• Increase organizational adoption and understanding of AI tools. Not first six months?
• Create measurable financial value through cost savings, productivity improvements, and revenue growth initiatives.
• Become a trusted advisor to executives and business leaders across the organization.

Who Will Thrive at Windsor

This role is ideal for someone who:

• Is energized by building and creating rather than maintaining the status quo.
• Can influence without formal authority.
• Thinks like an owner and acts with urgency.
• Is comfortable working in a fast-paced environment with evolving priorities.
• Enjoys being both strategic and hands-on.
• Embodies Windsor's culture of continuous improvement, accountability, teamwork, and value creation.

Physical/Environmental Demands and Overtime & Availability: Work is performed in an office environment and requires the ability to operate standard office equipment and keyboards. Must have the ability to walk short distances. Sedentary work. Exerting up to 10 pounds of force occasionally and/or a small amount of force frequently or constantly to lift, carry, push, pull or otherwise move objects. Repetitive motion. Adequate movements (motions) of the wrists, hands, and/or fingers. Team members are required to have close visual acuity to perform activities such as: preparing and analyzing data and figures; transcribing; viewing a computer terminal; extensive reading.

*Job descriptions are merely a summary of the position. Duties and responsibilities are subject to change and may include any other that management finds necessary to successfully maintain business operations.

WINDSOR EQUAL OPPORTUNITY EMPLOYER