Director of AI, Transformation & Strategic Initiatives

Windsor is a dynamic fashion retailer driven by an entrepreneurial spirit. Our culture is fast-paced, collaborative, and rooted in continuous learning. 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. By combining creativity, technology, and operational excellence, we are building for the future while staying true to our values. As a newly created role, this position offers the opportunity to build the foundation for Windsor’s AI transformation and create a lasting legacy for the brand.

Job Summary

The Director of 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 will be business savvy and combine visionary thinking with a player-coach 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.
• Lead cross-functional teams from discovery through adoption of AI initiatives.
• Establish governance and best practices for responsible AI usage.
• Work with IT to ensure Windsor has the data and 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:

• At least 5 years of experience in consulting, strategy, business operations 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 AI capabilities to support business improvement.
• Strong organizational skills and attention to detail.
• Passion for learning and applying AI technologies to real business problems.

Preferred:

• Management consulting experience.
• Experience using AI to support business improvements.
• Retail, ecommerce, consumer, or fashion industry experience is 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.
• Build and prioritize a portfolio of high-impact AI initiatives.
• Manage cost of AI usage across the business.
• Apply best practices for AI across our business channels.

Within the first twelve months, this leader will:

• Start to deliver measurable productivity and efficiency.
• Increase organizational adoption and understanding of AI tools.
• Create measurable value through cost savings, productivity and revenue growth.
• Become a trusted advisor to executives and business leaders across the organization.

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