AI Transformation Lead

About the Role

Raspberry AI is looking for an AI Transformation Lead to help the world’s leading fashion and retail brands rethink how product creation happens in the age of generative AI. This is a highly strategic, customer-facing role focused on driving large-scale AI workflow adoption across enterprise organizations. You’ll partner closely with design, merchandising, product development, and executive stakeholders to identify high-impact workflows, operationalize best practices, and guide teams through AI-enabled transformation. You’ll become an expert in Raspberry AI’s platform capabilities and deeply understand how our most advanced customers are integrating AI into their day-to-day workflows. From there, you’ll translate successful usage patterns into scalable playbooks, enablement frameworks, and operational recommendations that can be applied across the broader customer base. This role sits at the intersection of AI strategy, workflow design, product enablement, and enterprise transformation. It’s ideal for someone who understands both the creative and operational realities of large retail organizations and can influence adoption at scale.

Responsibilities

• Partner closely with enterprise customers to understand how teams adopt and operationalize AI across creative and production workflows.

• Identify high-performing customer workflows and translate them into scalable playbooks, implementation strategies, and best practices for broader customer adoption.

• Advise customers on organizational and operational changes required to successfully implement AI workflows across large teams and cross-functional organizations.

• Drive AI transformation initiatives across enterprise retail organizations ranging from hundreds to thousands of users.

• Work cross-functionally with Product, Engineering, Customer Success, and Sales teams to influence product direction and improve customer outcomes.

• Create clear documentation, enablement materials, workflow frameworks, and executive-ready recommendations for internal and external stakeholders.

• Lead strategic customer workshops, product trainings, workflow audits, and executive business reviews.

• Act as a trusted advisor to customer leadership teams, helping them understand how generative AI can improve speed, efficiency, creativity, and organizational alignment.

• Surface recurring workflow gaps, customer pain points, and operational insights to influence roadmap prioritization and product strategy.

• Stay at the forefront of AI-native creative workflows and emerging industry trends across fashion, retail, and digital product creation.

Qualifications

• 10+ years of experience in fashion, retail, enterprise SaaS, AI workflow consulting, product operations, digital transformation, or creative systems implementation.

• Deep understanding of retail, fashion, or product development workflows across design, merchandising, sourcing, and production organizations.

• Strong interest in generative AI tools and creative workflows with platforms such as Midjourney, Firefly, ComfyUI, Krea, Runway, or similar systems.

• Experience driving operational change management or technology transformation initiatives within large organizations.

• Exceptional communication and storytelling skills — able to influence both executive stakeholders and hands-on creative teams.

• Proven ability to translate complex product capabilities into practical operational workflows and measurable business outcomes.

• Highly strategic and systems-oriented thinker who can connect individual workflows to broader organizational transformation.

• Strong documentation and enablement skills with the ability to create scalable frameworks, playbooks, and customer education materials.

• Comfortable navigating ambiguity and operating in fast-moving, high-growth environments.

• Strong cross-functional instincts with experience partnering across Product, Engineering, Customer Success, and GTM teams.

• Passion for AI-native workflows and excitement about shaping the future of fashion and retail technology.

• Self-starter mentality with a high level of ownership, accountability, and operational rigor.