AI Transformation Lead

AI Transformation Lead

United States · Full-Time · Customer Enablement

Why Raspberry AI

Raspberry AI is building the agentic platform transforming how fashion and retail is created and brought to market. Raspberry brings AI into the center of their process — connecting design, product development, merchandising, marketing, ecommerce, and wholesale teams in one platform.

Our customers use Raspberry to move from an idea to production-ready designs, assortments, campaigns, ecommerce imagery, and sales materials in a fraction of the time. Today, some of the world's leading fashion brands and retailers — including SKIMS, Fabletics, Under Armour, Oscar de la Renta, Walmart, rag & bone, Kate Spade, Savage x Fenty and more are using Raspberry to rethink how their teams work.

We've raised $29M from a16z, Khosla Ventures, Greycroft, and leaders across the fashion industry. This is an opportunity to help the world's leading fashion and retail brands rethink how product creation happens in the age of generative AI.

About the Role

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 — becoming an expert in Raspberry's platform capabilities and in how our most advanced customers integrate AI into day-to-day work.

You'll translate successful usage patterns into scalable playbooks, implementation strategies, and enablement frameworks; advise customers on the organizational changes needed to implement AI workflows across large, cross-functional teams; and drive transformation initiatives at enterprise retail organizations ranging from hundreds to thousands of users. You'll lead strategic workshops, product trainings, workflow audits, and executive business reviews — acting as a trusted advisor to customer leadership — while working cross-functionally with Product, Engineering, Customer Success, and Sales to feed recurring workflow gaps and insights back into roadmap prioritization.

Who you are

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

Strong interest in generative AI tools and creative workflows (Midjourney, Firefly, ComfyUI, Krea, Runway, or similar)

Experience driving operational change management or technology transformation within large organizations

Exceptional communication and storytelling skills — able to influence both executives and hands-on creative teams

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

Strong documentation and enablement skills, with the ability to build scalable frameworks and playbooks

Comfortable navigating ambiguity in fast-moving, high-growth environments

How we work

Be an owner: We take responsibility for outcomes, not just tasks. We don't wait for permission — we step up, move fast, and hold ourselves accountable to results.

Bias to solution: We go beyond identifying problems to actively unblocking ourselves and others.

Customer obsession: Everything we build starts with the customer. We listen deeply, move quickly, and obsess over delivering tools that make their work faster and more creative.

Lowest level of detail: We're not afraid to get in the weeds. Great work comes from people who notice what others miss and ask deeper questions.

1% better every day: Progress compounds. We stay curious, ask for feedback, and look for the small improvements that make tomorrow better than today.

AI first: We use AI across the entire company — from product to growth to operations — to move faster and produce higher-quality work.

What we offer

Innovative culture: a generational opportunity to define the role of AI in one of the world's largest industries

Growth paths: opportunities to drive impact well beyond your immediate role as the company scales

Learning & development: annual discretionary stipend for professional development

Annual company offsite that brings the whole team together

Competitive salary and equity options

Comprehensive benefits package including health, dental, and vision insurance