Mid Level Enterprise Customer Success Jobs

INTRODUCTION

Raspberry AI is a generative AI design platform built for fashion brands and retailers. We help design, merchandising, and product development teams move faster — from concept to market-ready assets — using industry-leading AI. Some of the world's top fashion brands rely on Raspberry AI to streamline their workflows and accelerate product development. We closed $24 million in Series A from a16z, plus $5 million seed rounds from Khosla Ventures and Greycroft Ventures. Other investors include REVOLVE and Reformation founders, and the President of Saks Fifth Avenue.

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're solutions-oriented at heart. 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: We bring the whole team together once a year.

THE ROLE

Raspberry AI is looking for an Enterprise Customer Success Manager to own and grow our most important enterprise relationships — $1B+ retailers and global consumer brands navigating a once-in-a-generation shift in how creative work gets done. You'll be the trusted partner who turns early AI adoption into deep, durable value: guiding design teams and leadership through meaningful workflow transformation, building the business case at the executive level, and expanding Raspberry's footprint in the accounts that define our category. This is a high-visibility, high-ownership role. You'll sit at the intersection of customer success, change management, and creative industry expertise — partnering with VP- and C-suite stakeholders to drive measurable outcomes from day one.

- Own a portfolio of strategic enterprise accounts ($1B+ retailers and global consumer brands), serving as the primary relationship owner from post-sale through expansion and renewal.
- Build and execute account plans with clear adoption milestones, executive engagement cadences, and measurable ROI frameworks.
- Drive AI adoption across complex, matrixed organizations — navigating multiple business units, stakeholder layers, and change management challenges with confidence.
- Lead executive business reviews (QBRs) with VP- and C-suite audiences, translating usage data and workflow metrics into compelling business narratives.
- Identify and close expansion opportunities in close partnership with the Account Executive team.
- Proactively monitor account health, surface churn risks early, and own resolution with urgency.
- Become a trusted domain expert on AI-assisted creative workflows — advising customers on how to embed Raspberry into design, merchandising, and go-to-market processes.
- Partner cross-functionally with Product, Engineering, and Marketing to relay customer insights that shape the roadmap.
- Represent Raspberry at customer sites and industry events; periodic travel required.

WHAT WE'RE LOOKING FOR

Must-Haves

- 3-5+ years in Customer Success, Strategic Account Management, or a related enterprise-facing role at a SaaS or AI company.
- Demonstrated track record of growing and retaining $1B+ retailer or global consumer brand accounts — you've worked directly with VP- and C-suite stakeholders and understand how large brands make decisions.
- Proven experience driving AI or enterprise software adoption inside complex, matrix organizations — you know how to build champions, navigate change resistance, and move large institutions forward.
- Strong commercial instincts: comfortable owning retention and expansion targets, able to articulate ROI in the language of a CFO and a Creative Director alike.
- Executive-level communication skills — polished, concise, and credible in any room.
- New York City-based with the ability to be in our Dumbo, Brooklyn office one day per week.

Bonus Points

- Background in fashion, apparel, luxury, or the broader creative/design industry — you've worked inside or alongside design teams and understand their tools, pressures, and workflows.
- Experience with generative AI tools, creative technology platforms, or AI workflow enablement.
- Familiarity with PLM, DAM, or retail tech ecosystems (e.g. Centric, Bynder, Contentful).
- Experience working with global brand portfolios or multi-brand holding companies.

BENEFITS

- Competitive salary and equity options.
- Unlimited PTO.
- Comprehensive benefits package including health, dental, and vision insurance.
- Opportunity to work on cutting-edge AI technology with a high-impact team.
- Fully remote with a supportive company culture.
- Be part of a rapidly growing company with significant growth potential.

COMPENSATION

- The base salary range for this role is $150,000 – $160,000 annually, with a 25% variable component — bringing total on-target earnings to around $200K for the right candidate.

Raspberry AI is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.