Shape the future of design

Raspberry AI

Raspberry AI is a leading provider of industry-defining AI design software for fashion brands and retailers. Our software empowers brands to rapidly understand consumer demand and create unique designs within minutes. Leveraging cutting-edge AI analytics and generative AI capabilities, we help fashion brands revolutionize their design and merchandising processes.

We are a Series A startup, backed by top-tier venture capital firms such as Andreessen Horowitz, Khosla Ventures, MVP and Greycroft.

About the Role

We’re hiring Strategic Account Executives in New York to lead full-cycle, enterprise-level deals across fashion, travel, home goods, lifestyle brands and other retail brands.

The right AE will combine enterprise rigor, resourceful outbound creativity, and executive polish—driving annual and multi-year contracts through multi-threaded relationships.

This is a scaling role for reps who’ve already mastered structured selling and want to build repeatability in a high-growth AI startup.

You’ll be part of the GTM team driving Raspberry AI’s next stage of growth—helping define what elite, value-driven enterprise selling looks like in the AI era. This is a high-ownership role for operators who thrive in ambiguity, move fast, and turn every touchpoint into momentum.

Responsibilities

• Own the full sales cycle: prospect → qualify → demo → negotiate → close → expand.
• Develop multi-threaded relationships across Marketing, Innovation, IT, and Procurement.
• Craft ROI-driven executive narratives and business cases.
• Run 3–6 month cycles with focus on annual contracts, expansion, and retention.
• Build creative pipeline through outbound, phone, events, and social proximity—not just sequences.
• Collaborate with Product, CS, and Marketing on account strategy.

Requirements

• 8–10 years of B2B SaaS closing experience, ideally $250K–$750K+ ACV.
• Proven success in enterprise / upper-mid market deals with multi-stakeholder complexity.
• Demonstrated ability to own negotiations end-to-end, from commercial structure through contract execution. Comfortable navigating legal, procurement, and compliance processes directly.
• Experience pricing and packaging complex, usage-based or credit-consumption models, not just seat-based licenses.
• Deep experience with outbound prospecting and self-sourced pipeline creation.
• Strong negotiation skills, MEDDICC fluency, and forecasting accuracy.
• Experience selling AI, creative, or marketing technology is a plus.
• Excellent communication and interpersonal skills, with the ability to build and maintain relationships with stakeholders at all levels of an organization.
• Hungry, curious, resilient, and relentlessly resourceful.

Compensation

• This role will receive a competitive On-Target Earnings $300k+ (base salary + sales commission) + benefits + equity
• Quota: ~$1M
• Location: NYC-based (remote)

Reports to: CEO

Raspberry AI

Raspberry AI is a leading provider of industry-defining AI design software for fashion brands and retailers. Our software empowers brands to rapidly understand consumer demand and create unique designs within minutes. Leveraging cutting-edge AI analytics and generative AI capabilities, we help fashion brands revolutionize their design and merchandising processes.

We are a Series A startup, backed by top-tier venture capital firms such as Andreessen Horowitz, Khosla Ventures, MVP and Greycroft.

About the Role

We’re looking for a strategic and execution-driven Head of Customer Success to lead post-sales for our most important segment: enterprise customers. This is a pivotal role responsible for owning the pilot-to-expansion funnel, increasing conversion from pilot to multi-year contracts, and driving long-term account value.

You will be hands-on in working directly with our top enterprise customers, setting the bar for excellence in customer engagement and success. This role requires someone who can dive into the weeds, while also building and scaling repeatable processes.

You’ll help lead and grow the CSM team, setting clear goals and KPIs across conversion, revenue expansion, retention, and customer health. You’ll serve as both a strategic leader and coach—hiring and mentoring a high-performing team of CSMs and establishing a strong customer-centric culture. You'll also work cross-functionally with Sales, Product, and Marketing to surface customer insights and inform roadmap, messaging, and growth strategy.

Responsibilities

Customer Success Strategy

• Design and own our enterprise customer journey, from pilots to multi-year expansion
• Drive segmentation strategy for enterprise accounts to tailor engagement models by customer type, maturity, and strategic value.
• Build playbooks to maximize pilot conversion, value realization, onboarding, user engagement, and user adoption
• Establish strong relationships across executive sponsors, mid-level stakeholders, and user populations across enterprise clients

POC Conversion & Expansion

• Own pilot success plans and develop frameworks to consistently convert pilots into contracts
• Partner with Sales to shape deal structure and success metrics pre-sale
• Develop and track leading indicators of expansion potential across accounts, enabling early upsell motions.
• Lead quarterly business reviews (QBRs), executive alignment, and value storytelling

Team Leadership

• Build and lead a world-class CS team across customer success managers, solution architects, and training/support
• Implement team-wide rituals for knowledge sharing, deal retros, and continuous improvement across CS team
• Recruit, coach, and develop a high-performing team that thrives in technical and enterprise environments

Cross-functional Execution

• Serve as the voice of the customer to Product and Engineering teams, influencing roadmap based on enterprise needs
• Collaborate with Marketing on customer references, case studies, and product education
• Partner with Sales to track usage data, health scores, and renewal signals
  

Requirements

• 8+ years in customer success or post-sales leadership, with 4+ years managing enterprise CS teams at an Enterprise SaaS company with ACV over $200K
• At a minimum, managed 5+ CSMs or AEs responsible for post-sales
• Total Book Value (Managed ARR): minimum $10M ARR under team
• Direct experience managing accounts with ACV over $500K in high-touch motion
• Direct experience with enterprise sales cycles, especially pilot or POC-based land and expand motions
• Develop and operationalize data-driven playbooks and processes for onboarding, adoption/utilization, POC conversion, and expansion—anchored in clear KPIs such as time-to-value, NRR, pilot conversion rate, and account expansion velocity.
• Excellent executive presence, relationship building, communication, and value-selling capability
• Direct experience working cross-functionally with both Pre-sales and Training/User Enablement
• Experience building CS function from scratch in a high-growth environment
• Operationally rigorous with a bias for solution and experimentation
• Interest in fashion/retail clients
• Early stage or late stage startup experience

Nice to have

• Strong familiarity with generative AI tools
• Previous experience with fashion/retail clients
• Previous background managing creative stakeholders (design, marketing, ecommerce)
• Experience managing technical stakeholders, including innovation and IT teams

Reports to: Customer Success Lead

Raspberry AI

Raspberry AI is a leading provider of industry-defining AI design software for fashion brands and retailers. Our software empowers brands to rapidly understand consumer demand and create unique designs within minutes. Leveraging cutting-edge AI analytics and generative AI capabilities, we help fashion brands revolutionize their design and merchandising processes.

We are a Series A startup, backed by top-tier venture capital firms such as Andreessen Horowitz, Khosla Ventures, MVP and Greycroft.

About the Role

As an Enterprise Account Manager at Raspberry AI, you will own relationships with some of the world’s leading fashion brands and retailers, helping them transform their design and merchandising processes through generative AI. In this role, you will lead customer engagements from onboarding through upsells and renewal, ensuring teams not only leverage our platform effectively but also unlock measurable business outcomes.

You will serve as a key point of contact for our growing customer base, proactively engaging, supporting, and fostering strong, long-lasting relationships. This is an exciting opportunity to join a rapidly growing Series A SaaS company and directly contribute to our customers’ success and our overall growth.

Company Values

Customer obsession: We are relentlessly focused on our customers—their goals, their challenges, and their success. We listen deeply, move quickly to solve real needs, and obsess over delivering tools that make their lives easier, faster, and more creative.

Lowest level of detail: We are not afraid to get in the weeds. Great products are built by people who care enough to notice what others miss—the edge cases, the hidden friction, the opportunity behind the confusion. We train ourselves to ask deeper questions and uncover the details that unlock better work.

Be an owner: We take responsibility for outcomes, not just tasks. Whether fixing a bug, supporting a teammate, or raising a flag early—we step up. We do not wait for permission, and we do not pass the buck. Ownership is not a title; it is a mindset.

1% better every day: Progress compounds. We are committed to continuous improvement—in our product, our processes, and ourselves. Big leaps start with small steps, and we celebrate both. We stay curious, ask for feedback, and look for the extra 1% that makes tomorrow better than today.

Grow without fear: As Raspberry grows, we will face new challenges. To overcome them, each of us will be asked to grow alongside the company. We choose growth over comfort and learn from our mistakes.

Bias to solution: We all know “Bias to Action,” but what comes next? We do not just identify problems—we solve them. We are solutions-oriented at heart, pragmatic, and focused on what it takes to unblock ourselves and others.

Mission Statement

Help brands design and create looks that people love.

Responsibilities

Account Ownership & Growth: Own long-term relationships and commercial outcomes for a portfolio of fashion brands and retailers, including renewals, retention, and expansion. Drive strategic conversations with key decision-makers to help them maximize value from Raspberry AI. Manage the full post-sale lifecycle, ensuring seamless renewals and identifying upsell opportunities to expand platform usage.

Designing Value Realization: Partner with customer teams to define success metrics, create onboarding and adoption plans, and drive usage across their organizations. Guide brands in integrating Raspberry into design and merchandising workflows, ensuring measurable ROI. Facilitate regular business reviews to align on goals and uncover growth opportunities.

Proactive Customer Engagement: Monitor account health and product usage, proactively engaging customers to drive deeper adoption of key features. Accurately maintain customer information and interactions within our CRM, track key success metrics (e.g., usage, satisfaction), and identify churn risks early while leading resolution efforts.

Cross-functional Leadership: Work closely with Product, Engineering, and Support to surface feedback, influence the roadmap, and ensure timely resolution of issues. Collaborate with Sales to align on account strategy, pricing conversations, and long-term growth.

Contributing to Account Management Initiatives: Participate in team meetings and contribute to the ongoing improvement of account management processes and strategies. Develop resources (e.g., FAQs, knowledge base articles, customer case studies) and share them with relevant customers.

Qualifications

Background:

• Bachelor’s degree and relevant experience.
• ~6 years in a customer-facing role, ideally in enterprise SaaS account management, customer success, or strategy consulting.
• Experience in an early-stage start-up environment (<100 people).
  

Relationship Building:

• Demonstrated experience owning customer relationships, driving renewals, and securing expansions; Estimated ARR value of 3M+.
• Empathetic, customer-centric approach with a genuine desire to help customers succeed.
• Skilled at navigating complex organizations and identifying key decision-makers across functions.
• Ability to drive negotiations and lead difficult conversations with stakeholders.
  

Analytical Skills:

• Experience conducting ROI analyses and building financial models to demonstrate value.
• Skilled at analyzing usage trends and developing benchmarking models as needed.
• Proficient in building pricing models and performing calculations and discounts with precision.
  

Executive Communication:

• Ability to package insights into executive-level presentations and tell a compelling story.
• Demonstrated ability to tailor communication for different audiences (e.g., CFO vs. Creative Director).
• Strong verbal and written communication skills in a remote environment (e.g., email, Slack, stand-ups).
  

Cross-functional Collaboration:

• Ability to work independently and as part of a collaborative team in a fast-paced environment.
• Collaborate with cross-functional teams to expand the business:
  • Sales: Drive account growth.
  • Support: Direct attention to accounts at the right time.
  • Product: Communicate customer needs and help shape the roadmap.
    

Organization:

• Highly organized and detail-oriented, able to manage multiple tasks and prioritize effectively.
• Skilled at managing multiple projects and accounts with a high degree of accuracy and tracking.
  

Technology:

• Excitement about generative AI and exploration of available tools (e.g., ChatGPT, DALL·E, MidJourney).
• Proficiency in CRM software (e.g., HubSpot) and other customer success tools.

Bonus Points

• Familiarity with the fashion industry.

What We Offer

• Compensation range: $130–160K + OTE, with a competitive total compensation package.
• The opportunity to be part of a rapidly growing and exciting SaaS company.
• A collaborative and supportive work environment.
• Opportunities for professional growth and development.

Raspberry AI

Raspberry AI is a leading provider of industry-defining AI design software for fashion brands and retailers. Our software empowers brands to rapidly understand consumer demand and create unique designs within minutes. Leveraging cutting-edge AI analytics and generative AI capabilities, we help fashion brands revolutionize their design and merchandising processes.

We are a Series A startup, backed by top-tier venture capital firms such as Andreessen Horowitz, Khosla Ventures, MVP and Greycroft.

About the Role

This is a full-time remote role for a Senior Machine Learning Engineer at Raspberry AI. We are seeking a highly talented and motivated Machine Learning Engineer to join our growing ML team. In this role, you will focus on improving the quality and performance of our cutting-edge diffusion models, pushing the boundaries of generative AI in the fashion domain.

Additional responsibilities may be assigned as business needs evolve.

Responsibilities

• Conduct applied research and experimentation on state-of-the-art diffusion model architectures and training techniques.
• Implement and evaluate novel techniques for improving quality and controllability in generated designs.
• Analyze and interpret experimental results, draw meaningful conclusions, and communicate findings effectively.
• Collaborate closely with the team to translate prototypes into production-ready systems.
• Stay abreast of the latest advancements in diffusion models, deep learning, and generative AI research.

Requirements

• Master's or Ph.D. in Computer Science, Machine Learning, or a related field. 3+ years of industry experience.
• Strong theoretical and practical understanding of deep learning, with a focus on generative models (e.g., GANs, VAEs, Diffusion Models).
• Hands-on experience with deep learning frameworks such as PyTorch.
• Experience with training and evaluating generative models on cloud GPU platforms (e.g., AWS, GCP, Azure).
• Proficiency in using and tuning multimodal LLMs, including experience with both API-based and open-source model implementations.
• Ability to effectively present complex technical information to both technical and non-technical audiences.

Raspberry AI

Raspberry AI is a leading provider of industry-defining AI design software for fashion brands and retailers. Our software empowers brands to rapidly understand consumer demand and create unique designs within minutes. Leveraging cutting-edge AI analytics and generative AI capabilities, we help fashion brands revolutionize their design and merchandising processes.

We are a Series A startup, backed by top-tier venture capital firms such as Andreessen Horowitz, Khosla Ventures, MVP and Greycroft.

About the Role

This is a full-time remote role for a Principal Machine Learning Engineer at Raspberry AI. We are seeking a highly talented and motivated Machine Learning Engineer to join our growing ML team. In this role, you will focus on improving the quality and performance of our cutting-edge diffusion models, pushing the boundaries of generative AI in the fashion domain.

Additional responsibilities may be assigned as business needs evolve.

Responsibilities

• Conduct applied research and experimentation on state-of-the-art diffusion model architectures and training techniques.
• Implement and evaluate novel techniques for improving quality and controllability in generated designs.
• Analyze and interpret experimental results, draw meaningful conclusions, and communicate findings effectively.
• Collaborate closely with the team to translate prototypes into production-ready systems.
• Stay abreast of the latest advancements in diffusion models, deep learning, and generative AI research.

Requirements

• Master's or Ph.D. in Computer Science, Machine Learning, or a related field.
• 5+ years of industry experience.
• Strong theoretical and practical understanding of deep learning, with a focus on generative models (e.g., GANs, VAEs, Diffusion Models).
• Hands-on experience with deep learning frameworks such as PyTorch.
• Experience with training and evaluating generative models on cloud GPU platforms (e.g., AWS, GCP, Azure).
• Proficiency in using and tuning multimodal LLMs, including experience with both API-based and open-source model implementations.

Raspberry AI

Raspberry AI is a leading provider of industry-defining AI design software for fashion brands and retailers. Our software empowers brands to rapidly understand consumer demand and create unique designs within minutes. Leveraging cutting-edge AI analytics and generative AI capabilities, we help fashion brands revolutionize their design and merchandising processes.

We are a Series A startup, backed by top-tier venture capital firms such as Andreessen Horowitz, Khosla Ventures, MVP and Greycroft.

About the Role

Raspberry AI is seeking a full-time, remote AI Designer / Solutions Engineer with a strong background in luxury fashion design and presentation development to support client conversations, showcase our tools, and help fashion teams imagine new ways of working with AI. In this role, you’ll partner closely with Sales to design demos, prototype workflows, and communicate the value of our platform to prospects and customers.

The ideal candidate is visually fluent, confident presenting to both creative and technical audiences, and deeply knowledgeable about fashion trends, garment construction, and fabrication. You should be excited to talk with others about AI and how it’s changing the fashion industry. You’ll play a key role in building compelling examples, evaluating AI outputs, tailoring presentations for clients, and helping us test and improve our platform behind the scenes.

Additional responsibilities may be assigned as business needs evolve.

Responsibilities

• Design engaging presentation decks in Slides and Powerpoint that clearly communicate AI design capabilities
• Create custom visual assets to support internal initiatives and client-facing demos
• Create and execute tailored demos to showcase AI capabilities for specific audiences
• Offer expertise to colleagues from your luxury fashion design experience to improve our product
• Evaluate AI model outputs for quality, creativity, and alignment with design goals
• Benchmark platform performance against industry standards and internal expectations
• Conduct UX and stability testing of new tools and features; provide feedback to product and engineering teams
• Curate and organize fashion-specific datasets for model training and validation
• Label and structure data for targeted use cases such as sketch conversion and trend-driven generation
• Curate trends from various sources including runway, WGSN, Google, social media
• Participate in creating custom trend reports on behalf of our global clients
• Flexibility to take on new responsibilities as they arise.

Requirements

• 3-6 years of fashion industry experience, preferably working in Luxury fashion design
• Adobe Illustrator
• Adobe Photoshop
• Print Design
• Fashion Design
• Graphics
• Familiarity with generative AI tools (e.g., Midjourney, DALL·E, Runway)
• Google Docs, Slides, Spreadsheets
• MS365

Raspberry AI

Raspberry AI is a leading provider of industry-defining AI design software for fashion brands and retailers. Our software empowers brands to rapidly understand consumer demand and create unique designs within minutes. Leveraging cutting-edge AI analytics and generative AI capabilities, we help fashion brands revolutionize their design and merchandising processes.

We are a Series A startup, backed by top-tier venture capital firms such as Andreessen Horowitz, Khosla Ventures, MVP and Greycroft.

About the Role: We’re looking for a Senior Product Manager to lead product development efforts across our AI and fashion design tools. You’ll work closely with engineers, designers, and machine learning researchers to define and ship features that push the boundaries of what’s possible in generative design. You’ll be responsible for setting product strategy, prioritizing technical development, and ensuring our tools are intuitive and impactful for our users—designers and marketers at some of the world’s leading fashion brands.

Key Responsibilities:

• Own end-to-end product management for core features across our platform
• Define and document product requirements for AI- and ML-powered capabilities
• Daily collaboration with engineering and ML teams to scope and sequence technical roadmaps
• Collaborate with designers, product specialists, and customer success to translate user feedback and usage data into actionable product improvements
• Partner with the CTO to enhance our custom model training workflows
• Prioritize features that drive adoption, engagement, and design outcomes for fashion teams
• Leverage Amplitude and internal analytics tools to surface insights and inform product prioritization
• Communicate product vision, KRs, updates, and outcomes clearly across internal stakeholders

Qualifications:

• 5+ years of experience in product management in B2B SaaS, workflow products or applied AI
• Proven track record of building and launching new user-facing significant products
• Demonstrated success launching and scaling technical products
• Strong ability to synthesize technical complexity into user-first solutions
• Experience working closely with engineers, designers, and ML practitioners
• Excellent communication, prioritization, and organizational skills
• Passion for generative AI, creativity tools, or the fashion industry
• (Bonus) Familiarity with AI/ML development cycles

Benefits:

• Competitive salary and equity options
• Comprehensive benefits package including 401k, health, dental, and vision insurance
• Opportunity to work on cutting-edge AI technology with a high-impact team
• Fully remote and a supportive company culture
• Be part of a rapidly growing company with significant growth potential