Strategic Account Executive

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 are backed by Andreessen Horowitz and growing rapidly. For more information, visit raspberry.ai.

• 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.

• 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.

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.

• Own the full sales cycle from prospecting through close and expansion, with a focus on annual and multi-year contracts.

• Develop multi-threaded relationships across Marketing, Innovation, IT, and Procurement at target accounts.

• Craft ROI-driven executive narratives and business cases tailored to each stakeholder and buying committee.

• Build self-sourced pipeline through outbound, events, and social proximity — not just sequences.

• Navigate complex negotiations end-to-end, including legal, procurement, and compliance processes.

• Collaborate with Product, CS, and Marketing on account strategy and expansion planning.

• 5+ years of Account Executive experience supporting complex B2B SaaS, Developer Tools, or AI/ML products in the NYC region

• Average deal size of $750K+ ACV

• Proven experience driving revenue outcomes, including owning a revenue quota and identifying, qualifying, and closing cross-sell opportunities along with renewals at scale

• Strong automation first mindset - you thrive in delivering a digital customer journey across 150+ accounts and finding ways to personalize at scale

• 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.

• This role will receive a competitive On-Target Earnings $300k+ (base salary + sales commission) + benefits + equity

• Location: NYC