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<h1><strong>Head of Enterprise Sales</strong></h1><p style="min-height:1.5em">Raspberry AI · New York, NY · Full-Time</p><p style="min-height:1.5em"><strong>About Raspberry AI</strong></p><p style="min-height:1.5em">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.</p><p style="min-height:1.5em">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. For more information, visit <a target="_blank" rel="noopener noreferrer nofollow" href="http://raspberry.ai">raspberry.ai</a>.</p><p style="min-height:1.5em"><strong>How we work</strong></p><ul style="min-height:1.5em"><li><p style="min-height:1.5em"><strong>Be an owner:</strong> 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.</p></li><li><p style="min-height:1.5em"><strong>Bias to solution:</strong> We're solutions-oriented at heart. We go beyond identifying problems to actively unblocking ourselves and others.</p></li><li><p style="min-height:1.5em"><strong>Customer obsession:</strong> 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.</p></li><li><p style="min-height:1.5em"><strong>Lowest level of detail:</strong> We're not afraid to get in the weeds. Great work comes from people who notice what others miss and ask deeper questions.</p></li><li><p style="min-height:1.5em"><strong>1% better every day:</strong> Progress compounds. We stay curious, ask for feedback, and look for the small improvements that make tomorrow better than today.</p></li><li><p style="min-height:1.5em"><strong>AI first:</strong> We use AI across the entire company — from product to growth to operations — to move faster and produce higher-quality work.</p></li></ul><p style="min-height:1.5em"><strong>What we offer</strong></p><ul style="min-height:1.5em"><li><p style="min-height:1.5em"><strong>Innovative culture:</strong> A generational opportunity to define the role of AI in one of the world's largest industries.</p></li><li><p style="min-height:1.5em"><strong>Growth paths:</strong> Opportunities to drive impact well beyond your immediate role as the company scales.</p></li><li><p style="min-height:1.5em"><strong>Learning & development:</strong> Annual discretionary stipend for professional development.</p></li><li><p style="min-height:1.5em"><strong>Annual company offsite:</strong> We bring the whole team together once a year.</p></li></ul><p style="min-height:1.5em"><strong>About the role</strong></p><p style="min-height:1.5em">We are looking for a Head of Sales to build and lead our revenue-generating field organization. Reporting directly to our VP of Revenue, you will manage a growing team of Enterprise Account Executives, Strategic Account Executives, and Business Development Representatives as we scale to 10–15 AEs this year. This is a hands-on leadership role for someone who thrives at the intersection of coaching, pipeline development, and cross-functional GTM execution.</p><p style="min-height:1.5em"><strong>Responsibilities</strong></p><ul style="min-height:1.5em"><li><p style="min-height:1.5em">Lead, coach, and develop a team of Enterprise AEs, Strategic AEs, and BDRs to consistently exceed pipeline and revenue targets.</p></li><li><p style="min-height:1.5em">Partner closely with the VP of Revenue to define and execute the company's enterprise sales strategy.</p></li><li><p style="min-height:1.5em">Drive disciplined sales execution: pipeline management, forecasting, deal reviews, and quota attainment.</p></li><li><p style="min-height:1.5em">Recruit, onboard, and ramp new sales hires as the team scales to 10–15 AEs.</p></li><li><p style="min-height:1.5em">Build and iterate on playbooks, outbound motions, and sales processes that support repeatable, scalable growth.</p></li><li><p style="min-height:1.5em">Work cross-functionally with Marketing, Product, and Customer Success to align on ICP, messaging, and expansion opportunities.</p></li><li><p style="min-height:1.5em">Use data to identify performance gaps and coach individuals toward improvement.</p></li><li><p style="min-height:1.5em">Represent the sales organization in leadership and planning discussions, including forecasting and pipeline reviews.</p></li></ul><p style="min-height:1.5em"><strong>Qualifications</strong></p><ul style="min-height:1.5em"><li><p style="min-height:1.5em">10+ years of B2B SaaS/AI sales experience, with at least 3 years in a sales management role.</p></li><li><p style="min-height:1.5em">Proven track record of leading enterprise and/or strategic AEs to exceed quota in a fast-paced, high-growth environment.</p></li><li><p style="min-height:1.5em">Experience managing or closely collaborating with BDR/SDR teams.</p></li><li><p style="min-height:1.5em">Strong pipeline management and forecasting discipline; comfortable working in a CRM (Salesforce preferred).</p></li><li><p style="min-height:1.5em">Excellent coaching and people development skills — you know how to bring out the best in your team.</p></li><li><p style="min-height:1.5em">Comfort operating in ambiguous, early-stage environments where you'll need to build as much as manage.</p></li><li><p style="min-height:1.5em">Outstanding communication and executive presence — able to engage with C-suite buyers and internal stakeholders alike.</p></li><li><p style="min-height:1.5em">Experience selling into fashion, retail, or adjacent verticals is a plus but not required.</p></li></ul><p style="min-height:1.5em"><em>Raspberry AI is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.</em></p>
