Head of Enterprise Sales

Head of Enterprise Sales Raspberry AI · New York, NY · Full-Time About Raspberry AI 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. For more information, visit raspberry.ai . 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. About the role 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. Responsibilities • Lead, coach, and develop a team of Enterprise AEs, Strategic AEs, and BDRs to consistently exceed pipeline and revenue targets. • Partner closely with the VP of Revenue to define and execute the company's enterprise sales strategy. • Drive disciplined sales execution: pipeline management, forecasting, deal reviews, and quota attainment. • Recruit, onboard, and ramp new sales hires as the team scales to 10–15 AEs. • Build and iterate on playbooks, outbound motions, and sales processes that support repeatable, scalable growth. • Work cross-functionally with Marketing, Product, and Customer Success to align on ICP, messaging, and expansion opportunities. • Use data to identify performance gaps and coach individuals toward improvement. • Represent the sales organization in leadership and planning discussions, including forecasting and pipeline reviews. Qualifications • 10+ years of B2B SaaS/AI sales experience, with at least 3 years in a sales management role. • Proven track record of leading enterprise and/or strategic AEs to exceed quota in a fast-paced, high-growth environment. • Experience managing or closely collaborating with BDR/SDR teams. • Strong pipeline management and forecasting discipline; comfortable working in a CRM (Salesforce preferred). • Excellent coaching and people development skills — you know how to bring out the best in your team. • Comfort operating in ambiguous, early-stage environments where you'll need to build as much as manage. • Outstanding communication and executive presence — able to engage with C-suite buyers and internal stakeholders alike. • Experience selling into fashion, retail, or adjacent verticals is a plus but not required. Raspberry AI is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.