Head of Enterprise Sales

🕒 June 2

🗽 New York – Remote

🗽 New York – Remote

⏰ Full Time

🔴 Lead

🤑 Sales

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Raspberry AI

WebsiteLinkedInAll Job Openings

11 - 50 employees

🤖 Artificial Intelligence

👗 Fashion

☁️ SaaS

Artificial Intelligence • Fashion • SaaS

Raspberry AI is a generative AI platform and creative assistant for fashion brands and designers that automates design and visual content creation. It generates prints, patterns, product graphics, and photorealistic renderings (sketch-to-render, photography and video studio outputs), and offers brand-customized AI models, private hosting, and enterprise workflows to speed concept-to-market, reduce sampling costs, and retain IP. The product is positioned as a B2B SaaS tool used by retailers, apparel manufacturers, and design teams to iterate faster and scale visual merchandising and product development.

📋 Description

• 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.

🎯 Requirements

• 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.

🏖️ Benefits

• 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.