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Head of Enterprise Sales

June 3, 2026

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

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...