Head of Enterprise SalesRaspberry AI • New York, NY • Full-Time
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- 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.
