Head of Enterprise Sales

Raspberry AI•New York, NY

3d•Onsite

About The Position

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.

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.

Nice To Haves

Experience selling into fashion, retail, or adjacent verticals is a plus but not required.

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.