Head of Enterprise Sales

Raspberry AI

Head of Enterprise Sales leading revenue generation for Raspberry AI. Coaching a growing team of sales professionals while executing sales strategy with a focus on AI for fashion brands.

Posted 6/2/2026full-timeRemote • New York • 🇺🇸 United StatesLeadWebsite

About the role

Key responsibilities & impact

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

What you’ll need

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

Comp & perks

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.

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

B2B salesSaaS salesAI salespipeline managementforecastingquota attainmentsales strategycoachingpeople development

Soft Skills

leadershipcommunicationexecutive presenceteam developmentcross-functional collaborationdata analysisproblem-solvingadaptabilityengagement