Head of Enterprise Sales

This is a fully remote position, open to applicants in New York.

📋 Description

• Lead, mentor, and develop a team of Enterprise Account Executives (AEs), Strategic AEs, and Business Development Representatives (BDRs) to consistently surpass pipeline and revenue goals.

• Collaborate closely with the VP of Revenue to establish and implement the company's enterprise sales strategy.

• Promote disciplined sales execution through effective pipeline management, forecasting, deal evaluations, and quota achievement.

• Recruit, onboard, and support the ramp-up of new sales personnel as the team expands to 10–15 AEs.

• Create and refine playbooks, outbound strategies, and sales processes that facilitate repeatable and scalable growth.

• Engage cross-functionally with Marketing, Product, and Customer Success to align on Ideal Customer Profile (ICP), messaging, and expansion opportunities.

• Leverage data to identify performance gaps and provide coaching for individual improvement.

• Represent the sales team in leadership and planning discussions, including forecasting and pipeline assessments.

⛳️ Requirements

• Over 10 years of experience in B2B SaaS/AI sales, including at least 3 years in a sales management position.

• Demonstrated success in leading enterprise and/or strategic AEs to exceed quotas in a fast-paced, high-growth setting.

• Experience in managing or closely collaborating with BDR/SDR teams.

• Strong discipline in pipeline management and forecasting; adept at utilizing a CRM (Salesforce preferred).

• Exceptional coaching and talent development abilities — you excel at bringing out the best in your team.

• Ability to thrive in ambiguous, early-stage environments where building is as important as managing.

• Excellent communication skills and executive presence — capable of engaging with C-suite buyers and internal stakeholders alike.

• Experience selling into the fashion, retail, or similar sectors is an advantage but not mandatory.

🏝️ Benefits

• Innovative culture: A unique opportunity to shape the role of AI within one of the world's largest industries.

• Growth paths: Opportunities to create an impact that extends well beyond your immediate responsibilities as the company grows.

• Learning & development: Annual discretionary stipend for professional growth and development.

• Annual company offsite: An opportunity to gather the entire team together once a year.