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Simple AISimple AI

Head of Sales

The first Head of Sales will own enterprise revenue, personally close major deals, and build a repeatable sales motion while hiring and coaching the team. The role requires 7+ years of B2B SaaS sales experience, strong enterprise deal judgment, and a track record of exceeding large quotas.

About the job

Responsibilities

  • Own the revenue number and lead the company’s next phase of enterprise growth.
  • Personally prospect, run discovery, shape business cases, navigate complex buying committees, negotiate, and close high-impact enterprise deals.
  • Build the sales motion, territories, team, and playbooks from an early stage.
  • Hire and coach quota-carrying sellers in a hands-on player-coach capacity.
  • Manage pipeline rigorously and forecast accurately.
  • Partner with Product, Engineering, Forward Deployed Engineers, Solutions Engineers, and other customer-facing technical teams.
  • Lead outbound selling, multi-threaded discovery, executive alignment, technical evaluations, security, legal, and procurement processes.

Requirements

  • 7+ years of B2B SaaS sales experience.
  • Experience leading or coaching quota-carrying sellers in an early-stage or high-growth company.
  • Track record of personally exceeding seven-figure annual quotas and repeatedly closing six-figure enterprise deals.
  • Experience building a sales motion, territory, team, or playbook from an early stage.
  • Strong enterprise deal judgment.
  • Rigorous pipeline management and forecasting skills.
  • High agency, urgency, and low ego.
  • Willingness and enthusiasm to work in person with the team in San Francisco.

Nice to Have

  • Experience selling AI, automation, developer tools, or another technical enterprise product.
  • Experience selling to contact center, customer experience, operations, or revenue leaders.
  • Experience partnering closely with founders, engineers, Forward Deployed Engineers, or Solutions Engineers on complex deals.

Compensation & Benefits

  • Competitive salary and meaningful equity.
  • Employee-friendly equity terms.
  • Health, dental, and vision insurance.
  • Free lunch and dinner at the office.
  • Commute assistance.
  • Regular team events and offsites.
  • Office located in San Francisco.

Skills

B2B SaaS, Enterprise Sales, Sales Strategy, Pipeline Management, Sales Forecasting, Outbound Sales, Discovery, Business Cases, Negotiation, Quota Management, Technical Evaluations, Security Reviews, Procurement, Artificial Intelligence, Automation

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