Demo

Head of Sales

Draft labs
Miami, FL Full Time
POSTED ON 10/13/2026
AVAILABLE BEFORE 11/11/2026

We are hiring a Head of Sales to build and lead our go-to-market motion for an AI data infrastructure company serving leading AI labs and enterprises.

We work with companies building and deploying AI systems, helping them access high-quality human data, model evaluations, red teaming, computer-use trajectories, domain-specific annotation, and agent workflow training. We are looking for a sales leader who can own enterprise pipeline, close high-value customer relationships, and build the foundation for a repeatable sales engine.

This is a founding GTM role. You will work directly with the founders, own customer conversations from first touch through close, and help define how we sell into AI labs, enterprise AI teams, and companies building internal AI systems.

Responsibilities:

  • Own outbound and inbound sales across AI labs, enterprise AI teams, and AI infrastructure customers
  • Build and manage pipeline from prospecting through close
  • Lead discovery calls, demos, pricing conversations, pilots, and commercial negotiations
  • Work with founders to refine ICP, messaging, pricing, and sales process
  • Convert early customer demand into repeatable sales playbooks
  • Coordinate with operations and delivery teams to make sure customer needs are scoped clearly
  • Track pipeline, conversion, customer feedback, and revenue targets
  • Help hire and build the future sales team as the company scales

Ideal candidates:

  • Experience selling to enterprises, AI/ML teams, data teams, engineering teams, or technical buyers
  • Strong outbound ability and comfort creating pipeline from scratch
  • Experience closing mid-market or enterprise deals
  • Comfortable selling a new category before the market is fully defined
  • Strong written and verbal communication
  • Highly organized, founder-level urgency, and willing to do hands-on work
  • Bonus: experience in AI, data labeling, model evaluation, developer tools, infrastructure, or technical services

Compensation:

  • Competitive salary plus commission and equity
  • Full-time role
  • Remote or hybrid depending on location

Requirements:

  • 4 years of sales, business development, or GTM experience
  • Experience owning quota or closing customer relationships
  • Ability to operate independently in an early-stage startup environment
  • Comfort selling technical products or services to sophisticated buyers

Type of position:
Full-time employee

Work experience:
4 years preferred

Salary : $70,000 - $125,000

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