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New York City, United States

Generative AI Trainer

AJAIA · New York City · United States

AI Trainer / Data Annotator

Posted: 6/1/2026 · Last checked: 10/11/2026

Job description

Quoted in full from AJAIA's job posting. Gavroche does not edit it.

About the Company

Ajaia is a rapidly growing AI consultancy and product studio dedicated to helping organizations move from experimentation to real results. We operate across four core pillars: AI Strategy and Advisory, AI Engineering and Automation, Workforce Training and Enablement, and Custom Product Development.

In addition to client services, Ajaia builds proprietary AI products, copilots, and vertical solutions that solve high-value industry problems. This dual model allows us to translate hands-on implementation experience into scalable products while continuously refining our approach through real-world deployment.

Our operating model combines deep technical execution with practical change management, enabling enterprises to deploy secure, compliant, and high-impact solutions that drive measurable operational value. Mission: Help organizations win the AI moment.

Position Overview

We are looking for high-caliber professionals who can bridge the gap between AI potential and corporate reality. This is not a role for theoretical educators; it is for authoritative practitioners who can command a room and demonstrate how AI solves high-value industry problems in real-time.

You will be responsible for the Workforce Training and Enablement pillar. You will move beyond slides to show enterprise teams exactly how to integrate AI into their specific professional workflows. We are seeking "smart, well-presenting" individuals with a background that commands immediate respect from sophisticated audiences.

Primary Responsibilities

  • Deliver live, high-impact training sessions that prioritize practical application over theoretical design.
  • Execute real-time demonstrations of AI-native workflows, showcasing skills like automated synthesis, planning, and delivery acceleration.
  • Communicate with authority to professional audiences, ensuring AI concepts are translated into immediate operational value.
  • Drive workforce adoption by ensuring training outcomes produce clear business results.
  • Use AI tools to enhance estimation quality, personalize training modules, and support decision-making.
  • Ensure all training programs produce clear business outcomes and measurable operational value.

Job Requirements

  • Credible Professional Background: A sophisticated track record in high-performance fields (e.g., Finance, Consulting, Legal, or Strategy).
  • AI-Native Mastery: Demonstrated experience using AI tools and automation in a practical, daily professional context.
  • Exceptional Communication: The ability to present to, influence, and educate executive-level stakeholders with confidence.
  • Execution Mindset: A focus on shipped outcomes and measurable adoption rather than theoretical learning.
  • Adaptable Presence: Ability to manage ambiguity and shifting priorities in fast-moving environments.

Schedule and Location

  • Location: Remote (US) or Hybrid (based on project needs).
  • Schedule: 1099 Contractor; work hours are as needed with no fixed shift.
  • Travel: Limited client travel may be required.

Compensation and Benefits

Compensation (USD/year):

  • Base Rate: $75-$100/hour
  • Structure: 1099 Contractor.
  • Bonus: High-upside, performance-based bonus potential tied to delivery quality and client outcomes.

Benefits:

  • Competitive compensation with performance upside
  • Professional development support

Why Join Ajaia

You will have direct ownership of AI educational outcomes in a fast-scaling consultancy where execution quality is paramount. This role offers high-impact exposure to founders and enterprise leaders, with the opportunity to contribute to real innovation at the AI frontier. We expect all team members to be AI-native practitioners who use AI daily to improve speed and quality.

Experience the Ajaia difference. Let's build what's next.

Requirements

Job Requirements

  • Credible Professional Background: A sophisticated track record in high-performance fields (e.g., Finance, Consulting, Legal, or Strategy).
  • AI-Native Mastery: Demonstrated experience using AI tools and automation in a practical, daily professional context.
  • Exceptional Communication: The ability to present to, influence, and educate executive-level stakeholders with confidence.
  • Execution Mindset: A focus on shipped outcomes and measurable adoption rather than theoretical learning.
  • Adaptable Presence: Ability to manage ambiguity and shifting priorities in fast-moving environments.

Benefits

Compensation (USD/year):

  • Base Rate: $75-$100/hour
  • Structure: 1099 Contractor.
  • Bonus: High-upside, performance-based bonus potential tied to delivery quality and client outcomes.

Benefits:

  • Competitive compensation with performance upside
  • Professional development support

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