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Account Executive – AI Career Guidance Evaluator

Alignerr

AI & Data Training Contractor
Remote (Global) $25 – $50/hr June 16, 2026

Job description

Account Executive – AI Career Guidance Evaluator

About the Role

What if your hands-on experience closing deals and managing pipelines could directly improve how AI coaches sales professionals around the world? We're looking for experienced Account Executives and B2B sales professionals in the Chicago area to evaluate and improve next-generation AI career guidance systems.

This is a fully remote, flexible contract role built for working professionals. No AI background needed — just deep expertise in sales and a genuine ability to recognize great career advice when you see it.

  • Organization: Alignerr
  • Type: Hourly Contract
  • Location: Remote
  • Commitment: 10–40 hours/week

What You'll Do

  • Review career-related questions submitted by professionals at different stages of their sales careers
  • Write high-quality "golden answers" that reflect expert-level career guidance for Account Executives and B2B sales professionals
  • Create objective evaluation rubrics used to assess AI-generated career advice
  • Identify inaccurate, unrealistic, or incomplete recommendations generated by AI systems
  • Contribute your real-world industry knowledge to improve AI career coaching capabilities
  • Work independently and asynchronously on your own schedule

Who You Are

  • Proven professional experience as an Account Executive or B2B Sales Professional
  • Strong understanding of sales career progression, pipeline management, prospecting, and closing strategies
  • Experience mentoring or coaching sales professionals is highly valued
  • Excellent written communication skills — you can translate real-world experience into clear, actionable guidance
  • Able to provide practical, realistic career advice grounded in actual field experience
  • No prior AI or tech experience required

Nice to Have

  • SaaS or technology sales experience
  • Enterprise or mid-market sales background
  • Sales leadership, management, or team lead experience
  • Consistent record of quota attainment
  • Background in sales training, onboarding, or professional development

Why Join Us

  • Help shape how AI systems provide career guidance to sales professionals worldwide
  • Fully remote and flexible — work when and where it suits you
  • Freelance autonomy with the structure of meaningful, task-based work
  • Contribute expertise from your profession to cutting-edge AI evaluation projects
  • Potential for ongoing work and long-term opportunities as new projects launch
Apply now

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