Account Executive – AI Career Guidance Evaluator

About the role

This is a fully remote, flexible contract role. No AI or technology background required — just real, hard-won experience in sales and a clear sense of what practical career advice looks like.

What You'll Do

• Review career-related questions submitted by professionals at different stages of their sales journey
• Write high-quality "golden answers" that reflect expert-level career guidance within the Account Executive and B2B sales field
• Develop objective evaluation rubrics to assess AI-generated career advice
• Identify inaccurate, unrealistic, or incomplete AI recommendations
• Apply your real-world sales knowledge to improve how AI models coach and advise professionals
• Work independently and asynchronously on your own schedule

Who You Are

• Proven professional experience as an Account Executive or B2B Sales Professional
• Strong working knowledge of sales career progression, pipeline management, prospecting, and closing
• Experience mentoring or coaching junior sales professionals is highly valued
• Excellent written communication skills
• Able to translate lived experience into practical, actionable career guidance
• No prior AI or tech experience required

Nice to Have

• SaaS or technology sales background
• Enterprise or mid-market sales experience
• Sales leadership or management experience
• Consistent track record of quota attainment
• Experience in sales training, enablement, or onboarding programs

Why Join Us

• Help define how AI systems support career development for sales professionals
• Fully remote and flexible — work when and where it suits you
• Freelance autonomy with the structure of meaningful, task-based work
• Contribute your professional expertise directly to cutting-edge AI projects
• Potential for ongoing work and long-term opportunities as new projects launch