Account Executive – AI Career Guidance Evaluator

Account Executive – AI Career Guidance Evaluator

About the Role

Toronto is one of North America's fastest-growing tech and sales markets — and we want people who know what it takes to succeed in it. We're looking for experienced Account Executives and B2B sales professionals to help train, evaluate, and improve next-generation AI career guidance systems.

Your expertise will directly shape how AI models advise sales professionals at every career stage — from first quota to enterprise leadership. This is a fully remote, flexible contract role open to working professionals. No AI background required.

• 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
• Develop 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 other sales professionals is a significant asset
• Excellent written communication skills in English
• Able to provide practical, realistic career advice grounded in real field experience
• No prior AI or tech experience required

Nice to Have

• SaaS or technology sales experience — particularly relevant in Toronto's thriving tech sector
• Enterprise or mid-market sales background
• Sales leadership, management, or team-building experience
• Consistent track record of quota attainment
• Background in sales training, coaching, or professional development programs

Why Join Us

• Help define how AI systems deliver 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 your professional expertise to cutting-edge AI evaluation projects
• Potential for ongoing work and long-term opportunities as new projects launch