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