About OpenTrain
OpenTrain AI is the hiring and contracting organization for this remote project. OpenTrain is the #1 platform for finding and building careers in AI training and data labeling, helping contributors discover opportunities, build a professional profile, and grow a lasting portfolio of AI work.
About AI Training Work
AI training is the human side of building modern artificial intelligence. Experienced professionals create examples, assess model responses, and provide expert feedback so AI systems can produce more accurate, useful, and credible guidance in real-world settings.
In this project, your enterprise sales judgment will help train AI systems to reason through complex B2B sales situations, from prospecting and discovery through negotiation, forecasting, and deal closure.
The Role
OpenTrain is seeking a B2B Sales AI Training Expert to create, evaluate, and refine complex sales tasks and solutions. You will translate practical enterprise selling experience into accurate, strategic, and customer-focused AI training content.
The work covers complex B2B and enterprise scenarios and is performed under senior review. You will incorporate calibration feedback and apply quality standards established by the functional expert lead.
• Remote contractor engagement lasting up to 9 weeks
• Expected commitment of at least 4 hours per day and up to 40 hours per week
• At least 4 hours of overlap with Pacific Time required
• English-language work
• Worldwide applicants may be considered
• Compensation is not disclosed
What You'll Do
• Create expert sales tasks and solutions for complex B2B and enterprise scenarios
• Evaluate and refine AI outputs for commercial accuracy, strategic quality, and practical usefulness
• Develop content covering account planning, opportunity qualification, competitive positioning, negotiation, and deal strategy
• Address pipeline management, forecasting, risk identification, and deal closure
• Build scenarios involving executive sponsors, technical evaluators, procurement, legal, and finance stakeholders
• Apply practical judgment to multi-stakeholder buying groups and complex sales cycles
• Work under senior review, incorporate calibration feedback, and follow functional quality standards
Requirements
This project is designed for experienced sales professionals who can apply real-world commercial judgment to AI training work. You should have a strong record of navigating complex enterprise deals and turning sales expertise into clear, accurate evaluations and recommendations.
• 8–15 years of quota-carrying B2B or enterprise sales experience
• Experience managing strategic accounts and complex, multi-year enterprise deal cycles
• Consistent record of meeting or exceeding revenue targets
• Track record of closing high-value, multi-year enterprise deals
• Command of MEDDIC, MEDDPICC, Challenger, SPIN, or an equivalent formal sales methodology
• Expertise in qualification, commercial negotiation, forecasting, competitive positioning, and deal strategy
• Ability to navigate executive sponsors, technical evaluators, procurement, legal, and finance stakeholders
• Strong capabilities in account planning, pipeline management, risk identification, executive engagement, and cross-functional deal coordination
• Bachelor's degree or equivalent practical experience
Helpful Background
Experience in AI evaluation, data annotation, content review, quality assurance, or a related analytical role is helpful but not required. The most important foundation is substantial enterprise sales experience and the ability to assess whether sales guidance is commercially sound and practically useful.
Why Work With OpenTrain
AI training and data-labeling work is a fast-growing part of the technology industry. Contributors with specialized expertise can help shape how advanced AI systems understand professional scenarios and respond to complex real-world questions.
OpenTrain gives you a place to build a credible AI training portfolio, discover projects aligned with your skills, and develop a longer-term path in this emerging field. Creating an OpenTrain account is free.