Enterprise Sales AI Training Expert

OpenTrain AI; Northern (KY); Hybrid; USD 83,000 - 124,000; Part time

Job summary

OpenTrain AI is seeking an Enterprise Sales AI Training Expert to evaluate and improve AI performance on real-world enterprise sales work. You will audit multi-step workflows, create golden reference examples, and refine the rubrics used to distinguish excellent selling from average performance.

This is a fully remote contractor opportunity for candidates located in the United States. The role is associated with a 40-hour-per-week commitment in the description, while the structured listing

Qualifications

• Around 10 years of hands-on enterprise sales experience.
• Consistent track record of meeting or exceeding sales quotas.
• Fluency with Salesforce, Jira, Confluence, Google Workspace, and Microsoft Office.
• Deep experience with CRM administration and data-driven reporting.
• Strong writing skills for professional customer-facing materials.
• English fluency and eligibility to work from the United States.

Responsibilities

• Review enterprise sales workflows and assess AI performance against a strong seller.
• Build golden trajectories by completing sales tasks end to end.
• Work across prospecting, pipeline management, CRM hygiene, reporting, and customer-facing documents.
• Pressure-test and refine evaluation rubrics for sales performance.
• Operate across test environments modeled on CRM, communication, and billing tools.
• Create polished pitches, slide decks, summaries, and other customer-facing materials.

Skills

Enterprise sales

Sales quotas

CRM experience

Salesforce

Jira

Confluence

Google Workspace

Microsoft Office

Written communication

Tools

Salesforce

Jira

Confluence

Google Workspace

Microsoft Office

Job description

About OpenTrain

OpenTrain AI is the hiring and contracting organization for this opportunity. OpenTrain is the #1 platform for finding and building careers in AI training and data labeling, helping people discover projects, build a professional profile, and apply in minutes.

• Free account creation and profile building
• Remote opportunities across the growing AI training industry
• A flexible way to develop experience teaching and evaluating AI systems

About AI Training Work

AI training is the human side of building artificial intelligence. Specialists review model behavior, create high-quality examples, and design evaluation standards that help AI systems perform useful work more accurately.

In this role, your enterprise sales knowledge will help shape how an AI system handles realistic sales workflows, from prospecting and pipeline management to customer-facing communication and reporting.

• Work directly on cutting-edge AI evaluation
• Apply practical professional judgment to realistic business tasks
• Contribute to systems that learn from expert-reviewed examples

The Role

OpenTrain AI is seeking an Enterprise Sales AI Training Expert to evaluate and improve AI performance on real-world enterprise sales work. You will audit multi-step workflows, create golden reference examples, and refine the rubrics used to distinguish excellent selling from average performance.

This is a fully remote contractor opportunity for candidates located in the United States. The role is associated with a 40-hour-per-week commitment in the description, while the structured listing specifies availability of 20 or more hours per week. Pay is $60-$90 per hour.

• Location: United States
• Language: English
• Work arrangement: Fully remote
• Engagement: Contractor and part-time
• Pay: $60-$90 per hour
• Availability: 20 or more hours per week; the role description calls for 40 hours per week

What You'll Do

You will work in test environments designed to mirror a real sales technology stack. Your judgment will help determine whether an AI system can execute complex enterprise sales work with the quality, consistency, and business awareness expected from a strong seller.

• Review multi-step enterprise sales workflows and assess whether the AI handled them like a strong seller
• Build golden trajectories by completing sales tasks end to end
• Work across prospecting, pipeline management, CRM hygiene, reporting, and customer-facing documents
• Pressure-test and refine evaluation rubrics for sales performance
• Operate across test environments modeled on CRM, communication, and billing tools
• Create polished pitches, slide decks, summaries, and other customer-facing materials

Requirements

This opportunity requires substantial hands-on enterprise sales experience and a strong understanding of the full sales cycle. You should be comfortable translating practical sales judgment into clear examples, written feedback, and measurable evaluation criteria.

• Around 10 years of hands-on enterprise sales experience, with the additional requirements listing 10 or more years
• A consistent, proven track record of meeting or exceeding sales quotas
• Day-to-day fluency with Salesforce, Jira, Confluence, Google Workspace, and Microsoft Office
• Deep experience with CRM administration, sales process management, pipeline tracking, and data-driven reporting
• Strong writing skills for polished, professional customer-facing materials
• English fluency and eligibility to work from the United States

Helpful Background

Experience working within or alongside a two-sided, AI-powered B2B SaaS creator marketplace is helpful. Familiarity with outcome-based campaigns and troubleshooting across a connected technology stack can also support success in this role.

• Experience with AI-powered B2B SaaS marketplaces
• Exposure to outcome-based campaigns
• Experience troubleshooting workflows across connected sales, communication, and billing tools

Who Should Apply

This role may suit an experienced enterprise seller, sales operations leader, CRM specialist, or revenue professional who can evaluate complex sales execution and explain what high-quality work looks like. The structured listing labels the opportunity as entry level, but the stated role requirements call for 10 or more years of enterprise sales experience.

• Enterprise sales professionals with full-cycle experience
• Sales leaders who can distinguish strong execution from weak execution
• CRM and pipeline experts with strong operational judgment
• Clear writers who can produce customer-ready business materials
• Professionals interested in helping shape how AI performs enterprise work