Enterprise Sales AI Training Expert (CRM & Workflows)

About OpenTrain

OpenTrain is the #1 platform for people who build careers in AI training and data labeling. We connect experienced contributors with hands-on projects that shape how real AI systems behave, and we hire and contract directly for this role.

Working with OpenTrain means joining a fast-growing industry where human expertise — like your enterprise sales knowledge — directly guides model behavior and outcomes.

Why AI training matters (and why sellers join)

AI training is the human side of building AI: people create examples, review outputs, and teach models the decision-making skills they need. That work is remote, flexible, and accessible to practitioners across industries.

For sales professionals, AI training is a chance to codify best practices, influence model behavior for real-world workflows, and turn deep hands-on experience into high-impact, paid project work.

The Role

OpenTrain is hiring an Enterprise Sales AI Training Expert to help teach and evaluate an AI model on complex, multi-step enterprise sales workflows. You will join a team of seasoned sellers to set the standard for excellent AI sales behavior.

This is a US-remote contractor role (part-time, 20+ hours/week) paying $60–$90 per hour. You will audit model outputs, create golden reference examples, and shape the evaluation rubrics that determine model performance.

• Location: United States (remote)
• Employment type: Contractor, Part-time (20+ hours/week)
• Pay: $60–$90 per hour

What you'll do

You will work hands-on inside simulated sales environments and evaluation tools to teach and measure AI behavior across the end-to-end seller workflow.

• Review multi-step enterprise sales workflows and judge whether the AI handled them correctly.
• Build golden trajectories by completing real sales tasks end-to-end — prospecting, pipeline management, CRM hygiene, reporting, and customer-facing documents.
• Pressure-test and refine evaluation rubrics to capture what separates great selling from average.
• Operate inside test environments that mirror a real sales tech stack, completing workflows across CRM, communication, and billing tools.
• Produce polished, customer-facing materials including pitches, slide decks, and summaries.
• Work with label types including evaluation ratings and text-generation tasks applied to sales documents and workflows.

Requirements

Candidates must bring deep, practical enterprise sales experience and strong technical familiarity with the standard enterprise stack.

• 10+ years of hands-on enterprise sales experience with a quota-carrying background.
• Proven track record of meeting or exceeding sales quotas.
• Day-to-day fluency with the standard enterprise stack: Salesforce, Jira, Confluence, Google Workspace, and Microsoft Office.
• Deep CRM administration, sales process management, pipeline tracking, and data-driven reporting skills.
• Strong writing ability to turn complex situations into clear, professional customer-facing artifacts.

Helpful background (preferred)

The following experience is not required but will make you a stronger candidate and help you contribute faster on complex evaluation tasks.

• Experience working within or alongside a two-sided, AI-powered B2B SaaS creator marketplace.
• Familiarity with outcome-based campaigns and troubleshooting across a connected sales/tech stack.

How this engagement works & next steps

Apply through OpenTrain to be considered. OpenTrain manages hiring and contracting for this project and will provide details about onboarding and the evaluation process to selected candidates.

Selected applicants can expect role-specific tasks that demonstrate expertise (sample evaluations or writing exercises) before contracting begins. This work is remote, US-only, and paid at the stated hourly rate.

• Languages required: English (fluent)
• Data type: Document-based tasks (evaluation ratings and text generation)
• Contractor status: You will be engaged as a contractor; schedule flexibility within a 20+ hrs/week commitment