Enterprise Sales Domain Expert | $60-$90/hr Remote
Overview
A leading AI research lab is teaching its models to navigate the multi-step, judgment-heavy workflows of enterprise sales. They need seasoned sellers who have carried quotas to act as the benchmark — auditing AI outputs, creating reference examples, and setting the quality standards the model learns from. In this role, your real-world sales expertise directly shapes how cutting-edge AI handles prospecting, pipeline management, and customer-facing materials.
What You'll Do5
- 1Evaluate AI performance on complex enterprise sales workflows by spotting errors and explaining why a real seller would handle things differently.
- 2Create golden reference examples by working end-to-end sales tasks — from prospecting and pipeline tracking to CRM hygiene and client documents — giving the model high-quality learning data.
- 3Refine scoring rubrics that measure AI output quality, ensuring they capture what separates average selling from expert-level execution.
- 4Simulate real sales environments using test versions of CRM, communication, and billing tools to complete and assess workflows.
- 5Produce polished, senior-level artifacts like pitch decks, executive summaries, and customer-ready materials that reflect the caliber of a top enterprise seller.
Requirements4
- 1Roughly 10 years of hands-on enterprise sales experience with a demonstrated history of exceeding quota — you can talk specifics about targets and results.
- 2Deep fluency with standard enterprise tools (Salesforce, Jira, Confluence, Google Workspace, Microsoft Office) and comfort picking up platforms like Slack, HubSpot, Notion, Aircall, Stripe, Intercom, Zoho, and Microsoft Teams.
- 3Solid CRM administration and sales process management skills, including pipeline tracking, data-driven reporting, and workflow optimization.
- 4Strong writing and attention to detail — you can turn complex situations into clear, professional, customer-facing documents.
Who Should Apply
This role is built for experienced enterprise sellers who have carried quotas and know the full sales cycle inside out. Whether you're an individual contributor, a sales manager, or a VP running a regional team, if you can speak to specific quota achievements and are comfortable using a modern sales stack to produce high-quality artifacts, you're the ideal candidate. Experience with AI-powered platforms or two-sided marketplaces is a plus, but the core requirement is deep, practical sales expertise.
Salary Insight
Compensation is $60.00 - $90.00 per hour, paid as a W-2 employee through Cincinnatus LLC.
Application Tip
In your application, include a concrete example of a complex sales workflow you've managed — such as a multi-stakeholder deal or a pipeline cleanup — and explain how you would evaluate an AI's attempt to replicate that process. This demonstrates both your domain expertise and your ability to think critically about model performance.
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