Enterprise Sales Domain Expert

Weekday AI

13h • $60 - $90 • Remote

About The Position

A leading AI research organization is developing advanced AI systems capable of performing complex, real-world enterprise sales workflows. To ensure these systems reflect authentic sales practices, we are seeking experienced enterprise sales professionals to provide expert judgment, create high-quality reference examples, and establish evaluation standards. As an Enterprise Sales Domain Expert, you will bring hands-on selling experience to evaluate AI-driven sales workflows, identify gaps in reasoning and execution, develop benchmark examples, and help define what excellent enterprise selling looks like. This role is designed for accomplished, quota-carrying sales professionals and experienced sales leaders with strong knowledge of enterprise sales processes. This is a full-time role, fully remote within the United States.

Requirements

• Approximately 10 years of hands-on enterprise sales experience, with strong knowledge of the complete sales lifecycle.
• Demonstrated history of meeting or exceeding sales quotas, with the ability to discuss measurable performance outcomes.
• Open to experienced quota-carrying Individual Contributors, Sales Managers, Directors, and VPs who have substantial hands-on sales expertise.
• Strong understanding of enterprise prospecting, discovery, qualification, deal management, pipeline development, forecasting, and account strategy.
• Day-to-day familiarity with enterprise tools such as Salesforce, Jira, Confluence, Google Workspace, and Microsoft Office.
• Comfortable learning and working with platforms such as Slack, HubSpot, Notion, Aircall, Stripe, Intercom, Zoho, and Microsoft Teams.
• Strong experience with CRM administration, sales process management, pipeline tracking, reporting, and sales operations workflows.
• Excellent written communication and strong attention to detail, with the ability to transform complex sales situations into polished, professional deliverables.
• Comfortable evaluating AI-generated work and providing structured, evidence-based feedback.

Nice To Haves

• Experience working with or alongside AI-powered B2B SaaS platforms, two-sided marketplaces, or creator/economy technology businesses is a plus.
• Additional experience managing outcome-based campaigns, performance targets, real-time engagement metrics, or interconnected sales and support technology stacks is also valuable.

Responsibilities

• Evaluate Sales Workflows: Review multi-step enterprise sales workflows and assess whether AI-generated actions, decisions, and outputs reflect the practices of a high-performing sales professional.
• Develop Expert Benchmarks: Execute realistic sales scenarios end-to-end, including prospecting, pipeline management, CRM activities, reporting, and customer communications, to create high-quality reference examples.
• Refine Evaluation Criteria: Test, improve, and calibrate scoring rubrics to ensure AI performance is evaluated against meaningful enterprise sales standards.
• Work in Sales Environments: Navigate realistic sandbox environments that replicate enterprise sales technology stacks, including CRM, communication, collaboration, and billing platforms.
• Create Sales Artifacts: Develop polished, customer-ready materials such as sales pitches, presentations, account summaries, proposals, and executive communications.
• Provide Expert Feedback: Identify weaknesses, inconsistencies, and missed opportunities in AI-generated sales work and clearly explain how the output could be improved.
• Apply Professional Judgment: Distinguish between technically plausible sales activity and approaches that would genuinely work with enterprise buyers.

Benefits

• Equal employment opportunities to all qualified applicants.
• Employment decisions are made without regard to legally protected characteristics.
• Reasonable accommodations are available to qualified individuals with disabilities and disabled veterans throughout the application process.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed