Enterprise Sales Domain Expert

Weekday AI

1d • $60 - $90 • Remote

About The Position

This role involves evaluating AI-generated enterprise sales workflows to ensure they align with real-world best practices. The expert will identify gaps and inaccuracies in AI outputs, provide actionable feedback, and develop high-quality reference examples for various sales activities. The position requires performing end-to-end sales workflows in simulated environments and producing customer-facing sales materials. Collaboration with research teams and other subject matter experts is key to improving AI reasoning and decision-making in sales use cases.

Requirements

• Approximately 10 years of professional experience in enterprise sales with extensive exposure to the complete sales lifecycle.
• Proven history of consistently achieving or exceeding sales quotas.
• Experience as an individual contributor, sales manager, director, or executive overseeing enterprise sales organizations.
• Strong expertise in CRM administration, sales operations, pipeline management, forecasting, sales reporting, and customer relationship management.
• Hands-on experience using enterprise sales tools such as Salesforce, Jira, Confluence, Google Workspace, and Microsoft Office.
• Comfortable working with additional collaboration and sales platforms including Slack, HubSpot, Notion, Aircall, Stripe, Intercom, Zoho, and Microsoft Teams.
• Excellent written communication skills with the ability to produce executive-level customer-facing documents.
• Strong analytical thinking and attention to detail.

Nice To Haves

• Experience working within AI-powered B2B SaaS organizations, digital marketplaces, or performance-driven enterprise sales environments.
• Familiarity with outcome-based sales campaigns and KPI tracking, including metrics such as customer engagement, conversions, installations, and sign-ups.
• Experience coordinating workflows across integrated business platforms such as Zoho CRM, Freshdesk, Jira, Confluence, Microsoft Teams, and Google Workspace.
• Ability to quickly adapt to new enterprise software platforms and evolving business workflows.

Responsibilities

• Evaluate multi-step enterprise sales workflows and determine whether AI-generated outputs reflect real-world best practices.
• Identify gaps, inaccuracies, and missed opportunities in AI-generated sales processes while providing clear, actionable feedback.
• Develop high-quality reference ("gold standard") examples covering activities such as prospecting, lead qualification, pipeline management, CRM maintenance, customer communications, sales reporting, and proposal and presentation development.
• Help design and refine evaluation frameworks and scoring rubrics that accurately measure AI performance in enterprise sales scenarios.
• Perform end-to-end sales workflows within simulated enterprise environments using modern sales and productivity platforms.
• Produce polished, customer-facing sales materials including presentations, proposals, executive summaries, and account documentation.
• Collaborate with research teams and fellow subject matter experts to improve AI reasoning and decision-making across sales use cases.

Benefits

• Full-time remote opportunity within the United States.
• Work closely with AI researchers and domain experts to improve enterprise sales intelligence.
• Contribute to projects that directly influence the development of next-generation AI systems.
• Long-term engagement based on project requirements and performance.

What This Job Offers

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