[Hiring] Enterprise Sales Domain Expert @Weekday AI

Role Description

• 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
  • 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.

Qualifications

• 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
  • Customer relationship management
• Hands-on experience using enterprise sales tools such as:
  • Salesforce
  • Jira
  • Confluence
  • Google Workspace
  • 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.

Requirements

• 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.

Engagement Details

• 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.

Equal Opportunity

We are committed to creating an inclusive workplace and welcome applications from qualified professionals regardless of legally protected characteristics. Reasonable accommodations are available throughout the application and engagement process upon request.