Jobs · Sales

Enterprise Sales Domain Expert

Weekday AI (YC W21) · United States · 1 wk ago
RemoteRemoteSales$60–$90/hrPart-time

Key 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, Proposal and presentation development
  • 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

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, 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

Qualifications

  • 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

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