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