Weekday (YC W21) logo
Weekday (YC W21)

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Enterprise Sales Domain Expert

SalesSalesPart TimeRemoteLeadTeam 11-50Since 2021H1B No SponsorCompany SiteLinkedIn

Location

United States

Posted

10 hours ago

Salary

$60 - $90 / hour

Seniority

Lead

10 yrs expEnglish

Job Description

Enterprise Sales Domain Expert

Weekday (YC W21)

• 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.

Job 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.
  • 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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