This role is for one of our clients
Compensation: $60-$90 per hour
RequirementsKey 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
- 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.
- 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.
- 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.
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.
Skills Required
- Approximately 10 years of professional experience in enterprise sales
- Proven history of consistently achieving or exceeding sales quotas
- Experience as individual contributor, sales manager, director, or executive overseeing enterprise sales organizations
- Expertise in CRM administration
- Expertise in sales operations and pipeline management
- Experience with forecasting and sales reporting
- Customer relationship management experience
- Hands-on experience with Salesforce
- Hands-on experience with Jira and Confluence
- Proficiency with Google Workspace and Microsoft Office
- Familiarity/comfort using Slack, HubSpot, Notion, Aircall, Stripe, Intercom, Zoho, and Microsoft Teams
- Excellent written communication skills for executive-level customer-facing documents
- Strong analytical thinking and attention to detail
- Experience working within AI-powered B2B SaaS, digital marketplaces, or performance-driven enterprise sales environments
- Familiarity with outcome-based sales campaigns and KPI tracking (engagement, conversions, installations, sign-ups)
- Experience coordinating workflows across integrated business platforms (e.g., Zoho CRM, Freshdesk, Jira, Confluence, Microsoft Teams, Google Workspace)
- Ability to quickly adapt to new enterprise software platforms and evolving workflows
What We Do
Weekday is an AI-powered recruitment platform that helps startups hire top-tier engineering and product talent. By leveraging a massive database of white-collar professionals and advanced outreach tools, the company streamlines the hiring process through automated sourcing, AI-driven resume screening, and white-glove contingency services. Their mission is to modernize recruitment by enabling companies to discover and engage passive candidates efficiently, ensuring high-quality hires for critical roles.

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