This role is for one of our clients
Compensation: $60-$90 per hour
A leading AI research organization is developing advanced AI systems capable of performing complex, real-world enterprise sales workflows. To ensure these systems reflect authentic sales practices, we are seeking experienced enterprise sales professionals to provide expert judgment, create high-quality reference examples, and establish evaluation standards.
As an Enterprise Sales Domain Expert, you will bring hands-on selling experience to evaluate AI-driven sales workflows, identify gaps in reasoning and execution, develop benchmark examples, and help define what excellent enterprise selling looks like. This role is designed for accomplished, quota-carrying sales professionals and experienced sales leaders with strong knowledge of enterprise sales processes.
This is a full-time role, fully remote within the United States.
RequirementsKey Responsibilities
- Evaluate Sales Workflows: Review multi-step enterprise sales workflows and assess whether AI-generated actions, decisions, and outputs reflect the practices of a high-performing sales professional.
- Develop Expert Benchmarks: Execute realistic sales scenarios end-to-end, including prospecting, pipeline management, CRM activities, reporting, and customer communications, to create high-quality reference examples.
- Refine Evaluation Criteria: Test, improve, and calibrate scoring rubrics to ensure AI performance is evaluated against meaningful enterprise sales standards.
- Work in Sales Environments: Navigate realistic sandbox environments that replicate enterprise sales technology stacks, including CRM, communication, collaboration, and billing platforms.
- Create Sales Artifacts: Develop polished, customer-ready materials such as sales pitches, presentations, account summaries, proposals, and executive communications.
- Provide Expert Feedback: Identify weaknesses, inconsistencies, and missed opportunities in AI-generated sales work and clearly explain how the output could be improved.
- Apply Professional Judgment: Distinguish between technically plausible sales activity and approaches that would genuinely work with enterprise buyers.
- Approximately 10 years of hands-on enterprise sales experience, with strong knowledge of the complete sales lifecycle.
- Demonstrated history of meeting or exceeding sales quotas, with the ability to discuss measurable performance outcomes.
- Open to experienced quota-carrying Individual Contributors, Sales Managers, Directors, and VPs who have substantial hands-on sales expertise.
- Strong understanding of enterprise prospecting, discovery, qualification, deal management, pipeline development, forecasting, and account strategy.
- Day-to-day familiarity with enterprise tools such as Salesforce, Jira, Confluence, Google Workspace, and Microsoft Office.
- Comfortable learning and working with platforms such as Slack, HubSpot, Notion, Aircall, Stripe, Intercom, Zoho, and Microsoft Teams.
- Strong experience with CRM administration, sales process management, pipeline tracking, reporting, and sales operations workflows.
- Excellent written communication and strong attention to detail, with the ability to transform complex sales situations into polished, professional deliverables.
- Comfortable evaluating AI-generated work and providing structured, evidence-based feedback.
Experience working with or alongside AI-powered B2B SaaS platforms, two-sided marketplaces, or creator/economy technology businesses is a plus.
Additional experience managing outcome-based campaigns, performance targets, real-time engagement metrics, or interconnected sales and support technology stacks is also valuable.
Equal Employment OpportunityWe are committed to providing equal employment opportunities to all qualified applicants. Employment decisions are made without regard to legally protected characteristics, and reasonable accommodations are available to qualified individuals with disabilities and disabled veterans throughout the application process.
Engagement Details- Role: Enterprise Sales Domain Expert
- Employment Type: Full-Time
- Work Arrangement: Fully Remote
- Location: United States
- Focus: Enterprise Sales, AI Evaluation & Training
- Experience: Approximately 10 years of enterprise sales experience
- Commitment: Full-Time
- Engagement: Opportunity to contribute to advanced AI research and evaluation initiatives
- Work Style: Independent, detail-oriented, and comfortable working with evolving workflows and evaluation standards
Skills Required
- Approximately 10 years of hands-on enterprise sales experience
- Demonstrated history of meeting or exceeding sales quotas with measurable outcomes
- Strong knowledge of the complete sales lifecycle: prospecting, discovery, qualification, deal management, pipeline development, forecasting, and account strategy
- Day-to-day familiarity with enterprise tools: Salesforce, Jira, Confluence, Google Workspace, and Microsoft Office
- Comfortable learning and working with platforms such as Slack, HubSpot, Notion, Aircall, Stripe, Intercom, Zoho, and Microsoft Teams
- Strong experience with CRM administration, sales process management, pipeline tracking, reporting, and sales operations workflows
- Excellent written communication and strong attention to detail; ability to produce polished, professional deliverables
- Comfortable evaluating AI-generated work and providing structured, evidence-based feedback
- Experience working with or alongside AI-powered B2B SaaS platforms, two-sided marketplaces, or creator/economy businesses
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.
