This role is for one of our clientsCompensation: $60-$90 per hourA 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. Who We're Looking For 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. Nice to HaveExperience 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
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.
Requirements
Key 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.
Who We're Looking For
- 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.
Nice to Have
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 Opportunity
We 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
At Weekday (backed by YC; also Product Hunt #1 product of the day), we are building the next frontier in hiring. We have built the largest database of white collar talent in India and have built outreach tools on top of it to generate highest response rates.
At Weekday (backed by YC; also Product Hunt #1 product of the day), we are building the next frontier in hiring. We have built the largest database of white collar talent in India and have built outreach tools on top of it to generate highest response rates.
