Enterprise Sales Domain Expert

Weekday 1; United States; Remote; USD 83,000 - 124,000; Full time

Job summary

Weekday 1 is seeking an experienced Enterprise Sales Domain Expert to evaluate AI-driven sales workflows and establish benchmarks in enterprise sales. You will bring hands‑on selling experience to identify gaps, craft reference examples, and help define what excellent enterprise selling looks like.

This full‑time, remote role is open to candidates within the United States. The position requires deep knowledge of the complete sales lifecycle, quota attainment, and familiarity with tools like

Qualifications

• Approximately 10 years of hands‑on enterprise sales experience.
• Proven history of meeting or exceeding sales quotas.
• Strong knowledge of enterprise prospecting, discovery, qualification, deal management, and forecasting.

Responsibilities

• Evaluate AI-generated sales workflows for alignment with enterprise selling practices.
• Develop expert benchmarks and end-to-end sales scenarios in sandbox environments.
• Refine scoring rubrics and evaluate AI performance against enterprise standards.
• Create polished sales artifacts including pitches, proposals, and executive summaries.
• Provide structured, evidence-based feedback on AI outputs.

Skills

Enterprise sales

Quota attainment

CRM proficiency

Sales strategy

Stakeholder management

Tools

Salesforce

Jira

Confluence

Google Workspace

Microsoft Office

Slack

HubSpot

Notion

Aircall

Stripe

Intercom

Zoho

Microsoft Teams

Job description

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