Remote Enterprise Sales Domain Expert - AI-Powered

Weekday AI; United States; Remote; USD 171,924,000 - 257,887,000; Full time

Job summary

Weekday AI is seeking a seasoned enterprise sales professional for a remote, US-wide engagement. You will evaluate AI-generated sales workflows, identify gaps, and craft gold-standard examples across prospecting, pipeline, CRM, and reporting.

You will design evaluation rubrics, run end-to-end sales simulations, and produce executive-facing materials. This long-term role rewards deep domain expertise in enterprise SaaS sales and CRM platforms.

Qualifications

• Approximately 10 years of professional experience in enterprise sales across the full lifecycle.
• Proven history of consistently meeting or exceeding sales quotas.
• Experience as an individual contributor, sales manager, director, or executive overseeing enterprise sales teams.
• Strong expertise in CRM administration, sales operations, forecasting, and sales reporting.

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 reference examples covering Prospecting, Lead qualification, Pipeline management, CRM maintenance, Customer communications, Sales reporting, and Proposal development.
• Help design evaluation frameworks and scoring rubrics to measure AI performance in enterprise sales scenarios.
• Perform end-to-end sales workflows within simulated enterprise environments using modern sales platforms.
• Produce polished, customer-facing sales materials including presentations, proposals, executive summaries, and account documentation.
• Collaborate with research teams to improve AI reasoning and decision-making across sales use cases.

Skills

Enterprise sales

CRM administration

Sales operations

Forecasting

Sales reporting

Lead qualification

Tools

Salesforce

Jira

Confluence

Google Workspace

Microsoft Office

Slack

HubSpot

Notion

Aircall

Stripe

Intercom

Zoho

Microsoft Teams

Job description

Weekday AI is seeking a seasoned enterprise sales professional for a remote, US-wide engagement. You will evaluate AI-generated sales workflows, identify gaps, and craft gold-standard examples across prospecting, pipeline, CRM, and reporting.

You will design evaluation rubrics, run end-to-end sales simulations, and produce executive-facing materials. This long-term role rewards deep domain expertise in enterprise SaaS sales and CRM platforms.