Enterprise Sales Domain Expert

atWeekday (YC W21)RemoteUS flagUnited StatesFull-timeSalesSeniorLead$60 – $90/hour

Posted Aug 14

This is a fully remote position, open to applicants in United States.

📋 Description

• Evaluate multi-step enterprise sales workflows to determine if AI-generated actions, decisions, and outputs align with high-performing sales practices.

• Implement realistic end-to-end sales scenarios, which encompass prospecting, pipeline management, CRM activities, reporting, and customer interactions to develop reference examples.

• Test, enhance, and calibrate scoring rubrics for assessing AI performance against enterprise sales benchmarks.

• Navigate sandbox environments that mimic enterprise sales technology stacks, including CRM, communication, collaboration, and billing platforms.

• Develop customer-ready sales pitches, presentations, account summaries, proposals, and executive communications.

• Identify weaknesses, inconsistencies, and missed opportunities in AI-generated sales outputs and propose improvements.

• Differentiate technically feasible sales activities from strategies that genuinely resonate with enterprise buyers.

• Participate in advanced AI research and evaluation initiatives.


⛳️ Requirements

• Around 10 years of direct experience in enterprise sales.

• Comprehensive understanding of the entire sales lifecycle.

• Proven track record of meeting or surpassing sales quotas and the ability to discuss measurable performance outcomes.

• Open to quota-carrying Individual Contributors, Sales Managers, Directors, and VPs with significant hands-on sales experience.

• Strong grasp of enterprise prospecting, discovery, qualification, deal management, pipeline development, forecasting, and account strategy.

• Daily familiarity with Salesforce, Jira, Confluence, Google Workspace, and Microsoft Office.

• Willingness to learn and work with Slack, HubSpot, Notion, Aircall, Stripe, Intercom, Zoho, and Microsoft Teams.

• Extensive experience in CRM administration, sales process management, pipeline tracking, reporting, and sales operations workflows.

• Exceptional written communication skills and a keen attention to detail.

• Capability to translate complex sales scenarios into polished, professional deliverables.

• Comfortable assessing AI-generated work and providing structured, evidence-based feedback.

• Experience with AI-driven B2B SaaS platforms, two-sided marketplaces, or creator/economy technology ventures is advantageous.

• Background in managing outcome-based campaigns, performance targets, real-time engagement metrics, or interconnected sales and support technology stacks is beneficial.


🏝️ Benefits

• Fully remote position within the United States.

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