Enterprise Sales Domain Expert

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Weekday (YC W21)

WebsiteLinkedInAll Job Openings

11 - 50 employees

Founded 2021

💼 Consulting

👥 HR Tech

☁️ SaaS

Consulting • HR Tech • SaaS

Weekday is a modern recruitment platform that combines AI technologies with a vast database of potential candidates, aiming to streamline the hiring process for companies in India. They offer various services, including a proactive outreach approach that helps employers connect with top talent, as well as tools for candidates to easily apply for jobs. Weekday's emphasis on candidate engagement through multiple channels, including email, WhatsApp, and phone calls, sets it apart in the competitive landscape of recruitment agencies.

📋 Description

• Review multi-step enterprise sales workflows and assess whether AI-generated actions, decisions, and outputs reflect high-performing sales practices • Execute realistic end-to-end sales scenarios, including prospecting, pipeline management, CRM activities, reporting, and customer communications, to create reference examples • Test, improve, and calibrate scoring rubrics for evaluating AI performance against enterprise sales standards • Navigate sandbox environments replicating enterprise sales technology stacks, including CRM, communication, collaboration, and billing platforms • Create customer-ready sales pitches, presentations, account summaries, proposals, and executive communications • Identify weaknesses, inconsistencies, and missed opportunities in AI-generated sales work and explain improvements • Distinguish technically plausible sales activity from approaches that genuinely work with enterprise buyers • Contribute to advanced AI research and evaluation initiatives

🎯 Requirements

• Approximately 10 years of hands-on enterprise sales experience • Strong knowledge of the complete sales lifecycle • Demonstrated history of meeting or exceeding sales quotas and ability to discuss measurable performance outcomes • Open to quota-carrying Individual Contributors, Sales Managers, Directors, and VPs with 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 Salesforce, Jira, Confluence, Google Workspace, and Microsoft Office • Comfortable learning and working with 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 transform complex sales situations into polished, professional deliverables • Comfortable evaluating AI-generated work and providing structured, evidence-based feedback • Experience with AI-powered B2B SaaS platforms, two-sided marketplaces, or creator/economy technology businesses is a plus • Experience managing outcome-based campaigns, performance targets, real-time engagement metrics, or interconnected sales and support technology stacks is valuable • Fully remote within the United States