Account Executive – Enterprise

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🕒 March 13

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WorkWhile

WebsiteLinkedInAll Job Openings

51 - 200 employees

👥 HR Tech

☁️ SaaS

🤖 Artificial Intelligence

💰 $23M Series B - WorkWhile on 2025-06

HR Tech • SaaS • Artificial Intelligence

WorkWhile is an AI-powered labor and workforce-management platform that connects businesses with vetted, certified frontline workers for on-demand, temporary, and long-term assignments. The platform provides a full-stack, SaaS workforce solution—matching and scheduling talent across industries like warehousing, logistics, manufacturing, hospitality, facilities, and retail—while offering features such as background checks, certification support, next-day pay, a worker app, and machine-learning driven real-time labor management and insights. WorkWhile positions itself as a single source of truth for dynamic staffing needs, enabling businesses to scale flexibly with transparent pricing and data-driven staffing decisions.

📋 Description

• Lead full sales cycle for enterprise targets: prospecting, discovery, solution positioning, negotiation, and close. This is a hunter role. • Develop strategic account plans to penetrate and expand within Fortune 500 / national accounts. • Drive consensus and alignment across multiple departments (ops, finance, procurement) at target customers. • Articulate WorkWhile’s value proposition in enterprise labor strategy, workforce analytics, and flexible staffing solutions. • Build and maintain a robust pipeline with enterprise opportunities and accurate sales forecasting. • Collaborate internally with sales, finance, operations and product stakeholders to deliver tailored enterprise proposals and proofs of concept. • Represent WorkWhile at industry events and executive meetings.

🎯 Requirements

• 5-10+ years of B2B enterprise sales experience with a track record of hitting targets and closing large, strategic deals. • Demonstrated ability to navigate complex approval processes and multiple executive stakeholders. • Strong consultative selling skills with executive presence and financial acumen. • History of exceeding quota, closing six-figure+ deals, and driving long-term customer value. • Experience with CRM tools (Salesforce) and enterprise sales methodologies (e.g., MEDDPICC).

🏖️ Benefits

• Competitive base salary + commission with clear OTE upside. • Equity • Comprehensive benefits including medical, dental, vision, 401(k) match, flexible time off, and remote/hybrid work options.