Account Executive (Enterprise)

About WorkWhile WorkWhile is on a mission to help workers earn a better living and live better lives. 83 million Americans work hourly jobs, often with unpredictable schedules that pay close to minimum wage and offer limited benefits, leading to financial instability. WorkWhile identifies the best hourly workers and matches them with shifts that fit their skills, location, and life. Businesses get access to a quality workforce, while workers get stable income and unmatched benefits, including next day pay, free telehealth services, and financial services. We have the audacious goal to align incentives and solve inefficiencies in the labor market, disrupting the $650 billion staffing and recruiting market. Backed by Khosla Ventures and recognized by the Inc. 5000 for 10x growth, WorkWhile is reshaping the future of work. Role Summary We are looking for a high-performing Enterprise Account Executive to drive new business and strategic expansion within large, complex organizations. This role focuses on selling to enterprise-scale customers with multi-stakeholder environments, extended sales cycles, and significant revenue potential. You will leverage consultative selling, deep relationship building, and cross-functional alignment to exceed quota and contribute meaningfully to WorkWhile’s growth. Key Responsibilities 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. What You Bring 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). Compensation & 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.