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 tele-health 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 hiring a Mid-Market Account Executive to drive new business and expansion revenue within the mid-market segment, typically companies with ~$10M–$1B in annual revenue requiring shorter-to-moderate sales cycles. You’ll execute a consultative sales approach to uncover needs, demonstrate value, and close business while building a robust pipeline.
Key Responsibilities
Execute full sales cycle from prospecting and qualification through proposal, negotiation, and close for mid-market accounts. This is a hunter role.
Strategic and creative thinking that enables you to understand industry and customer trends and apply those insights to deliver business results
Generate and manage a healthy pipeline through outbound outreach, trade show/conference attendance, and strategic engagement.
Conduct discovery calls, tailored demos, and articulate WorkWhile’s value and product differentiators against competitors.
Build strong relationships with decision-makers (procurement/talent acquisition, operations, finance) and act as a trusted advisor.
Collaborate with internal cross-functional teams (sales, operations, finance) to ensure smooth onboarding and long-term satisfaction.
Provide accurate forecasting, pipeline metrics, and deal progression reporting.
What You Bring
3-6+ years of quota-carrying sales experience, preferably in SaaS, staffing/HR tech, or marketplace products.
Proven ability to close deals in the mid-market segment with a blend of consultative and transactional selling.
Solid communication skills and experience presenting to mid-level executives.
Comfortable balancing speed and strategy; agile in managing moderate sales cycles.
Compensation & Benefits
Competitive base salary + commission with clear OTE upside.
Equity
Full benefits package: medical/dental/vision, 401(k) with match, flexible time off, remote/hybrid options, and more.
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What We Do
WorkWhile is an AI-powered next generation labor platform that helps businesses in light industrial, hospitality, and events achieve over 90% fill rates and reduce no-shows through AI and predictive machine learning. We ensure seamless shift execution with trained, on-demand workers supported by on-site leads, real-time performance monitoring, and a robust accountability system. Our worker-first model boosts retention through benefits like next-day pay, telehealth, and free upskilling, while our platform delivers real-time analytics and dedicated support for every client. By combining flexibility, reliability, and deep insights, WorkWhile helps businesses scale efficiently and stay competitive.
Why Work With Us
WorkWhile is a technology platform with product and engineering at its core. Founded by alumni from Google, Meta, Yahoo, and Airbnb, continuous innovation is our strategy. We are an AI-native company that doesn’t just adopt new technologies, we operationalize them at scale to solve real business challenges.
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WorkWhile Offices
Hybrid Workspace
Employees engage in a combination of remote and on-site work.
Our hybrid policy allows workers to work flexibly - either in person in one of our four hubs (San Francisco HQ, New York, Seattle, Toronto), or remote. We encourage employees coming in person to come 2-3x per week.
