Account Executive (Mid-Market)

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.