WorkWhile is on a mission to help workers earn a better living and live better lives. 83 million Americans work hourly jobs: the true backbone of the hospitality, catering, and event industries. These workers often face highly volatile schedules, sudden booking surges, and limited benefits.
WorkWhile identifies the best, most reliable hourly workers and matches them with shifts that fit their skills, location, and life. For high-volume catering companies, stadium and venue operators, corporate food service providers, and large-scale event producers, we provide instant access to a vetted, high-quality workforce to seamlessly scale up for major events and peak periods. For workers, we provide stable income and unmatched benefits, including next-day pay, free telehealth services, upskilling, and financial wellness tools.
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 in hospitality and live events.
Role SummaryWe are looking for a high-performing Enterprise Account Executive – Hospitality to drive new business and strategic expansion within catering conglomerates, national contract food service providers, sports and entertainment venue operators, and premier event management groups.
This role focuses on selling flexible labor solutions to enterprise-scale organizations with multi-stakeholder environments, extended sales cycles, and significant volume requirements. You will leverage your expertise in the events and food service sectors, consultative selling, and executive relationship-building to transform how major hospitality brands staff their operations, helping you exceed quota and meaningfully contribute to WorkWhile’s growth.
Key ResponsibilitiesDrive the Full Sales Cycle: Prospect, discover, position solutions, negotiate, and close enterprise hospitality and event targets. This is a hunter role designed for someone who loves opening doors with major national operators.
Target High-Volume Accounts: Develop strategic account plans to penetrate and expand within corporate food service operators, national catering networks, and large sports/entertainment venues.
Navigate Complex Buy-ins: Drive consensus and alignment across multiple departments, such as Corporate Operations, VP of Talent Acquisition, Procurement, and regional Event/Culinary Directors.
Position Labor Strategy: Articulate WorkWhile’s value proposition in solving distinct hospitality pain points, including hyper-seasonal staffing volatility, last-minute event cancellations, variable labor costs, while maintaining strict service standards for our Partners.
Manage a Robust Pipeline: Build and maintain an active pipeline of enterprise food service and event opportunities with highly accurate sales forecasting.
Collaborate Internally: Work closely with WorkWhile’s operations, finance, and product teams to deliver tailored workforce proposals and proofs of concept (POCs) for major multi-city rollouts or high-profile events.
Represent the Brand: Act as the face of WorkWhile at key hospitality and event industry conferences, trade shows, and executive meetings. Willingness to travel when needed.
5–10+ years of B2B enterprise sales experience, with a proven track record of hitting targets and closing large, strategic deals within the contract food service, event management, university, catering, or venue operations sectors.
Deep Hospitality & Event IQ: A profound understanding of the logistics behind large-scale catering, stadium operations, and corporate dining, and how workforce reliability directly impacts guest experience and margin.
Navigational Excellence: Demonstrated ability to navigate complex corporate structures, multi-unit concessionaires, and multiple executive stakeholders.
Consultative Selling Mastery: Strong executive presence, financial acumen, and the ability to turn abstract labor data into a compelling ROI story for a CFO or Chief Operating Officer.
Proven Performance: A history of exceeding quota, closing six-figure+ deals, and driving long-term customer lifetime value.
Modern Sales Tech Stack: Experience with CRM tools (Salesforce) and enterprise sales methodologies (e.g., MEDDPICC, Challenger, or Strategic Selling).
Compensation & Benefits
Competitive base salary + equity in a high-growth, venture-backed company
In-person company off-sites
Medical, dental & vision coverage
Unlimited PTO
401(k) with employer match
WFH stipend to support your home office setup
WorkWhile has a diverse, mission-driven, and supportive culture—we look for people who want to take ownership, are energized by ambiguity, and strive to make a lasting impact. If this resonates with you, we’d love to chat!
WorkWhile Toronto, Ontario, CAN Office
Toronto, ON, Canada
