Enterprise Account Executive - Hospitality

WorkWhile; San Francisco, Northern (CA, KY); Hybrid; USD 120,000 - 190,000; Full time

Benefits offered by this job

Competitive base salary

Commission with unlimited upside

Equity in a high-growth company

In-person off-sites

Medical, dental & vision coverage

Unlimited PTO

401(k) with employer match

WFH stipend

Job summary

WorkWhile is seeking an Enterprise Account Executive - Hospitality to drive new business and strategic expansion within major hospitality networks and event operators. You will lead a high-impact sales cycle, navigate complex organizational structures, and build executive relationships to deliver scalable labor solutions.

The role emphasizes consultative selling, regional and national opportunities, and a track record of closing six-figure+ deals, with travel to key conferences and client sites

Qualifications

• 5–10+ years of B2B enterprise sales experience in hospitality, events, or contract food service.
• Proven track record of hitting targets and closing large, strategic deals.
• Deep understanding of hospitality & event logistics and workforce impact on guest experience.
• Ability to navigate complex corporate structures and executive stakeholders.
• Proven experience with CRM tools and MEDDPICC/Challenger selling methodologies.

Responsibilities

• Drive the full sales cycle from prospecting to close with enterprise hospitality and event targets.
• Develop strategic account plans to penetrate and expand within large operators and venues.
• Navigate multi-department buy-ins to secure consensus and funding.
• Articulate labor solutions and ROI to CFOs and COOs in executive discussions.
• Maintain a robust pipeline with accurate forecasting for multi-city rollouts.

Skills

B2B enterprise sales

Consultative selling

Executive relationship building

Sales pipeline management

Negotiation

Sales leadership

Tools

Salesforce

MEDDPICC

Challenger

Strategic Selling

Job description

About WorkWhile

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 Summary

We 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 Responsibilities

• Drive 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.

What You Bring

• 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 + Commission (unlimited upside!) + 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!