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    Enterprise Account Executive - Hospitality

    WorkWhile

    🇺🇸 USA
    Remote
    ["Full-Time"]
    SaaS
    Base + Commission
    See your match score
    Posted Today
    Job Type

    ["Full-Time"]

    Work Type

    Remote

    Vertical

    SaaS

    Source

    jobicy

    About this role

    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, an

    Selling Motion

    Sales Cycle

    Enterprise

    6–18 month cycles, complex multi-stakeholder deals

    Prospecting

    Outbound-Heavy

    Self-sourced pipeline via cold outreach

    Buyer Persona

    C-Suite

    Selling to executive decision-makers

    Territory

    Vertical-Specific

    Focused on a single industry vertical

    Requirements at a Glance

    Bachelor's Degree·Required
    Prospecting·Required skill
    Negotiation·Required skill
    Consultative Selling·Required skill

    Typical Day — Account Executive

    Stakeholder meetings3–5/week
    Executive presentations2–3/week
    Business cases & RFPs1–2/week
    Forecast & pipeline2×/week
    Champion coachingDaily

    Estimates based on role type and selling motion — actual may vary by company.

    SaaS — Interview Intel

    Typical Sales Cycle

    30–90 days (SMB) · 3–9 months (Mid-Market) · 6–18 months (Enterprise)

    Common Buyer Objections

    • "We're locked into a contract with [competitor]"
    • "We built something in-house already"
    • "We don't have budget until next quarter"
    • "Our team won't adopt another tool"

    Key Industry Metrics

    ARR / MRRNet Revenue Retention (NRR)CAC Payback PeriodLogo Churn vs Revenue ChurnACV (Avg Contract Value)Magic Number

    Hot Topics to Reference

    • • AI-native product disruption
    • • PLG vs sales-led motion debate
    • • Vertical SaaS consolidation
    • • Usage-based pricing models

    Use these insights to speak the buyer's language in interviews.

    Tags

    sales
    —

    Walk me through your discovery process.

    Template question
    —

    How do you handle a prospect who goes silent mid-deal?

    Template question
    —

    Tell me about your largest closed deal and the sales cycle.

    Template question
    —

    How do you build business cases for stakeholders?

    Template question
    —

    Describe a deal you lost and what you learned.

    Template question
    Research WorkWhile's product, recent news, and key competitors
    Prepare metrics: quota attainment %, average deal size, win rate
    Practice a 2-minute product demo pitch for a mock discovery call
    Research typical OTE splits for this role level and negotiate accordingly
    Prepare to discuss your home office setup and self-management discipline
    Review the job description and map your experience to each requirement
    Role Insights

    As an Account Executive with WorkWhile, you'll own the entire revenue pipeline and be measured on quota attainment.

    Expect to work with recurring revenue models where customer retention is as important as acquisition.

    This remote-friendly role provides geographic flexibility while maintaining access to a SaaS market.

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