About this role.
WorkWhile is hiring an Account Executive to drive strategic new-business sales and account expansion in the light industrial, hospitality, and retail sectors. The role owns the full sales cycle, including prospecting, qualification, stakeholder mapping, customer evaluation, closing, and expansion. Candidates need 3–5+ years of quota-carrying closing experience, enterprise-sales exposure, and a consistent record of exceeding quota. This is a US-remote, full-time role that partners closely with account management, operations, and sales development teams.
Role DNA
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Job Complexity
4/5Pace & Pressure
4/5Autonomy Level
4/5Communication Load
5/5Salary analysis
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Core skills
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Cover letter sample
Dear Hiring Team,
I am excited to apply for the Account Executive role at WorkWhile. My background in quota-carrying, consultative sales has prepared me to build executive relationships, navigate complex stakeholder groups, and close strategic new-business opportunities.
I am particularly drawn to WorkWhile's mission to create more stable, rewarding work for hourly professionals while helping businesses access dependable talent. I would welcome the opportunity to bring a customer-centric, data-informed approach to growing your presence across light industrial, hospitality, and retail accounts.
Thank you for your consideration. I look forward to discussing how I can contribute to WorkWhile's continued growth.
Sample interview questions
I segment the market by ideal customer profile, business need, buying complexity, and potential value. I research each account's workforce challenges, map likely decision-makers and influencers, then use tailored multichannel outreach to earn discovery conversations. I maintain disciplined pipeline hygiene and review conversion metrics regularly to improve the approach.
I begin by establishing the customer's business context and desired outcomes rather than leading with product features. I ask open-ended questions about current processes, operational constraints, workforce needs, decision criteria, and the consequences of inaction. I summarize the priorities back to the customer and connect the solution only to validated needs.
I create a stakeholder map that identifies champions, economic buyers, operational users, and potential blockers. I tailor the value narrative to each person's priorities while maintaining a shared business case tied to measurable outcomes. I also confirm the decision process, timeline, and next steps early so that consensus can be built deliberately.
I review the opportunity objectively to identify whether the issue was qualification, stakeholder coverage, urgency, competitive positioning, or execution. I seek feedback from the customer and internal partners, decide whether a recovery plan is realistic, and document the learning in my sales process. I then apply those insights to improve qualification and forecasting for future deals.
I provide a thorough handoff that includes customer goals, stakeholders, commitments, implementation risks, success measures, and expansion potential. I stay engaged during the early customer lifecycle to ensure expectations are met and to support executive alignment. Regular account reviews help identify growth opportunities while preserving a strong customer experience.
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 telehealth 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.
About the Role
WorkWhile is looking for an experienced Account Executive with a proven track record of success to join our rapidly growing team. This role is responsible for strategic new business sales and expansion. As an Account Executive you will manage all aspects of the sales process including prospecting, lead management, qualification, customer evaluation, closing new business, and expansion. This role will be focusing on the light industrial, hospitality, and retail verticals.
The ideal candidate must have an entrepreneurial mindset, a hunger for success, and a consultative customer-centric approach.
Demonstrate a strong business case for WorkWhile through a consultative and value-driven sales process
Establish a collaborative business relationship between WorkWhile and key decision makers within target accounts
Meet and exceed your goals through prospecting, qualifying, managing, and closing new sales opportunities
Partner with account management, operations, and sales development teams to drive revenue
About you
3-5+ years of sales experience in a quota carrying, closing role
Experience in enterprise sales.
A track record of success – consistently exceeding quota
Experiencing breaking down accounts to identify multiple decision makers
Strong presentation and communication skills with the ability to influence others over the phone/Zoom
Strategic and creative thinking that enables you to understand industry and customer trends and apply those insights to deliver business results
Benefits & Perks
Hybrid work culture with office hubs in SF, NY & Toronto
In-person company offsites
Medical, dental, & vision coverage
Flexible time off
401(k) with employer match
WFH stipend to support your home office needs
Target Hiring Range: $100K– $150k per year base salary
This range represents the good-faith estimate of the base salary/wage we reasonably expect to pay at the time of hire. Final offer amounts are determined by multiple factors, including experience, skills, and geography.
Additional Compensation:
Commission: This role is eligible for commission.
Equity: This position is eligible for [RSUs/Stock Options] as part of our long-term incentive program.
WorkWhile is an Equal Opportunity Employer. Women, minorities, individuals with disabilities and protected veterans are encouraged to apply. 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!
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