Location: Remote (US), with ability to travel up to 25% of time
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.
About the Role
WorkWhile is looking for a dynamic Pod Lead to own the Enterprise Retail segment. This is a "Vertical CEO" role where you own the entire customer lifecycle. You will lead a specialized unit (Pod) tasked with aggressive new business acquisition (Growth), world-class operational delivery (Retention), and strategic account scaling (Expansion).
Your mandate: establish WorkWhile as the primary flexible workforce platform for the world’s largest big-box retailers, grocery chains, omni-channel operators and warehousing and logistics companies. You will lead a dedicated POD of Enterprise Account Executives and Account Managers, acting as the strategic architect for how we win and scale enterprise retail partnerships.
Key Responsibilities1. Growth: Enterprise Acquisition & Market Shaping
Sales Velocity: Coach your AEs to bring in quality, high value opportunities, managing to a strong win rate and a short sales cycles
Anchor Account Strategy: Identify and win "anchor" retail accounts: national big-box, global grocery, and multi-banner retail conglomerates.
Solution Design: Position WorkWhile as a strategic solution for retail-specific labor volatility, including seasonal peak, store openings, and large-scale inventory cycles.
Complex MSAs: Support your AEs as they navigate multi-threaded enterprise sales cycles and complex procurement and legal hurdles typical of Fortune 500 retailers.
Strategic Positioning: Move the conversation from "transactional staffing" to "labor elasticity as a competitive advantage".
2. Retention: Operational & Technical Excellence
Fulfillment Oversight: Partner with WorkWhile’s Operations team to ensure 90%+ fill rates and high-quality, reliable workers.
Executive Multi-Threading: Build deep ties across Operations, HR, and IT.
Churn Mitigation: Proactively identify “at-risk” accounts through data analysis and executive touchpoints to ensure WorkWhile remains their primary staffing partner.
Data-Driven QBRs: Lead reviews focused on site-level performance, labor cost optimization, and turnover reduction metrics.
3. Expansion: Strategic Upselling
Wallet Share: Transition accounts from "seasonal support" to year-round labor partners across Store Ops, Last-Mile Fulfillment, and Distribution Centers, winning majority wallet share from other staffing providers.
Location Expansion: Lead the rollout of successful pilots from a single region or banner to the client’s nationwide location network.
Referral Loops: Incentivize and structure “land and expand” strategies where a win at one location opens doors to an entire brand portfolio.
4. Pod Leadership & GM Mentality
Team Mentorship: Lead and coach a team of Enterprise Account Executives and Account Managers.
P&L Ownership: Own the Retail vertical’s revenue, NDR, and segment profitability (CAC vs. LTV).
Cross-Functional Bridge: Act as the "voice of the retailer" for WorkWhile’s Product and Supply teams to ensure our roadmap meets enterprise retail needs.
Experience: 10+ years in enterprise sales or strategic partnerships, with 3+ years in a leadership role managing multi-disciplinary teams.
Retail Fluency: Deep experience in retail operations, warehousing and logistics. You understand:
Store-level operational realities and the "on-call" nature of retail.
Margin sensitivity and the impact of labor on P&L.
Omni-channel complexities (connecting store labor with fulfillment needs).
Full-Cycle Mindset: You think like a GM, caring as much about the long-term health and revenue growth as you do about the signed contract.
Executive Presence: Comfortable navigating C-suite stakeholders at Fortune 500 environments.
Leadership Style: A "Player-Coach" who can jump on a discovery call, support a QBR (Quarterly Business Review), and mentor an AE on a complex negotiation in the same day.
Net New Revenue: Annual Contract Value (ACV) of new enterprise MSAs.
Net Dollar Retention (NDR): Revenue growth within the existing retail portfolio.
Pod Profitability: Managing the CAC vs the LTV of the segment.
Benefits & Perks
Remote work
In-person company off-sites
Medical, dental, & vision coverage
Unlimited time off
401(k) with employer match
WFH stipend to support your home office needs
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!
What the Team is Saying
WorkWhile Compensation & Benefits Highlights
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Healthcare Strength — Healthcare is presented as strong for corporate roles with 100% employer-paid employee medical, dental, and vision premiums and generous family coverage. Platform workers also have free telehealth access and, for eligible W‑2 roles, an ICHRA allowance toward individual coverage.
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Leave & Time Off Breadth — Time off is broad for corporate employees with unlimited PTO and other leave provisions. Platform W‑2 workers also accrue paid sick time at one hour per 30 hours worked.
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Parental & Family Support — Parental leave is presented as generous for corporate staff, with 16 weeks for birthing parents and 12 weeks for non‑birthing parents. Family support also includes an onsite Mother’s Room.
WorkWhile Insights
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What We Do
WorkWhile is an AI-powered next generation labor platform that helps businesses in light industrial, hospitality, and events achieve over 90% fill rates and reduce no-shows through AI and predictive machine learning. We ensure seamless shift execution with trained, on-demand workers supported by on-site leads, real-time performance monitoring, and a robust accountability system. Our worker-first model boosts retention through benefits like next-day pay, telehealth, and free upskilling, while our platform delivers real-time analytics and dedicated support for every client. By combining flexibility, reliability, and deep insights, WorkWhile helps businesses scale efficiently and stay competitive.
Why Work With Us
WorkWhile is a technology platform with product and engineering at its core. Founded by alumni from Google, Meta, Yahoo, and Airbnb, continuous innovation is our strategy. We are an AI-native company that doesn’t just adopt new technologies, we operationalize them at scale to solve real business challenges.
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WorkWhile Offices
Hybrid Workspace
Employees engage in a combination of remote and on-site work.
Our hybrid policy allows workers to work flexibly - either in person in one of our four hubs (San Francisco HQ, New York, Seattle, Toronto), or remote. We encourage employees coming in person to come 2-3x per week.
