About The Position

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.

Requirements

  • 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.

Responsibilities

  • 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".
  • 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.
  • 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.
  • 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.

Benefits

  • 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
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