Head of Field Operations

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WorkWhile

WebsiteLinkedInAll Job Openings

51 - 200 employees

👥 HR Tech

☁️ SaaS

🤖 Artificial Intelligence

💰 $23M Series B - WorkWhile on 2025-06

HR Tech • SaaS • Artificial Intelligence

WorkWhile is an AI-powered labor and workforce-management platform that connects businesses with vetted, certified frontline workers for on-demand, temporary, and long-term assignments. The platform provides a full-stack, SaaS workforce solution—matching and scheduling talent across industries like warehousing, logistics, manufacturing, hospitality, facilities, and retail—while offering features such as background checks, certification support, next-day pay, a worker app, and machine-learning driven real-time labor management and insights. WorkWhile positions itself as a single source of truth for dynamic staffing needs, enabling businesses to scale flexibly with transparent pricing and data-driven staffing decisions.

📋 Description

• Own on-site quality standards across all active enterprise accounts — warehousing, events, and retail • Ensure every account is staffed reliably, on time, and at the ratio the client expects — before the shift starts • Set and enforce the cadence by which Field Operations Managers maintain direct contact with leads and clients at every major account • Ensure incidents are identified, logged, triaged, and communicated to clients and account management teams • Deliver proactive monthly performance summaries to key accounts • Own the commercial implications of on-site investments — every lead deployed represents an investment, and this role ensures that cost is justified by the value it delivers to the account • Define the framework for when an account requires a dedicated on-site presence versus a remotely-managed model • Partner with Account Management and Finance to ensure field deployment decisions are commercially sound • Lead WorkWhile's build of an AI-enabled field operations model — the core question is how one Field Operations Manager can effectively oversee a workforce of many • Define what AI and automated systems should own: pre-shift confirmations, clock-in anomaly detection, attendance pattern recognition, early leave flagging, performance scoring • Define what humans must own: relationship-critical conversations, judgment calls under pressure, client escalations, lead development • Translate the above into a clear product and systems roadmap in partnership with Engineering and Data Science • Build the monitoring infrastructure that surfaces the right information to the right person at the right time — so the team is acting on signals, not searching for them • Own the health and size of the shift lead talent pool across all accounts and verticals • Build a standardized lead qualification, onboarding, and performance scoring program that works across warehousing, events, and retail • Develop a compliant, sustainable on-site talent model — one that attracts reliable leads, retains top performers, and removes underperformers with consistency • Define what high performance looks like at every stage of the lead lifecycle and build the systems to measure it • Manage and develop a team of Field Operations Managers across TriState, Mid-West, and West Coast markets • Run weekly performance reviews with all FOMs — account health, incidents, lead flags, commercial exposure

🎯 Requirements

• 4+ years in field operations, workforce management, or staffing, and managing distributed teams across multiple accounts and verticals • Demonstrated track record owning account health and on-site quality at scale • Experience thinking about the commercial implications of operational decisions: you understand how deployment choices affect margin • Genuine curiosity about how AI and automation can augment a lean operations team — you don't need to build it yourself, but you need to know what to ask for and why • Fluent in data: you use dashboards to find problems early, not to report results after the fact • Strong client communicator: you have managed difficult conversations with diverse stakeholders • Comfortable building structure where little exists: this function is growing and you will shape how it scales.

🏖️ Benefits

• Competitive base salary + equity in a high-growth, venture-backed company • Hybrid work culture with office hubs in SF, NY, Seattle & Toronto. • In-person company off-sites • Medical, dental & vision coverage • Unlimited PTO • 401(k) with employer match • WFH stipend to support your home office setup