Head of Field Operations

WorkWhile

1d•Hybrid

About The Position

WorkWhile deploys on-site shift leads at enterprise accounts across warehousing, events, and retail. These are high-volume, high-visibility environments where execution quality is directly tied to client retention and revenue. This role owns that execution. You will manage a team of Field Operations Managers, each of whom directly oversees a portfolio of shift leads across their market. You are accountable for shift lead fill reliability, on-site quality, and the health of our largest client relationships. The defining challenge of this role is scale. As WorkWhile grows, the complexity of managing a distributed on-site workforce across multiple verticals and markets compounds faster than any team can absorb manually. The person in this seat will be the architect of how a lean Field Operations team, armed with the right systems, data, and AI-enabled tools, can manage a large and growing on-site workforce without sacrificing quality. That means knowing what AI can do better than a human, what systems and processes to build, and where human judgment is irreplaceable and must be protected.

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

Nice To Haves

Experience designing or implementing AI-enabled workforce tools — scheduling, anomaly detection, performance scoring, or automated alerting
Background in staffing tech, gig economy platforms, or high-volume hourly workforce management
Experience across multiple workforce verticals — warehousing, events, retail, or similar
Familiarity with the commercial dynamics of on-site staffing — mark-up structures, ratio requirements, billing controls

Responsibilities

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 a 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