Head of Field Operations

WorkWhile

Head of Field Operations at WorkWhile managing distributed teams across various accounts. Driving operational excellence and implementing AI-enabled solutions for workforce management.

Posted 6/17/2026full-timeRemote • 🇺🇸 United StatesLeadWebsite

About the role

Key responsibilities & impact

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

What you’ll need

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

Comp & perks

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

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

field operationsworkforce managementstaffingaccount health managementperformance scoringdata analysisAI integrationautomationlead qualificationonboarding

Soft Skills

client communicationteam managementproblem-solvingrelationship managementjudgment under pressurecuriosityadaptabilityleadershiporganizational skillsperformance management