Head of Field Operations

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 telehealth 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.

WorkWhile is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.

About the Role

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.

What You'll Own

Field Execution and Account Health

• 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

Commercial Accountability

• 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

AI-Enabled Operations and Scale

• 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

Lead Talent and Development

• 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

Team Performance

• 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

What We're Looking For

• 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 Have

• 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

Why This Role

• You will own the function that most directly determines whether WorkWhile's largest clients stay or leave

• Real commercial accountability from day one

• You will architect how WorkWhile scales field operations through AI and systems, not headcount. This is a genuinely novel problem with no obvious playbook

• You will work closely with COO with significant visibility across Operations, Product, and GTM

• WorkWhile is at an inflection point, and what you build in the next 12 months will define how this function operates for years

Compensation & 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

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!