WorkWhile
Head of Field Operations
Remote (US)
Sponsorship not specifiedDetected 34 days ago
Data ScienceAccount ManagementPerformance ManagementCadence
About the role
- These are high-volume, high-visibility environments where execution quality is directly tied to client retention and revenue.
- 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.
Responsibilities
- 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
- You will manage a team of Field Operations Managers, each of whom directly oversees a portfolio of shift leads across their market.
- Set and enforce the cadence by which Field Operations Managers maintain direct contact with leads and clients at every major account
- Deliver proactive monthly performance summaries to key accounts
- 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
- 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
- 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
- Define what high performance looks like at every stage of the lead lifecycle and build the systems to measure it
Requirements
- 4+ years in field operations, workforce management, or staffing, and managing distributed teams across multiple accounts and verticals
- Experience thinking about the commercial implications of operational decisions: you understand how deployment choices affect margin
- Strong client communicator: you have managed difficult conversations with diverse stakeholders
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
- 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
- In-person company off-sites
Skills
- Define the framework for when an account requires a dedicated on-site presence versus a remotely-managed model
Compensation
- 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
- 401(k) with employer match
- 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!
Benefits
- Own the health and size of the
- Run weekly performance reviews with all FOMs - account health, incidents, lead flags, commercial exposure
- Field Execution and Account Health
- pre-shift confirmations, clock-in anomaly detection, attendance pattern recognition, early leave flagging, performance scoring
- shift lead fill reliability, on-site quality, and the health of our largest client relationships.
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