workwhilejobs - Head of Field Operations
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 • 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
Benefits
• 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 • 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!
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