Head of Scheduling at a Reputable Company

We are now looking for a Head of Scheduling to own our end-to-end guide scheduling strategy and execution. This role is responsible for designing how we plan, allocate, and adjust guide coverage across all cities while live operations are running.

The Role in One Line

Own the strategy, systems, and day-to-day execution of guide scheduling across all markets, ensuring consistent coverage, operational stability, and predictable guide experience at scale.

What You Will Do

Scheduling Strategy and Ownership

• Own the global scheduling model for guides across all North American cities
• Define scheduling principles, rules, and guardrails that balance flexibility, reliability, and cost
• Continuously improve how far ahead schedules are planned and how changes are managed

Workforce Planning and Forecasting

• Partner with Operations and Demand teams to translate bookings and forecasts into staffing plans
• Set coverage targets by city, day, and time window
• Identify gaps, risks, and overcoverage early and course correct proactively

Real-Time Scheduling Governance

• Oversee live schedule adjustments during operations, including coverage gaps, no shows, and last-minute changes.
• Set escalation rules and decision frameworks for real-time coordination teams.
• Ensure consistency and fairness in how scheduling changes are handled across markets.

Team Leadership and Development

• Lead and develop the Scheduling team, including coordinators and analysts
• Set clear expectations, workflows, and performance standards
• Coach the team to operate calmly, decisively, and consistently under pressure

Systems, Tools, and Process Improvement

• Own scheduling tools and workflows including WhenIWork and internal systems
• Partner with Tech and Ops to improve automation, visibility, and data quality
• Document SOPs and continuously refine scheduling playbooks

Performance Monitoring and Reporting

• Track key scheduling metrics, including coverage rate, late changes, no shows, and guide utilization
• Surface insights and trends to senior Operations leadership
• Use data to drive improvements in guide experience and operational efficiency

What You Bring

Must Have

• Strong experience in workforce scheduling, operations planning, or real-time operations
• Proven ability to manage complexity across multiple cities or teams
• Excellent judgment under pressure with a structured decision-making approach
• Comfort with data, spreadsheets, and operational dashboards
• Clear and confident communication skills with the ability to influence cross-functional partners

Nice to Have

• Experience in travel, tourism, mobility, logistics, or marketplace operations
• Hands-on experience with workforce management tools
• Experience leading distributed or remote teams