Job Description

Title: OSS Shift Lead - 30323

Location: On-site, Chicago, IL (within 30 minutes of the city) – Full time 40hrs/week

Classification: W2 under Staffing Supplier

Contract Duration: April 27, 2026 – August 31, 2026

Compensation: $27.62/hour

Visa Sponsorship: Not provided

Position Overview

A dynamic operational team is seeking a highly reliable OSS Shift Lead to coordinate day-to-day staffing and operational flow for on-site staff (OSS) throughout Chicago. Acting as the “control tower” on shift, this individual ensures seamless shift coverage, rapid troubleshooting, and real-time communication across field and central operations.

Key Responsibilities

Shift Management & Staffing

• Assign OSS to scheduled shifts, ensuring full coverage across all active jobs.
• Monitor attendance, lateness, and no-shows; take immediate corrective action as needed.
• Manage real-time backfill of staffing gaps through reassignment or escalation.

Real-Time Operations Oversight

• Troubleshoot operational issues (e.g., late arrivals, setup delays, participant confusion) as they occur.
• Escalate critical or complex problems with clear context and solutions.

Communication Hub

• Serve as the main point of contact for all inbound/outbound communication with OSS during the shift.
• Respond promptly to OSS questions, issues, and status updates.
• Coordinate efficiently with internal teams (Ops, Support, Launchers, etc.) to maintain smooth operations.

Success Indicators

• All shifts are fully staffed with minimal last-minute adjustments.
• Clearly communicated assignments—OSS know exactly where to be and what to do.
• Issues are resolved quickly, often without needing escalation.
• Communication is fast, clear, and proactive.
• On-site participants consistently have a seamless experience.

Qualifications

• 1–3 years’ experience in operations, logistics, hospitality, or similarly fast-paced environments.
• Demonstrated strong, real-time decision-making and problem-solving abilities.
• Excellent written and verbal communication skills.
• Highly responsive, reliable, and able to manage several workflows simultaneously.

Nice to Have:

• Experience with dispatch, shift scheduling, or gig workforce management.
• Familiarity with last-mile logistics or on-demand service operations.

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