Job Description
Russell Tobin & Associates is currently seeking an Operations Support Specialist Shift Leader to work for one of our mobile delivery service providers. Prior experience working in marketplace ops, gig workforce management, or hospitality would be ideal!
Apply now for immediate consideration!
Contract: 4 + months – likely to be extended
Location: Chicago, IL
Pay Rate: $22 - 25 per hour on W2
Operations Support Specialist (OSS) Shift Lead
Role Overview
The OSS Shift Lead is the operational backbone of the day-to-day shift.
This role owns real-time coordination of OSS (On-Site Staff), ensuring shifts are properly staffed, issues are resolved quickly, and communication flows seamlessly between the field and central operations.
You are the "control tower” during your shift — responsible for keeping operations running smoothly and stepping in when things go off track.
Qualifications
• 1–3 years in operations, logistics, hospitality, or similar fast-paced environments
• Strong real-time decision-making and problem-solving skills
• Excellent communication (written + verbal), Comfortable managing multiple workflows simultaneously
• Highly reliable and responsive
Nice to Have
• Experience in dispatch, shift scheduling, or gig workforce management
• Familiarity with last-mile logistics or on-demand operations
Key Responsibilities
1. Shift Management & Staffing Assign OSS to shifts and ensure full coverage across all active jobs Monitor attendance, lateness, and no-shows; take immediate corrective action
Backfill gaps in real-time by reassigning or escalating
2. Real-Time Operations Oversight Troubleshoot issues (e.g., late arrivals, setup problems, participant confusion) Escalate critical issues with clear context and proposed solutions
3. Communication Hub Serve as the primary point of contact for all inbound/outbound OSS communication during shift
• Respond to OSS questions, issues, and updates quickly and clearly
• Coordinate with internal teams (Ops, Support, Launchers etc.) as needed What Good Looks Like All shifts are fully staffed with minimal last-minute scrambling OSS know exactly where to be and what to do Issues are resolved quickly without escalation when possible
• Communication is fast, clear, and proactive Participants have a seamless experience on-site
Must be authorized to work in the United States
Why Join?
This role offers the chance to impact financial performance, gain exposure to strong leadership principles, and grow professionally—all with competitive pay and potential for long-term engagement.
Russell Tobin offers eligible employees comprehensive healthcare coverage (medical, dental, and vision plans), supplemental coverage (accident insurance, critical illness insurance and hospital indemnity), a 401(k)-retirement savings, life & disability insurance, an employee assistance program, identity theft protection, legal support, auto and home insurance, pet insurance, and employee discounts with some preferred vendors
Apply now for immediate consideration!
Contract: 4 + months – likely to be extended
Location: Chicago, IL
Pay Rate: $22 - 25 per hour on W2
Operations Support Specialist (OSS) Shift Lead
Role Overview
The OSS Shift Lead is the operational backbone of the day-to-day shift.
This role owns real-time coordination of OSS (On-Site Staff), ensuring shifts are properly staffed, issues are resolved quickly, and communication flows seamlessly between the field and central operations.
You are the "control tower” during your shift — responsible for keeping operations running smoothly and stepping in when things go off track.
Qualifications
• 1–3 years in operations, logistics, hospitality, or similar fast-paced environments
• Strong real-time decision-making and problem-solving skills
• Excellent communication (written + verbal), Comfortable managing multiple workflows simultaneously
• Highly reliable and responsive
Nice to Have
• Experience in dispatch, shift scheduling, or gig workforce management
• Familiarity with last-mile logistics or on-demand operations
Key Responsibilities
1. Shift Management & Staffing Assign OSS to shifts and ensure full coverage across all active jobs Monitor attendance, lateness, and no-shows; take immediate corrective action
Backfill gaps in real-time by reassigning or escalating
2. Real-Time Operations Oversight Troubleshoot issues (e.g., late arrivals, setup problems, participant confusion) Escalate critical issues with clear context and proposed solutions
3. Communication Hub Serve as the primary point of contact for all inbound/outbound OSS communication during shift
• Respond to OSS questions, issues, and updates quickly and clearly
• Coordinate with internal teams (Ops, Support, Launchers etc.) as needed What Good Looks Like All shifts are fully staffed with minimal last-minute scrambling OSS know exactly where to be and what to do Issues are resolved quickly without escalation when possible
• Communication is fast, clear, and proactive Participants have a seamless experience on-site
Must be authorized to work in the United States
Why Join?
This role offers the chance to impact financial performance, gain exposure to strong leadership principles, and grow professionally—all with competitive pay and potential for long-term engagement.
Russell Tobin offers eligible employees comprehensive healthcare coverage (medical, dental, and vision plans), supplemental coverage (accident insurance, critical illness insurance and hospital indemnity), a 401(k)-retirement savings, life & disability insurance, an employee assistance program, identity theft protection, legal support, auto and home insurance, pet insurance, and employee discounts with some preferred vendors
💡 Quick Summary
Seeking a career-building opportunity? The Operational Specialist position is now open for candidates interested in the Operations Executive Jobs sector. This role in Chicago offers a professional environment and growth potential.
Requirement Snapshot: Candidates should possess basic communication skills, a proactive attitude, and the ability to work in a team. Experience in Operations Executive Jobs is a plus.