JOBSEARCHER

Operations Supervisor

JackpotWoburn, MAApril 12th, 2026
About the Role: Our Operations team is critical to our success and we are looking for a diligent, passionate Operations Supervisor to serve as our operational shift lead, supervise our Operations Associates, and act as additional support to our Operations Manager. This role is non-exempt, based on-site in our Woburn, Massachusetts location. Shifts are Tuesday to Saturday 2:30 pm - 11:00 pm. Hours may be subject to change as we open and monitor our business needs. This is the perfect opportunity if you love overseeing operations, mentoring team members, are interested in growing your career at a start-up, and playing a key role in growing a business! What You’ll Do: Lead and ensure successful day-to-day lottery processing operations by overseeing and training a team of Operation Associates, proactively making recommendations for operational improvements, and providing general technical support Serve as the first point of contact for our Operations Associates and support escalations in the absence of the Operations Manager including facility issues, product outages, and staffing gaps Support back-end operations and general quality control by maintaining ticket equipment, ensuring the integrity and streamlining of processes, and monitoring execution of processes by team members Prepare SOS (Start of Shift) & EOS (End of Shift) reports on a daily, weekly, and monthly basis; report shift performance metrics and escalate issues to Operations Manager Oversee retail operations, including, sales, inventory, cash mgmt, EOS draw reconciliation Assist with other various ad-hoc duties and projects as needed You Ideally Have: Junior level supervisory/lead experience Prior experience in retail, warehouse, or logistics operations Medium-level technological know-how with the ability to troubleshoot and solve basic technical issues with equipment, operate basic systems and platforms, etc. The ability to lift up to 40 pounds as needed About You: You have grit, tenacity, and what people describe to be a “get it done” mentality. You don’t believe any task is too big or too small for you You are known for your ability to pivot on the fly with changing priorities and remain calm under pressure You don’t mind if there isn't an existing playbook for you to follow; you are resourceful and self-reliant Your team members describe you as available, helpful, and a problem solver. You feel proud when you’re able to help others succeed in their roles You have a high attention to detail and are organized in how you work and get things done You fully own and are committed to your work. You don’t believe in cutting corners and it shows in the quality of your work One of Jackpot’s core values is Lifelong Learning. We don’t believe we are ever finished products and strongly believe in growing and developing to improve ourselves. If what you’ve read so far sounds exciting but your experience doesn’t quite match what we’re looking for, we strongly encourage you to apply anyway! We are committed to building a diverse, inclusive team where everyone can feel proud to contribute to. What We Can Offer You: $22 - $26/hr hourly pay rate (~$45-55k) Benefits on par with leading, progressive tech companies (think 100% employee-only coverage, monthly HSA contribution, etc.) A commitment to career development, mentorship, and growth A culture of trust and accountability Job Type: Full-time Pay: $22.00 - $26.00 per hour Expected hours: 40 per week Benefits: 401(k) Dental insurance Employee assistance program Health insurance Health savings account Life insurance Paid time off Parental leave Vision insurance Schedule: 8 hour shift Ability to Relocate: Woburn, MA: Relocate before starting work (Required) Work Location: In person