Training program manager Jobs in Chicago, IL

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Job Description: Program Manager – SM2 Program

Position Overview:

The Program Manager owns an SM2 (Amazon) regional territory end-to-end as we launch and hold sites together across the country. This first hire is Chicago-based and serves as the senior regional lead on the program team — effectively the program’s number two in the field. Reporting to the VP Program Operations, you will run client escalations, partner and restaurant onboarding, launch support, and remote site auditing.

The role is built for remote management. Whether each Program Manager lives near their cluster for year-one troubleshooting is still an open question, so comfort operating remotely — and traveling to sites only when genuinely warranted, rather than by default — is essential. You won’t just manage accounts; you’ll help build the systems that let the program scale.

What You’ll Be Doing:

• Own a regional territory end-to-end, starting with Chicago / Central
• Manage client escalations and keep launches on schedule
• Onboard restaurant and operating partners and manage partner issues
• Build and run remote site-audit systems (the priority year-one build)
• Coordinate field-troubleshooting resources without defaulting to flying in
• Serve as a senior regional lead on the SM2 program team, supporting the Program Lead and helping mentor future Program Manager hires (East / West / Central)
• Analyze and track key operational and usage metrics to make informed decisions and present strategic recommendations
• Monitor account-level financial health across your territory, including receivables and payables, and resolve issues promptly

Requirements

Who You Are:

• You have 4–6 years of experience in multi-site operations, account management, or regional operations, ideally in a service, hospitality, or tech-enabled environment
• You have strong remote-management discipline and are comfortable owning a regional/national territory and building process from scratch
• You’re highly data-driven, capable of pulling insights from usage reports, KPIs, and dashboards to inform decisions
• You’re organized and detail-oriented, managing multiple locations, priorities, and timelines at once
• You have experience hiring, training, and managing staff, with a supportive, accountability-driven leadership style
• You’re a strong communicator who can coordinate stakeholders and contribute to executive-facing meetings
• You’re willing to travel to sites when genuinely warranted, not by default
• You’re comfortable in Excel and internal tools, and you use data to solve problems and drive improvements

Benefits

What We’ll Hook You Up With:

• Competitive market salary and stock options, based on experience
• Comprehensive health, dental and vision plans
• 401k retirement plan with company match
• Paid maternity and parental leave benefits
• Flexible spending accounts
• Company issued laptop
• Daily subsidized lunch program (ours!) and free food and beverages in the office
• A fulfilling, challenging adventure of a work experience

Must be authorized to work in the United States on a full-time basis. No recruiters please.

The salary range for this role is $80,000–$115,000 base. The salary is dependent on a number of factors including but not limited to: work experience, training, location and skills.