Implementation & Training Supervisor

The Role:

Crafty is seeking a driven Implementation and Training Supervisor to lead new client implementations and in-field employee training in the Chicago market. This role requires the individual to show up in person at our client sites, offices, and/or warehouses most days of the week (minimum of three, sometimes five), with flexibility to support new client launches on-site. Your key responsibilities include managing our flex team, operational execution for new client implementations, and ongoing training and development for both new hires and veteran team members.

You will manage multiple projects efficiently, identify process improvements, and ensure high client satisfaction. Success in this role requires adaptability, problem-solving skills, and the ability to lead a dynamic team with varying schedules. If you thrive in a fast-paced environment, enjoy leadership, and are passionate about delivering outstanding experiences, we want to hear from you!

Required Attributes

• Autonomous:
• • Takes ownership of new client launches, training programs, and team management.
  • Steps in to support on-site coverage or training when needed and available, especially when the Flex team reaches capacity, to protect the client experience.
  • Makes informed decisions, adapts to dynamic schedules, and proactively improves processes to drive operational efficiency, ensure successful implementations, and enhance both employee and client experiences.
• Operationally Sound:
• • Ensures seamless and efficient operations by overseeing and executing new client implementations, training programs, and team coordination, as showcased in high implementation scorecards.
  • Maintains a strong focus on resource allocation, planning and managing both advance and short-notice coverage for the market’s concierge team to ensure continuity and consistent service levels.
  • Proactively prepares for upcoming implementations, coordinating logistics, resources, and timelines well in advance to ensure smooth, on-time execution.
  • Prioritizes process adherence and continuous improvement, constantly reevaluating workflows to drive operational excellence and successful client outcomes.
• Client Obsessed:
• • Prioritizes understanding and exceeding client expectations, ensuring smooth implementations and seamless onboarding.
  • Brings enthusiasm, patience, and a problem-solving mindset to client interactions, driving satisfaction and long-term success.
  • Consistently achieves high client satisfaction in post-implementation surveys, using feedback to refine and improve the client experience.
• Problem Solver:
• • Evaluates challenges with a strategic mindset, identifying root causes and implementing practical, sustainable solutions that ensure smooth client implementations and long-term operational success.
• Cross-functional Collaborator:
• • Works across teams—including Fulfillment, Client Operations, Implementation, and People Operations—to ensure alignment, clear communication, and seamless execution.
  • Fosters a supportive, team-oriented environment through constructive problem-solving and a shared commitment to continuous improvement.
• Effective Communicator:
• • Communicates clearly and confidently across multiple channels, ensuring alignment and transparency with both clients and internal teams.
  • Sets expectations, provides guidance, and encourages open dialogue to drive successful implementations and training initiatives.
  • Serves as the primary on-site contact for clients during implementation setups, ensuring smooth execution and proactive support.
• Adaptable:
• • Adjusts to dynamic environments by proactively solving problems, refining strategies, and meeting evolving client and company needs.
  • Maintains a positive attitude while navigating change, continuously improving processes to ensure seamless implementations and overall team success.

Required Experience

• 3+ years of experience in a client/customer experience role
• 3+ years of experience managing a team
• Food & Beverage industry experience

Your Proficiencies

• Google Suite (Sheets, Docs, Slides)
• Project management platforms (Notion, Asana)
• Data visualization tools (Tableau)

Don’t meet all of the qualifications? We want you to consider all of your skills and…