Training Implementation Manager Jobs in Chicago, IL

Note to Candidates:
We meticulously craft our job descriptions to clearly define the skills necessary for success and the expected performance level of the role, resulting in detailed content. Our goal is to ensure the description accurately reflects the job you will perform. We value your input and look forward to hearing what you think about the format in the interview process.
This hybrid role requires the individual to show up in person at our client sites, offices, and/or warehouses most days of the week, and will report directly to the Market Operations Manager.
Who We Are:
Crafty elevates workplace food and beverage programs with enhanced services managed in one innovative, centralized platform. Founded in 2015, our mission is to help companies craft better workplaces. From DraftKings to Robinhood to Zillow, we work with the world's biggest brands to foster a culture of employee connectivity and productivity. Headquartered in Chicago, with offices in New York and the Bay Area, Crafty manages food and beverage programs across 300+ offices, serving more than 300,000 employees per month.
Our commitment to crafting better workplaces starts from within. We are a team of passionate, resourceful, and hard-working trailblazers who love what we do. Our expertise spans technology, food and beverage operations, client success, fulfillment and more. At Crafty, our people are our greatest asset, because it's our people who foster a culture that makes our company a place worth being part of. And of course, the snacks are the cherry on top!
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 experiences - both professional and personal- that would make you successful in this role. Although some qualifications are essential, others can be attained with time. We believe diverse perspectives, upbringings, and knowledge contribute to our strong company culture and we encourage you to apply.
Role Goals:
Goal #1: Optimize Resource Allocation & Operational Efficiency

• Through 2026, reduce market allocated time within flex operations 5% on a quarter-over-quarter basis - measured by the Market Profitability Tableau report - while maintaining team overtime at or below 90 minutes per week per flex team member, tracked via timecards, in support of Crafty's Market Profit goal.

Goal #2: Deliver a Seamless First 90-Day Client Experience

• Through 2026, achieve a 98% average on implementation scorecards and maintain a first 90-day escalation rate of 10% or below across all client implementations directly assigned to the Implementation & Training Supervisor - scorecard tracked monthly via Tableau and escalation rate measured quarterly via the HubSpot escalation pipeline.

Goal #3: New Hire Training Quality & Readiness

• Through 2026, ensure that 90% or more of new F&B Associates trained by the Implementation & Training Supervisor complete the full Market Ops Academy onboarding curriculum within 30 days of their start date and meet or exceed expectations at their 90-day performance check-in - tracked via training completion records in Notion and Lattice performance reviews, reviewed monthly.

Goal #4 (AI): Develop & Contribute to Corporate Implementation Content

• By EOY 2026, leverage AI tools to develop and contribute visual merchandising standards and structured implementation content that feeds Crafty's corporate implementation team - enabling consistent onboarding quality and site audit readiness across all markets - targeting 95%+ visual standards compliance across all new client launches, measured by implementation scorecard scores reviewed monthly.

What we offer:
Our people mean everything to us. When you join Crafty, you're joining a team of passionate, smart, and supportive people who work incredibly hard and have a good time along the way.
We are proud to offer a compensation package that includes our Crafty healthcare plan, covering primary health, dental, and vision plans, an automatic 401k contribution, paid time off, equipment certification courses, and parental leave. And, of course, it also includes Crafty-grade snacks, beverages, and fun events!
Lastly, this role offers a special opportunity: to have a major hand in shaping the future of a young, flourishing company. Your creativity, ambition, and work will steer the direction of our successes.
Our compensation amount for this role is targeted at $55,000 - $70,000 per year in Chicago. Final offer amounts are determined by multiple factors including cost of living based on location, candidate experience and expertise, and may vary from the amounts listed above.
Crafty provides equal employment opportunities (EEO) to all employees and applicants for employment without discriminating against race, color, religion, sex, sexual orientation, national origin, age, disability or genetics.