Senior Manager, Customer Training

Toast creates technology that helps restaurants and local businesses succeed in a digital world. The Senior Manager, Customer Training provides strategic and operational leadership for Toast's high-volume virtual customer training team, scaling programs, developing trainers, ensuring delivery quality, aligning cross-functional stakeholders, and incorporating AI into customer education.

Responsibilities:

• Own the strategic vision and operational excellence of the SMB/Core training team, ensuring training models remain scalable and impactful as Toast grows
• Lead the evolution of training programs to align with broader company strategic initiatives, such as international expansion
• Create, assess, and maintain team processes and standards
• Partner with Enablement Program Managers to ensure the training program drives customer usage and supports customer growth and retention
• Build, lead and maintain a high-performing team of Trainers by overseeing team objectives, key results, standards, projects, and metrics
• Develop the team through coaching, mentoring, performance management, and upskilling
• Manage capacity and utilization, ensuring the team’s time is focused on the highest-impact work and that delivery capacity scales with demand
• Oversee the training schedule and delivery logistics to ensure consistent, reliable access to live training for our customers
• Serve as the escalation point and quality owner for live training delivery, ensuring adherence to facilitation standards and a consistently excellent customer experience
• Collaborate directly with leaders across GTM, Marketing, Customer Success, and Product to ensure live training supports key cross-functional goals and a seamless customer experience
• Partner with Learning Design and Customer Enablement Programs to identify efficiency gaps and translate product changes and customer friction points into new or evolved training content
• Own data-driven readouts to stakeholders on training metrics, program progress, and impact, and oversee the data infrastructure behind those insights alongside our Analytics team
• Represent training in cross-functional planning, influencing senior stakeholders to ensure training strategy aligns with broader company priorities
• Define and evolve Toast's strategy for incorporating AI into customer training, including AI-assisted content development and in-class tools, ensuring the program stays ahead of how AI reshapes instructor-led education
• Pilot and evaluate emerging AI training tools that meaningfully improve program quality or scale

Requirements:

• Minimum of 8 years of experience in B2B Customer Training, Enablement, Instructional Program Management, Learning Design or a related discipline within a fast-paced, high-output environment
• 4+ years of people management experience, with a proven ability to coach, develop, and inspire trainers or enablement professionals
• Demonstrated experience managing a live/virtual training calendar and team capacity at scale, balancing delivery volume with program quality
• Deep expertise in instructional strategy, with a strong understanding of how to design and evolve curriculum to solve specific customer proficiency and adoption gaps
• Demonstrated experience influencing senior stakeholders and driving cross-functional alignment to deliver measurable customer outcomes
• Strong data and analytical skills, with experience using performance and customer usage data to guide prioritization and program design
• Familiarity with how AI tools can enhance live training delivery, content development, or trainer coaching, with genuine interest in helping shape how AI is incorporated into the team's future strategy
• Confident working in a fast-paced, ever-changing environment with ambiguity, effectively operating both strategically and tactically
• Experience managing a remote, distributed, multi-region/multi-country training team
• Experience piloting or scaling AI-assisted training tools
• Technical familiarity with virtual classroom and LMS platforms (e.g., Zoom, Articulate, or similar)
• Familiar with and empathetic to the restaurant customer experience and the unique operational workflows of restaurant operators