Senior Manager, Customer Training

Toast creates technology to help restaurants and local businesses succeed in a digital world, helping business owners operate, increase sales, engage customers, and keep employees happy.

This role, reporting to the Director of Customer Enablement, provides direct operational leadership and strategic oversight of Toast's high-volume, 1:many live training team, supporting the full customer lifecycle for our SMB and Core customer base across the US and International markets. As a Senior Manager, you will scale this high-impact program while ensuring quality and adherence to facilitation standards across all virtual offerings, tying training directly to reduced customer friction and product adoption, all while helping shape the future of live customer instruction at Toast.

This leader partners closely with Customer Enablement Programs, Learning Design, Customer Success, Go To Market, and Product teams to ensure our live training strategy evolves alongside technological advancements in training and education, while always putting our customers’ needs first.  

A day in the life (Responsibilities)

Program Strategy & Scalability

• 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.

Team Leadership & Development

• 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.

Cross-Functional Alignment & Program Insights

• 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.

AI Strategy & Innovation

• 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.

What you'll need to thrive (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.

Nice to Haves:

• 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.

AI at Toast

At Toast, one of our company values is that we're hungry to build and learn. We believe learning new AI tools empowers us to build for our customers faster, more independently, and with higher quality. We provide these tools across all disciplines, from Engineering and Product to Sales and Support, and are inspired by how our Toasters are already driving real value with them. The people who thrive here are those who embrace changes that let us build more for our customers; it’s a core part of our culture.

Our Total Rewards Philosophy

We strive to provide competitive compensation and benefits programs that help to attract, retain, and motivate the best and brightest people in our industry. Our total rewards package goes beyond great earnings potential and provides the means to a healthy lifestyle with the flexibility to meet Toasters’ changing needs. Learn more about our benefits at https://careers.toasttab.com/toast-benefits.