At a glance
- Experience
- 4+ years experience
- Workplace
- Remote
- Location
- Remote
About the role
- 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.
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.
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.
Preferred qualifications
- 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.
Workplace
- Remote; USA
Skills
- Zoom
- Articulate
