Senior Manager, Scaled Live Training & Enablement

Toast; United States; Hybrid; USD 149,000 - 238,000; Full time

Job summary

Toast is seeking a Senior Manager to lead the SMB/Core live training team across the US and international markets. Scale the program while ensuring quality and adherence to facilitation standards, tying training to reduced customer friction and product adoption.

You will partner with Learning Design, Customer Enablement, Go To Market and Product to evolve the strategy with new tech, while focusing on scalable delivery and measurable customer outcomes.

Qualifications

• 8+ years of experience in B2B Customer Training, Enablement, Instructional Program Management, Learning Design or related discipline in a fast-paced environment.
• 4+ years of people management experience with coaching and development of trainers or enablement professionals.
• Experience managing a live/virtual training calendar and team capacity at scale.
• Deep expertise in instructional strategy and curriculum evolution to close proficiency and adoption gaps.
• Experience influencing senior stakeholders and driving cross-functional alignment for outcomes.
• Strong data/analytics skills guiding prioritization and program design.
• Familiarity with AI tools in training and a genuine interest in future strategy.
• Comfort operating in a fast-paced, ambiguous environment, both strategically and tactically.

Responsibilities

• Own the strategic vision and operational excellence of the SMB/Core training team, ensuring scalable and impactful training models.
• Lead the evolution of training programs to align with company initiatives, including international expansion.
• Create, assess, and maintain team processes and standards.
• Partner with Enablement Program Managers to drive training impact on usage, growth and retention.
• Build, lead and coach a high-performing trainer team with clear objectives, metrics and development.
• Manage capacity and delivery logistics to ensure reliable access to live training.
• Act as escalation and quality owner for live training delivery and customer experience.

Skills

Strategic leadership

Team management

Live/virtual training

Data-driven

Cross-functional collaboration

AI strategy

Tools

Zoom

Articulate

LMS platforms

Job description

Toast is seeking a Senior Manager to lead the SMB/Core live training team across the US and international markets. Scale the program while ensuring quality and adherence to facilitation standards, tying training to reduced customer friction and product adoption.

You will partner with Learning Design, Customer Enablement, Go To Market and Product to evolve the strategy with new tech, while focusing on scalable delivery and measurable customer outcomes.